6773:
1617:
64:
395:
254:
80:
54:
89:
1135:
1130:
1140:
1125:
8002:
1231:
6755:
1227:
7966:
6764:
2470:
7990:
1813:, electrophiles attack at the alpha position. The selectivity for alpha over beta substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be drawn, of which four preserve an aromatic ring. For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic.
2089:
7978:
1406:
1656:
2434:(wetting agents) that effectively disperse colloidal systems in aqueous media. The major commercial applications are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and in the textile and fabric industry, which uses the wetting and defoaming properties of ANS for bleaching and dyeing operations.
1230:
1646:
1232:
1578:
The molecule is planar, like benzene. Unlike benzene, the carbonâcarbon bonds in naphthalene are not of the same length. The bonds C1âC2, C3âC4, C5âC6 and C7âC8 are about 1.37 Ă
(137 pm) in length, whereas the other carbonâcarbon bonds are about 1.42 Ă
(142 pm) long. This difference, established by
1569:
nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon atom adjacent to a shared one. The shared carbon atoms are labeled 4a (between 4 and 5) and 8a (between 8 and 1).
2111:
Naphthalene is the most abundant single component of coal tar. The composition of coal tar varies with coal type and processing, but typical coal tar is about 10% naphthalene by weight. In industrial practice,
1248:
4508:
1627:
across the plane of the shared carbon pair, as well as across the plane that bisects bonds C2-C3 and C6-C7, and across the plane of the carbon atoms. Thus there are two sets of equivalent hydrogen atoms: the
2679:, naphthalene is listed as "known to the State to cause cancer". A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing naphthalene has been identified.
1148:
2396:, precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals. They are also used as dispersants in synthetic and natural rubbers, in agricultural
4076:
1105:
3655:
John Kidd (1821). "Observations on
Naphthalene, a peculiar substance resembling a concrete essential oil, which is produced during the decomposition of coal tar, by exposure to a red heat".
3612:
Amoore JE, Hautala E (1983). "Odor as an aid to chemical safety: Odor thresholds compared with threshold limit values and volatiles for 214 industrial chemicals in air and water dilution".
2171:
Inc., Ruetgers Canada Inc. and
Recochem Inc., and the primary petroleum producer is Monument Chemical Inc. In Western Europe the well-known producers are Koppers, Ruetgers, and Deza. In
3826:
Dieter Cremer; Thomas
Schmidt; Charles W. Bock (1985). "Theoretical determination of molecular structure and conformation. 14. Is bicyclodecapentaene aromatic or antiaromatic?".
2675:; and that hemolytic anemia (described above) can occur in children and infants after oral or inhalation exposure or after maternal exposure during pregnancy. Under California's
2317:
Molten naphthalene provides an excellent solubilizing medium for poorly soluble aromatic compounds. In many cases it is more efficient than other high-boiling solvents, such as
2140:
to isolate naphthalene. The crude naphthalene resulting from this process is about 95% naphthalene by weight. The chief impurities are the sulfur-containing aromatic compound
2621:(NTP) held an experiment where male and female rats and mice were exposed to naphthalene vapors on weekdays for two years. Both male and female rats exhibited evidence of
7315:
7085:
7045:
6537:
3783:
Cruickshank, D. W. J.; Sparks, R. A. (18 October 1960). "Experimental and
Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons".
1911:
The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. These 1,8-dilithio derivatives are precursors to a host of
4499:
3751:
1233:
7246:
7221:
7211:
1703:. The resistivity drops more than a thousandfold on melting, to about 4 à 10 Ω m. Both in the liquid and in the solid, the resistivity depends on temperature as
1241:
7617:
6945:
6886:
6794:
5375:
4957:
4896:
7706:
7522:
7457:
7397:
7325:
7231:
7125:
6995:
6950:
6621:
4293:
3598:
3576:
2703:
2156:(< 2%). Petroleum-derived naphthalene is usually purer than that derived from coal tar. Where required, crude naphthalene can be further purified by
1346:
7786:
7251:
7095:
7065:
5365:
4472:
4080:
7181:
7161:
6834:
5360:
4881:
7206:
5347:
4868:
4127:
M.A. Filatov; A.V. Cheprakov (2011). "The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole".
1419:
4939:
3960:
1522:(a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar). Naphthalene's chemical formula was determined by
4094:
K. Komatsua; Y. Murataa; N. Sugitaa; et al. (1993). "Use of naphthalene as a solvent for selective formation of the 1:1 DielsâAlder adduct of C
6844:
6546:
3249:
3165:
3986:
van
Soolingen J, de Lang RJ, den Besten R, et al. (1995). "A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene".
7201:
6530:
5387:
4908:
1255:
6871:
5433:
2285:. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many
7417:
6814:
5448:
5443:
5428:
5013:
2695:
6965:
5517:
5486:
5265:
5255:
5140:
3268:
2571:
444:
6876:
5522:
5501:
5496:
5280:
5275:
5270:
5260:
5155:
5150:
5145:
5135:
4801:
2652:
2254:
Naphthalene is used mainly as a precursor to derivative chemicals. The single largest use of naphthalene is the industrial production of
1514:
cited these two disclosures and then described many of this substance's properties and the means of its production. He proposed the name
4612:
6523:
4207:
7744:
7060:
4530:
2349:
53:
2687:
2544:
Several uses stem from naphthalene's high volatility: it is used to create artificial pores in the manufacture of high-porosity
7276:
7035:
6955:
4642:
1036:
1616:
4333:
3514:
3338:
3321:
3233:
1826:
1814:
987:
63:
7657:
1770:, naphthalene reacts more readily than benzene. For example, chlorination and bromination of naphthalene proceeds without a
1194:
3744:
1645:
3467:
3438:
4212:
2533:
1014:
8042:
7909:
3969:
1414:
2160:
from any of a variety of solvents, resulting in 99% naphthalene by weight, referred to as 80 °C (melting point).
1565:
The eight carbon atoms that are not shared by the two rings carry one hydrogen atom each. For purpose of the standard
79:
8037:
7809:
2656:
409:
3854:
113:
white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
3696:
2574:, from which over 400 million people suffer. Humans, in particular children, have developed the condition known as
1426:
7934:
6118:
5567:
1640:
are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position.
1559:
1471:
1082:
8052:
6109:
4461:
4301:
2549:
2416:
1825:
as the thermodynamic product. The 1-isomer forms predominantly at 25 °C, and the 2-isomer at 160 °C.
1068:
4378:
88:
7859:
3418:
2219:
2157:
2108:, but present-day production is mainly from coal tar. Approximately 1.3 million tons are produced annually.
7894:
1884:
1188:
352:
249:
1139:
7090:
6427:
3133:
2728:, the use of naphthalene in mothballs is forbidden. Danger to human health and the common use of natural
2691:
2618:
2385:
1822:
1818:
1787:
373:
17:
1134:
211:
4635:
3723:
3217:
2707:
2699:
1671:
1370:
1357:
1129:
1502:
In the early 1820s, two separate reports described a white solid with a pungent odor derived from the
7849:
7844:
7025:
2711:
867:
261:
4362:
4208:"New propulsion system using the key ingredient in moth balls could propel satellites through space"
3360:
2633:
of the nose. Female mice exhibited some evidence of carcinogenesis based on increased incidences of
2582:, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may cause
7889:
6260:
2345:
2309:, and in museum storage-drawers and cupboards to protect the contents from attack by insect pests.
2100:. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy
1278:
390:
3402:
7969:
5027:
3184:
2514:
2137:
2073:
791:
159:
1124:
7824:
6789:
6699:
6576:
6571:
5977:
4791:
963:
4032:
3544:
3504:
8047:
8027:
7879:
7854:
7492:
7110:
6657:
6321:
6316:
6038:
5972:
4628:
4129:
3214:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2561:
2401:
1783:
1767:
1608:
1302:
1162:
1117:
739:
101:
8032:
7940:
7924:
7549:
6920:
6891:
6772:
6596:
6306:
6301:
6296:
6291:
6214:
5556:
5355:
4606:
4584:
4323:
4169:
3913:
3866:
3792:
2427:
2334:
803:
616:
361:
4411:
3428:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-24)
8:
7884:
7864:
7677:
7367:
6855:
6719:
6694:
6662:
6581:
6244:
5884:
4597:
4100:
3326:
3037:
3004:
2971:
2578:, after ingesting mothballs or deodorant blocks containing naphthalene. Symptoms include
2405:
2282:
1795:
1775:
1584:
1511:
1098:
586:
231:
125:
4298:
NTP Technical
Reports 410 and 500, available from NTP: Long-Term Abstracts & Reports
4173:
3917:
3870:
3796:
3396:
2714:
at 15 ppm (75 mg/m). Naphthalene's minimum odor threshold is 0.084 ppm for humans.
2552:; and it has been explored as a sublimable propellant for cold gas satellite thrusters.
394:
253:
191:
135:
7982:
7904:
7874:
7819:
7696:
7672:
7171:
7105:
6970:
6930:
6781:
6744:
6704:
6683:
6626:
6601:
6362:
6102:
6071:
6028:
4886:
4876:
4350:
4253:
4236:
3808:
3672:
3637:
3243:
3070:
2634:
2369:
2361:
2255:
2242:
2025:
2017:
1924:
1779:
1624:
1479:
891:
171:
4113:
3901:
1923:
With alkali metals, naphthalene forms the dark blue-green radical anion salts such as
7929:
7512:
7412:
7382:
7300:
7040:
6925:
6881:
6829:
6636:
6631:
6563:
6423:
6199:
5962:
5934:
5777:
5537:
5532:
5370:
4891:
4329:
4258:
4058:
3965:
3958:
Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and
Hydronaphthalenes".
3929:
3882:
3629:
3510:
3334:
3229:
2579:
2458:
2200:
2153:
2117:
1749:
is 0.73 in the solid. However, the solid shows semiconducting character below 100 K.
1663:
1600:
1588:
1580:
1551:
861:
6515:
3812:
3676:
3641:
2116:
of coal tar yields an oil containing about 50% naphthalene, along with twelve other
1558:
if they share two or more atoms.) As such, naphthalene is classified as a benzenoid
1478:
with a characteristic odor that is detectable at concentrations as low as 0.08
8006:
7994:
7914:
7814:
7719:
7667:
7100:
6975:
6940:
6861:
6849:
6809:
6714:
6647:
6413:
6209:
6204:
6087:
5926:
4248:
4187:
4177:
4138:
4109:
4048:
3995:
3921:
3874:
3835:
3800:
3785:
Proceedings of the Royal
Society A: Mathematical, Physical and Engineering Sciences
3705:
3664:
3621:
3221:
2806:
2771:
2764:
2575:
2454:
2442:
2348:
adduct. The aromatization of hydroporphyrins has been achieved using a solution of
2223:
2133:
2121:
1912:
1442:
911:
822:
623:
561:
467:
4578:
4281:
2388:
and sulfonates are useful. Naphthalenesulfonic acids are used in the synthesis of
1180:
7602:
7577:
7115:
7055:
6839:
6739:
6724:
6709:
6616:
6606:
6076:
6033:
5942:
5816:
4781:
4771:
4382:
4053:
2318:
2183:, dedicated naphthalene and phenol makers INKOR, Yenakievsky Metallurgy plant in
1803:
1531:
1523:
1291:
594:
280:
4013:
3225:
2717:
Mothballs and other products containing naphthalene have been banned within the
2710:
at 10 ppm (50 mg/m) over an eight-hour time-weighted average, as well as a
1086:
325:
7839:
7804:
7587:
7477:
7442:
7427:
7362:
7357:
7256:
7156:
7075:
7050:
7015:
6960:
6935:
6804:
6652:
6463:
6458:
6372:
6341:
6275:
6270:
6163:
6007:
6002:
5967:
5918:
5824:
4796:
4786:
3925:
3475:
3446:
2718:
2676:
2567:
2545:
2236:
2172:
2141:
1810:
1692:
Pure crystalline naphthalene is a moderate insulator at room temperature, with
1397:
769:
752:
609:
4590:
4436:
4142:
3999:
3572:
2740:
The partial list of naphthalene derivatives includes the following compounds:
2655:(IARC) classifies naphthalene as possibly carcinogenic to humans and animals (
2281:, although its use has largely been replaced in favor of alternatives such as
1328:
8021:
7869:
7724:
7607:
7582:
7563:
7507:
7387:
7345:
7340:
7080:
7070:
7030:
6905:
6799:
6754:
6729:
6611:
6591:
6095:
5684:
5491:
5481:
4977:
3933:
3886:
3709:
3540:
2630:
2164:
1880:
1799:
944:
548:
534:
242:
4182:
4157:
3590:
1535:
1202:
7945:
7799:
7652:
7592:
7572:
7544:
7472:
7352:
7335:
7290:
7241:
7146:
6866:
6819:
6667:
6408:
6357:
6239:
6224:
6183:
6158:
5790:
5754:
5650:
5423:
5413:
5322:
5312:
5302:
4843:
4833:
4823:
4394:
4262:
4093:
4062:
3804:
3668:
3625:
2622:
2525:
2489:
2477:
2450:
2326:
2322:
2113:
2105:
2077:
1763:
1604:
1503:
725:
4572:
3825:
3633:
3220:. 2014. pp. 13, 35, 204, 207, 221â222, 302, 457, 461, 469, 601, 650.
1254:
7919:
7829:
7794:
7687:
7662:
7502:
7407:
7377:
7261:
7176:
7166:
6896:
6824:
6382:
6367:
6265:
5838:
5795:
5768:
5702:
5665:
5438:
5418:
5405:
5337:
5332:
5327:
5317:
5307:
5294:
5125:
4858:
4853:
4848:
4838:
4828:
4815:
4651:
4276:
3902:"Observation of the Band-Hopping Transition for Electrons in Naphthalene"
2521:
2473:
2373:
2365:
1944:
1693:
1592:
1483:
1267:
875:
665:
32:
3839:
1240:
7834:
7776:
7739:
7714:
7612:
7422:
7285:
6311:
6280:
6168:
5897:
5785:
5589:
5476:
5466:
5395:
5130:
4952:
4947:
4922:
4776:
4766:
4192:
3179:
3175:
2875:
2702:
at 10 ppm (50 mg/m) over an eight-hour time-weighted average. The
2638:
2529:
2510:
2431:
2397:
2393:
2389:
2341:
2290:
2240:
produce naphthalene among a range of volatile organic compounds, while
2231:
2188:
2176:
1247:
1090:
721:
701:
685:
681:
661:
641:
580:
489:
262:
222:
3985:
3878:
1790:
conditions, naphthalene can also be easily alkylated by reaction with
1782:, respectively. Likewise, whereas both benzene and naphthalene can be
7766:
7631:
7467:
7271:
7151:
7005:
6980:
6504:
6494:
6489:
6418:
6326:
6234:
6178:
5902:
5640:
5609:
5599:
5594:
5471:
5199:
4987:
4982:
4761:
3330:
3170:
2583:
2409:
2294:
2101:
2069:
1771:
1094:
841:
4156:
Tsifakis, Dimitrios; Charles, Christine; Boswell, Rod (2020-09-23).
3691:
1396:
Except where otherwise noted, data are given for materials in their
7734:
7646:
7447:
7310:
7295:
7266:
7135:
6910:
6734:
6678:
6672:
6641:
6586:
6554:
6499:
6453:
6443:
6433:
6403:
6387:
6377:
6331:
6219:
6173:
6132:
6066:
6061:
5871:
5863:
5855:
5735:
5727:
5719:
5670:
5655:
5645:
5635:
5630:
5604:
5527:
5239:
5219:
5069:
4997:
4992:
4972:
4375:
3957:
3156:
2660:
2607:
2595:
2591:
2504:
2496:
2446:
2344:
is conveniently conducted in refluxing naphthalene to give the 1:1
2278:
2274:
2259:
2227:
2211:
2204:
2097:
2021:
1973:
1948:
1883:
is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by
1507:
1491:
1458:
1213:
300:
36:
4605:
4500:"Holy straight bananas â now the Eurocrats are banning moth balls"
3570:
1206:
158:
7899:
7729:
7682:
7641:
7597:
7539:
7534:
7497:
7487:
7482:
7437:
7432:
7372:
7305:
7196:
7191:
7141:
7020:
7010:
6763:
6468:
6448:
6438:
6137:
6023:
5997:
5847:
5692:
5625:
5224:
5214:
5204:
5094:
5084:
5074:
4962:
4928:
4916:
4730:
4720:
4710:
4700:
4325:
IARC Monographs on the
Evaluation of Carcinogenic Risks to Humans
3160:
3147:
2729:
2641:
2626:
2500:
2485:
2438:
2306:
2222:, possibly produced by the termite as a repellant against "ants,
2184:
2168:
1977:
1667:
1547:
1527:
1519:
1487:
1486:
hydrocarbon, naphthalene's structure consists of a fused pair of
1475:
645:
634:
630:
598:
590:
520:
312:
28:
2570:, most commonly in people with the inherited condition known as
2548:; it is used in engineering studies of heat transfer using mass
2408:
are used as precursors and to form pharmaceutical salts such as
1546:
A naphthalene molecule can be viewed as the fusion of a pair of
7950:
7771:
7753:
7216:
7186:
6688:
6336:
6229:
5892:
5811:
5711:
5660:
5234:
5229:
5209:
5169:
5109:
5104:
5099:
5089:
5079:
5040:
4967:
4745:
4740:
4735:
4725:
4715:
4705:
4670:
4620:
4031:
Daisy BH, Strobel GA, Castillo U, et al. (November 2002).
3509:. New York: Springer Science+Business Media, Inc. p. 288.
3152:
2668:
2587:
2566:
Exposure to large amounts of naphthalene may damage or destroy
2430:(ANS) are used in many industrial applications as nondetergent
2330:
2302:
2180:
2149:
2145:
2129:
1791:
1738:
1637:
1447:
1198:
705:
202:
4395:"Scientists May Have Solved Mystery Of Carcinogenic Mothballs"
2469:
2449:. They are produced by treating naphthalenesulfonic acid with
2088:
6985:
6915:
6484:
5576:
5542:
5458:
3595:
Immediately Dangerous to Life or Health Concentrations (IDLH)
3421:
in Linstrom, Peter J.; Mallard, William G. (eds.);
2725:
2672:
2611:
2603:
2599:
2298:
1871:
Further sulfonation give di-, tri-, and tetrasulfonic acids.
1700:
1596:
1566:
336:
182:
148:
4437:"CDC - NIOSH Pocket Guide to Chemical Hazards - Naphthalene"
3759:
Naphthalene is a PAH that is produced commercially in the US
3401:(2nd ed.). New York: D. Van Nostrand Company. pp.
1587:
model in naphthalene and in particular, with the theorem of
378:
3274:. United States Environmental Protection Agency. 2014-04-23
2861:
2648:, while male mice exhibited no evidence of carcinogenesis.
2645:
2360:
The single largest use of naphthalene is the production of
2286:
2215:
2125:
2068:
This reaction is the basis of the main use of naphthalene.
1383:
932:α = 90°, ÎČ = 122.92°, Îł = 90°
510:
291:
4126:
3423:
2520:
Substituted naphthalenes serve as pharmaceuticals such as
2495:
Hydrogenation of naphthalene gives tetrahydronaphthalene (
1666:
of naphthalene that have two fused aromatic rings include
2664:
2610:(yellow coloration of the skin due to dysfunction of the
2420:
1697:
1655:
1176:
4237:"Association of naphthalene with acute hemolytic anemia"
4616:. Vol. 19 (11th ed.). 1911. pp. 167â168.
4158:"Naphthalene as a Cubesat Cold Gas Thruster Propellant"
2659:). The IARC also points out that acute exposure causes
2072:
can also be effected using conventional stoichiometric
1976:. Further hydrogenation yields decahydronaphthalene or
4155:
2293:
uses of naphthalene include use in soil as a fumigant
6545:
3599:
National Institute for Occupational Safety and Health
3577:
National Institute for Occupational Safety and Health
2704:
National Institute for Occupational Safety and Health
2175:, naphthalene is produced by a variety of integrated
1940:. The naphthalene anions are strong reducing agents.
6117:
4531:"Council warned against use of poisonous moth balls"
4030:
2517:, which are useful as nonvolatile liquids for inks.
57:
Skeletal formula and numbering system of naphthalene
2572:
glucose-6-phosphate dehydrogenase (G6PD) deficiency
1829:to give the 1- and 2-sulfonic acid occurs readily:
4593:âCDC â NIOSH Pocket Guide to Chemical Hazards
4498:
4385:, Office of Environmental Health Hazard Assessment
4033:"Naphthalene, an insect repellent, is produced by
3900:Schein, L. B.; Duke, C. B.; McGhie, A. R. (1978).
1172:
3782:
2513:of naphthalene with propylene gives a mixture of
8019:
3899:
3269:"Ambient Water Quality Criteria for Naphthalene"
3166:List of interstellar and circumstellar molecules
2507:. Tetralin is used as a hydrogen-donor solvent.
2379:
2258:, although more phthalic anhydride is made from
2194:
1591:. This theorem would describe naphthalene as an
1490:rings. It is the main ingredient of traditional
324:
4669:
4557:ćœćĄéąç»èŽžćăć«çéšć
łäșćæąçäș§ćéćźèäžžæćĄäœżçšæšèć¶ćçéç„ïŒćœç»èŽžè°ïŒ1993ïŒ64ć·ïŒ
4416:Environmental Health Association of Nova Scotia
3689:
2419:are precursors for synthesis of many synthetic
1757:
1229:
553:217.97 °C (424.35 °F; 491.12 K)
418:InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
134:
3961:Ullmann's Encyclopedia of Industrial Chemistry
428:InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
6531:
6103:
4636:
3611:
3506:Structure and Chemistry of Crystalline Solids
3398:Solubility of Inorganic and Organic Compounds
3395:Seidell, Atherton; Linke, William F. (1919).
2696:Occupational Safety and Health Administration
2210:Trace amounts of naphthalene are produced by
2179:complexes (Severstal, Evraz, Mechel, MMK) in
1947:under high pressure in the presence of metal
1607:), which is consistent with two of its three
1168:
541:80.26 °C (176.47 °F; 353.41 K)
4234:
3692:"Studien ĂŒber die s. g. aromatischen SĂ€uren"
3426:, NIST Standard Reference Database Number 69
3394:
3248:: CS1 maint: DOI inactive as of June 2024 (
2404:plates. Naphthalenedisulfonic acids such as
2120:. This oil, after being washed with aqueous
1632:positions, numbered 1, 4, 5, and 8, and the
1623:Because of this resonance, the molecule has
4601:in the Pesticide Properties DataBase (PPDB)
3354:
3352:
3350:
3263:
3261:
3259:
2653:International Agency for Research on Cancer
1745:is absolute temperature (K). The parameter
1677:The point group symmetry of naphthalene is
539:78.2 °C (172.8 °F; 351.3 K)
6538:
6524:
6110:
6096:
4643:
4629:
3953:
3951:
3949:
3947:
3945:
3943:
2735:
1918:
1687:
393:
252:
230:
4252:
4191:
4181:
4052:
3745:"Polycyclic Aromatic Hydrocarbons (PAHs)"
3654:
3503:Douglas, Bodie E.; Ho, Shih-Ming (2007).
3502:
2445:used for the production of high strength
2246:produces naphthalene almost exclusively.
1737:is the Boltzmann constant (8.617 Ă 10 eV/
1670:, which has a 5â7 fused ring system, and
1377:TWA 10 ppm (50 mg/m) ST 15 ppm (75 mg/m)
360:
4496:
4490:
4014:"Termite 'mothball' keep insects at bay"
3893:
3852:
3846:
3724:"Ueber die Constitution des Naphthalins"
3571:NIOSH Pocket Guide to Chemical Hazards.
3536:
3534:
3532:
3530:
3528:
3526:
3358:
3347:
3256:
3206:
2468:
2464:
2364:, which is an intermediate used to make
2277:. It was once the primary ingredient in
2087:
1654:
1518:, as it had been derived from a kind of
3940:
3566:
3564:
3562:
3498:
3496:
3494:
3492:
2376:polymers used in paints and varnishes.
389:
14:
8020:
4575:âNational Pesticide Information Center
4412:"Mothballs, air fresheners and cancer"
3414:
3412:
3390:
3388:
3386:
3384:
3382:
3380:
3314:
3312:
3310:
3308:
3103:1,2,7-Trimethylnaphthalene (Sapotalin)
2488:are produced from naphthalene. Useful
1951:to give 1,2,3,4-tetrahydronaphthalene(
1752:
1541:
1286:525 °C (977 °F; 798 K)
243:
6519:
6091:
4624:
4404:
3523:
3439:"Thermal Conductivity of Naphthalene"
3322:CRC Handbook of Chemistry and Physics
3306:
3304:
3302:
3300:
3298:
3296:
3294:
3292:
3290:
3288:
1573:
1272:80 °C (176 °F; 353 K)
515:Strong odor of coal tar or mothballs
421:Key: UFWIBTONFRDIAS-UHFFFAOYSA-N
210:
190:
4528:
4522:
3559:
3489:
3318:
2503:), which are used as low-volatility
2132:), and with sulfuric acid to remove
1526:in 1826. The structure of two fused
4294:"NTP Technical Reports 410 and 500"
4213:Australian Broadcasting Corporation
4077:"Summary of Possum Repellent Study"
3726:(On the structure of naphthalene),
3409:
3377:
2534:nonsteroidal anti-inflammatory drug
1674:which has a fused 4â8 ring system.
431:Key: UFWIBTONFRDIAS-UHFFFAOYAC
315:
299:
67:Ball-and-stick model of naphthalene
24:
7910:Nexus for Exoplanet System Science
4587:âmostly on toxicity of naphthalene
4529:Gray, Kerrina (17 November 2013).
4254:10.1111/j.1553-2712.2000.tb01889.x
3468:"Dynamic Viscosity of Naphthalene"
3285:
2732:are cited as reasons for the ban.
2453:, followed by neutralization with
2355:
1225:
62:
52:
25:
8064:
7810:Atomic and molecular astrophysics
6547:Molecules detected in outer space
4566:
3855:"Semiconductivity of Naphthalene"
3757:from the original on 2014-11-30.
2555:
2096:Most naphthalene is derived from
1309:10 ppm (TWA), 15 ppm (STEL)
8000:
7988:
7976:
7965:
7964:
6771:
6762:
6753:
6119:Polycyclic aromatic hydrocarbons
4650:
4497:Alderson, Andrew (15 Nov 2008).
3728:Annalen der Chemie und Pharmacie
3697:Annalen der Chemie und Pharmacie
1644:
1615:
1404:
1138:
1133:
1128:
1123:
479:
87:
78:
7935:Polycyclic aromatic hydrocarbon
4548:
4511:from the original on 2022-01-12
4478:from the original on 2016-10-14
4454:
4429:
4388:
4369:
4316:
4286:
4269:
4235:Santucci K, Shah B (Jan 2000).
4228:
4200:
4149:
4120:
4087:
4069:
4024:
4006:
3979:
3859:The Journal of Chemical Physics
3819:
3776:
3764:
3737:
3716:
3683:
3648:
3605:
3583:
3550:
3187:(classic naphthalene synthesis)
2492:include naphthoxyacetic acids.
2273:Naphthalene has been used as a
1636:positions, 2, 3, 6, and 7. Two
1560:polycyclic aromatic hydrocarbon
1472:polycyclic aromatic hydrocarbon
1400:(at 25 °C , 100 kPa).
3460:
3431:
3197:
2417:aminonaphthalenesulfonic acids
2203:are the major constituents of
2187:and ArcelorMittal Temirtau in
1879:Analogous to the synthesis of
1733:(eV) are constant parameters,
1069:Occupational safety and health
473:
13:
1:
7860:Extraterrestrial liquid water
4114:10.1016/S0040-4039(00)61362-X
3191:
2694:to naphthalene exposure. The
2682:
2625:with increased incidences of
2539:
2380:Sulfonic acids and sulfonates
2220:Formosan subterranean termite
2195:Other sources and occurrences
2167:, the coal tar producers are
2083:
1874:
1351:(US health exposure limits):
1339:1200 mg/kg (guinea pig, oral)
505:White solid crystals/ flakes
4054:10.1099/00221287-148-11-3737
4037:, a novel endophytic fungus"
3359:Anatolievich, Kiper Ruslan.
3319:Lide, David R., ed. (2009).
2692:occupational exposure limits
2499:) and decahydronaphthalene (
2289:that attack textiles. Other
2230:worms". Some strains of the
2128:components (chiefly various
1758:Reactions with electrophiles
1337:490 mg/kg (rat, intravenous)
7:
7091:Protonated hydrogen cyanide
3556:Naphthalene carcinogenicity
3226:10.1039/9781849733069-FP001
3141:
3134:Naphthalene-2-sulfonic acid
2619:National Toxicology Program
2268:
1823:naphthalene-2-sulfonic acid
1821:as the kinetic product but
1819:naphthalene-1-sulfonic acid
1317:or concentration (LD, LC):
925: = 6.003 Ă
,
921: = 8.235 Ă
,
48:
10:
8069:
4020:. BBC News. April 8, 1998.
3926:10.1103/PhysRevLett.40.197
3853:Bornmann, John A. (1962).
3657:Philosophical Transactions
3218:Royal Society of Chemistry
2708:recommended exposure limit
2700:permissible exposure limit
2559:
2437:Some naphthalenesulfonate
2312:
2199:Naphthalene and its alkyl
1817:gives the "alpha" product
1534:in 1866, and confirmed by
1497:
26:
8043:IARC Group 2B carcinogens
7959:
7850:Earliest known life forms
7845:Diffuse interstellar band
7785:
7705:
7630:
7521:
7456:
7396:
7324:
7316:Protonated cyanoacetylene
7230:
7124:
7086:Protonated carbon dioxide
7046:Hydromagnesium isocyanide
6994:
6780:
6751:
6562:
6553:
6477:
6396:
6350:
6253:
6192:
6151:
6125:
6054:
6016:
5990:
5955:
5911:
5883:
5846:
5837:
5804:
5776:
5767:
5747:
5710:
5701:
5683:
5618:
5575:
5566:
5555:
5510:
5457:
5404:
5386:
5346:
5293:
5248:
5192:
5168:
5118:
5062:
5039:
5026:
5006:
4938:
4907:
4867:
4814:
4754:
4693:
4658:
4556:
4143:10.1016/j.tet.2011.01.052
4000:10.1080/00397919508015858
2712:short-term exposure limit
2386:naphthalenesulfonic acids
1595:benzene unit bonded to a
1583:, is consistent with the
1394:
1345:
1313:
1104:
1066:
1061:
937:
929: = 8.658 Ă
854:
460:
440:
405:
118:
110:
100:
95:
86:
77:
47:
8038:Hazardous air pollutants
7895:Ironâsulfur world theory
7890:Photodissociation region
7593:Methyl-cyano-diacetylene
6285:-Benzopyrene(Olympicene)
4581:âEPA Air Toxics Web Site
4537:. Newsquest (London) Ltd
4277:MedlinePlus Encyclopedia
3988:Synthetic Communications
3710:10.1002/jlac.18661370309
3690:Emil Erlenmeyer (1866).
3203:Naphthalene: trade names
1885:lithiumâhalogen exchange
1341:533 mg/kg (mouse, oral)
1189:Precautionary statements
816:0.1052 W/m·K (479.72 K)
27:Not to be confused with
7970:Category:Astrochemistry
7560:, fullerene, buckyball)
7247:Cyanobutadiynyl radical
7222:Silicon-carbide cluster
7212:Protonated formaldehyde
4613:EncyclopĂŠdia Britannica
4183:10.3389/fphy.2020.00389
3964:. Weinheim: Wiley-VCH.
3906:Physical Review Letters
3228:(inactive 2024-06-22).
3185:Wagner-Jauregg reaction
2736:Naphthalene derivatives
2515:diisopropylnaphthalenes
2249:
2138:fractional distillation
1919:Reduction and oxidation
1788:FriedelâCrafts reaction
1688:Electrical conductivity
1603:to it (at least in the
814:0.1152 W/m·K (418.37 K)
812:0.1174 W/m·K (400.22 K)
810:0.1219 W/m·K (372.22 K)
792:Magnetic susceptibility
7983:Outer space portal
7825:Circumstellar envelope
6790:Aluminium(I) hydroxide
6700:Phosphorus mononitride
6577:Aluminium monofluoride
6572:Aluminium monochloride
5978:1,3,5-Triheptylbenzene
4083:on September 28, 2013.
3805:10.1098/rspa.1960.0187
3669:10.1098/rstl.1821.0017
3626:10.1002/jat.2550030603
3424:NIST Chemistry WebBook
2481:
2428:naphthalene sulfonates
2136:components, undergoes
2093:
1768:substitution reactions
1660:
1530:rings was proposed by
1335:1800 mg/kg (rat, oral)
1236:
734:131.6 g/100 g (60 °C)
732:22.1 g/100 g (21.5 °C)
730:13.6 g/100 g (6.75 °C)
674:31.1 g/100 g (42.5 °C)
672:13.1 g/100 g (21.5 °C)
68:
58:
8053:Simple aromatic rings
7880:Interplanetary medium
7855:Extraterrestrial life
7493:Octatetraynyl radical
7111:Tricarbon monosulfide
6658:Magnesium monohydride
6261:Benzacephenanthrylene
5973:1,3,5-Triethylbenzene
4585:Naphthalene (PIM 363)
4282:Naphthalene poisoning
2562:Naphthalene poisoning
2472:
2465:Other derivative uses
2091:
1658:
1470:. It is the simplest
1364:TWA 10 ppm (50 mg/m)
1303:Threshold limit value
1235:
716:78.8 g/100 g (70 °C)
696:87.2 g/100 g (70 °C)
670:6.8 g/100 g (6.75 °C)
575:238.1 mg/L (73.4 °C)
529:0.9625 g/cm (100 °C)
66:
56:
8007:Chemistry portal
7995:Astronomy portal
7941:RNA world hypothesis
7925:PAH world hypothesis
7618:Heptatrienyl radical
7550:Buckminsterfullerene
7438:Methylcyanoacetylene
6946:Silicon carbonitride
6921:Methylidynephosphane
6887:Magnesium isocyanide
6795:Aluminium isocyanide
6597:Carbon monophosphide
5376:Isopropylcyclohexene
4958:Perhydrophenanthrene
4897:Isopropylcyclohexane
4162:Frontiers in Physics
2840:1-Naphthoyl chloride
2305:and animals such as
2214:and some species of
2152:(< 2%), and
1599:but not extensively
1218:(fire diamond)
804:Thermal conductivity
714:30.8 g/100 g (40 °C)
712:17.5 g/100 g (25 °C)
694:49.5 g/100 g (40 °C)
692:35.5 g/100 g (25 °C)
676:111 g/100 g (60 °C)
656:179 g/100 g (70 °C)
654:19.5 g/100 g (40 °C)
652:11.3 g/100 g (25 °C)
525:1.145 g/cm (15.5 °C)
7885:Interstellar medium
7865:Forbidden mechanism
7678:Hydrogen isocyanide
7368:Hexatriynyl radical
6951:c-Silicon dicarbide
6856:Hydrogen isocyanide
6720:Silicon monosulfide
6695:Phosphorus monoxide
6663:Methylidyne radical
6622:Fluoromethylidynium
6582:Aluminium(II) oxide
6245:Tricyclobutabenzene
6072:Alicyclic compounds
5885:Tetramethylbenzenes
4607:"Naphthalene"
4535:Your Local Guardian
4304:on October 24, 2004
4174:2020FrP.....8..389T
4101:Tetrahedron Letters
3918:1978PhRvL..40..197S
3871:1962JChPh..36.1691B
3840:10.1021/jo00215a018
3797:1960RSPSA.258..270C
3327:Boca Raton, Florida
3038:2-Chloronaphthalene
3005:1-Chloronaphthalene
2972:1-Fluoronaphthalene
2283:1,4-dichlorobenzene
2016:in the presence of
1943:Naphthalene can be
1776:1-chloronaphthalene
1753:Chemical properties
1672:Bicyclodecapentaene
1542:Physical properties
1538:three years later.
690:19.5 g/100 g (0 °C)
571:43.9 mg/L (34.5 °C)
562:Solubility in water
527:1.0253 g/cm (20 °C)
497: g·mol
172:Beilstein Reference
44:
7905:Molecules in stars
7875:Intergalactic dust
7820:Circumstellar dust
7762:Naphthalene cation
7697:Trihydrogen cation
7673:Hydrogen deuteride
7598:Methyltriacetylene
7433:Hexapentaenylidene
7252:E-Cyanomethanimine
7172:Cyclopropenylidene
7106:Tricarbon monoxide
7096:Silicon tricarbide
7066:Methylene amidogen
7056:Isothiocyanic acid
6971:Thioxoethenylidene
6931:Trihydrogen cation
6745:Titanium(II) oxide
6705:Potassium chloride
6684:Sulfur mononitride
6627:Helium hydride ion
6602:Carbon monosulfide
6029:Cyclopropenylidene
5366:Methylcyclopentene
5356:Methylcyclopropene
4887:Methylcyclopentane
4877:Methylcyclopropane
4381:2019-07-29 at the
4098:with anthracene".
4047:(Pt 11): 3737â41.
4035:Muscodor vitigenus
3773:, P-14.4 NUMBERING
3071:1-Bromonaphthalene
2937:1-Nitronaphthalene
2690:agencies have set
2482:
2400:, in dyes, and in
2370:polyvinyl chloride
2362:phthalic anhydride
2333:. The reaction of
2256:phthalic anhydride
2243:Muscodor vitigenus
2118:aromatic compounds
2106:petroleum refining
2094:
2026:phthalic anhydride
2018:vanadium pentoxide
1925:sodium naphthalene
1780:1-bromonaphthalene
1664:Structural isomers
1661:
1625:bilateral symmetry
1574:Molecular geometry
1427:Infobox references
1386:(Immediate danger)
1237:
850:0.217 cP (150 °C)
785:0.42438 L·atm/mol
710:5.5 g/100 g (0 °C)
69:
59:
42:
8015:
8014:
7930:Pseudo-panspermia
7626:
7625:
7573:Cyanodecapentayne
7513:N-Methylformamide
7488:Methyldiacetylene
7413:Aminoacetonitrile
7383:Methyl isocyanate
7301:Methyl isocyanide
7182:Isocyanoacetylene
7162:Cyanoformaldehyde
7041:Hydrogen peroxide
6926:Potassium cyanide
6882:Magnesium cyanide
6835:Disilicon carbide
6830:Dicarbon monoxide
6637:Hydrogen fluoride
6632:Hydrogen chloride
6513:
6512:
6424:Hexabenzocoronene
6307:Benzofluoranthene
6302:Benzofluoranthene
6297:Benzofluoranthene
6292:Benzofluoranthene
6215:Benzophenanthrene
6085:
6084:
6050:
6049:
5986:
5985:
5963:Hexamethylbenzene
5951:
5950:
5833:
5832:
5778:Trimethylbenzenes
5763:
5762:
5679:
5678:
5551:
5550:
5538:Cyclododecatriene
5533:Cyclooctatetraene
5371:Methylcyclohexene
5361:Methylcyclobutene
5348:Alkylcycloalkenes
5289:
5288:
5164:
5163:
5022:
5021:
4892:Methylcyclohexane
4882:Methylcyclobutane
4869:Alkylcycloalkanes
4810:
4809:
4335:978-92-832-1282-9
4216:. 8 December 2021
4137:(19): 3559â3566.
4108:(52): 8473â8476.
3994:(11): 1741â1744.
3879:10.1063/1.1732805
3834:(15): 2684â2688.
3791:(1293): 270â285.
3722:C. Graebe (1869)
3541:Sigma-Aldrich Co.
3516:978-0-387-26147-8
3340:978-1-4200-9084-0
3325:(90th ed.).
3235:978-0-85404-182-4
3216:. Cambridge: The
3139:
3138:
2459:calcium hydroxide
2443:superplasticizers
2402:leadâacid battery
2218:, as well as the
2158:recrystallization
2154:methylnaphthalene
2104:fractions during
1972:), also known as
1589:cross-conjugation
1581:X-ray diffraction
1552:organic chemistry
1476:crystalline solid
1474:, and is a white
1435:Chemical compound
1433:
1432:
1163:Hazard statements
1015:Gibbs free energy
862:Crystal structure
848:0.761 cP (100 °C)
763:2.5 kPa (100 °C)
573:80.9 mg/L (50 °C)
569:31.6 mg/L (25 °C)
374:CompTox Dashboard
160:Interactive image
73:
72:
16:(Redirected from
8060:
8005:
8004:
8003:
7993:
7992:
7991:
7981:
7980:
7979:
7968:
7967:
7915:Organic compound
7815:Chemical formula
7720:Dihydroxyacetone
7668:Hydrogen cyanide
7353:Cyanodiacetylene
7207:Propadienylidene
7101:Thioformaldehyde
6976:Titanium dioxide
6941:Sodium hydroxide
6862:Hydrogen sulfide
6850:Hydrogen cyanide
6810:Carbonyl sulfide
6775:
6766:
6757:
6715:Silicon monoxide
6648:Hydroxyl radical
6560:
6559:
6540:
6533:
6526:
6517:
6516:
6414:Diindenoperylene
6322:Dibenzanthracene
6317:Dibenzanthracene
6312:trans-Bicalicene
6112:
6105:
6098:
6089:
6088:
6042:-Propenylbenzene
5844:
5843:
5774:
5773:
5708:
5707:
5699:
5698:
5573:
5572:
5564:
5563:
5249:Branched alkynes
5190:
5189:
5119:Branched alkenes
5060:
5059:
5037:
5036:
4940:Polycycloalkanes
4925:(bicycloheptane)
4919:(bicyclopentane)
4755:Branched alkanes
4691:
4690:
4667:
4666:
4645:
4638:
4631:
4622:
4621:
4617:
4609:
4561:
4560:
4558:
4552:
4546:
4545:
4543:
4542:
4526:
4520:
4519:
4517:
4516:
4502:
4494:
4488:
4487:
4485:
4483:
4477:
4466:
4458:
4452:
4451:
4449:
4447:
4433:
4427:
4426:
4424:
4422:
4408:
4402:
4401:, June 20, 2006.
4392:
4386:
4373:
4367:
4366:
4360:
4356:
4354:
4346:
4344:
4342:
4320:
4314:
4313:
4311:
4309:
4300:. Archived from
4290:
4284:
4273:
4267:
4266:
4256:
4232:
4226:
4225:
4223:
4221:
4204:
4198:
4197:
4195:
4185:
4153:
4147:
4146:
4124:
4118:
4117:
4091:
4085:
4084:
4079:. Archived from
4073:
4067:
4066:
4056:
4028:
4022:
4021:
4010:
4004:
4003:
3983:
3977:
3975:
3955:
3938:
3937:
3897:
3891:
3890:
3865:(6): 1691â1692.
3850:
3844:
3843:
3823:
3817:
3816:
3780:
3774:
3768:
3762:
3761:
3756:
3749:
3741:
3735:
3720:
3714:
3713:
3687:
3681:
3680:
3652:
3646:
3645:
3609:
3603:
3602:
3587:
3581:
3580:
3568:
3557:
3554:
3548:
3538:
3521:
3520:
3500:
3487:
3486:
3484:
3483:
3474:. Archived from
3464:
3458:
3457:
3455:
3454:
3445:. Archived from
3435:
3429:
3416:
3407:
3406:
3392:
3375:
3374:
3372:
3371:
3356:
3345:
3344:
3316:
3283:
3282:
3280:
3279:
3273:
3265:
3254:
3253:
3247:
3239:
3210:
3204:
3201:
2908:1-Naphthaldehyde
2807:2-Naphthoic acid
2772:1-Naphthoic acid
2765:Refractive index
2749:Chemical formula
2743:
2742:
2576:hemolytic anemia
2455:sodium hydroxide
2406:Armstrong's acid
2352:in naphthalene.
2301:spaces to repel
2144:(< 2%),
2122:sodium hydroxide
2015:
2014:
2013:
2000:
1999:
1998:
1990:
1989:
1971:
1970:
1969:
1961:
1960:
1939:
1938:
1913:peri-naphthalene
1899:Br + BuLi â C
1867:
1648:
1619:
1469:
1468:
1467:
1457:
1456:
1443:organic compound
1417:
1411:
1408:
1407:
1292:Explosive limits
1257:
1250:
1243:
1228:
1208:
1204:
1200:
1196:
1182:
1178:
1174:
1170:
1142:
1137:
1132:
1127:
1093:. Dust can form
1053:
1026:
1004:
977:
953:
938:Thermochemistry
912:Lattice constant
905:
904:
846:0.964 cP (80 °C)
823:Refractive index
798:-91.9·10 cm/mol
761:0.93 kPa (80 °C)
650:5 g/100 g (0 °C)
595:Carboxylic acids
496:
481:
475:
468:Chemical formula
398:
397:
382:
380:
364:
328:
317:
303:
281:Gmelin Reference
264:
256:
245:
234:
214:
194:
162:
138:
91:
82:
49:
45:
41:
21:
8068:
8067:
8063:
8062:
8061:
8059:
8058:
8057:
8018:
8017:
8016:
8011:
8001:
7999:
7989:
7987:
7977:
7975:
7955:
7781:
7757:
7748:
7701:
7691:
7634:
7622:
7603:Propionaldehyde
7578:Ethylene glycol
7567:
7559:
7555:
7526:
7524:
7517:
7473:Cyanohexatriyne
7459:
7452:
7399:
7392:
7327:
7320:
7280:
7233:
7226:
7197:Methoxy radical
7127:
7120:
7116:Thiocyanic acid
6997:
6990:
6900:
6840:Ethynyl radical
6776:
6770:
6769:
6768:
6767:
6761:
6760:
6759:
6758:
6749:
6740:Sulfur monoxide
6725:Sodium chloride
6710:Silicon carbide
6617:Diatomic carbon
6607:Carbon monoxide
6549:
6544:
6514:
6509:
6478:General classes
6473:
6392:
6346:
6249:
6188:
6147:
6121:
6116:
6086:
6081:
6077:Petroleum jelly
6046:
6034:Phenylacetylene
6012:
5982:
5947:
5943:Isobutylbenzene
5907:
5879:
5829:
5800:
5759:
5743:
5697:
5675:
5614:
5558:
5547:
5506:
5453:
5400:
5382:
5342:
5285:
5244:
5186:
5178:
5172:
5160:
5114:
5056:
5049:
5043:
5032:
5030:
5018:
5002:
4934:
4931:(bicyclodecane)
4903:
4863:
4806:
4772:3-Methylpentane
4750:
4687:
4679:
4673:
4662:
4660:
4654:
4649:
4604:
4569:
4564:
4554:
4553:
4549:
4540:
4538:
4527:
4523:
4514:
4512:
4495:
4491:
4481:
4479:
4475:
4464:
4460:
4459:
4455:
4445:
4443:
4435:
4434:
4430:
4420:
4418:
4410:
4409:
4405:
4393:
4389:
4383:Wayback Machine
4374:
4370:
4358:
4357:
4348:
4347:
4340:
4338:
4336:
4322:
4321:
4317:
4307:
4305:
4292:
4291:
4287:
4274:
4270:
4233:
4229:
4219:
4217:
4206:
4205:
4201:
4154:
4150:
4125:
4121:
4097:
4092:
4088:
4075:
4074:
4070:
4029:
4025:
4012:
4011:
4007:
3984:
3980:
3972:
3956:
3941:
3898:
3894:
3851:
3847:
3824:
3820:
3781:
3777:
3769:
3765:
3754:
3747:
3743:
3742:
3738:
3721:
3717:
3688:
3684:
3653:
3649:
3610:
3606:
3589:
3588:
3584:
3569:
3560:
3555:
3551:
3539:
3524:
3517:
3501:
3490:
3481:
3479:
3466:
3465:
3461:
3452:
3450:
3437:
3436:
3432:
3417:
3410:
3393:
3378:
3369:
3367:
3357:
3348:
3341:
3317:
3286:
3277:
3275:
3271:
3267:
3266:
3257:
3241:
3240:
3236:
3212:
3211:
3207:
3202:
3198:
3194:
3144:
3113:
3109:
3082:
3078:
3049:
3045:
3016:
3012:
2983:
2979:
2951:
2947:
2943:
2918:
2914:
2887:
2883:
2850:
2846:
2822:
2818:
2814:
2787:
2783:
2779:
2738:
2685:
2568:red blood cells
2564:
2558:
2546:grinding wheels
2542:
2467:
2382:
2358:
2356:Derivative uses
2338:
2319:dichlorobenzene
2315:
2271:
2252:
2224:poisonous fungi
2197:
2086:
2063:
2059:
2055:
2051:
2047:
2043:
2039:
2035:
2012:
2009:
2008:
2007:
2005:
2004:Oxidation with
1997:
1994:
1993:
1992:
1988:
1985:
1984:
1983:
1981:
1968:
1965:
1964:
1963:
1959:
1956:
1955:
1954:
1952:
1937:
1934:
1933:
1932:
1930:
1921:
1906:
1902:
1898:
1894:
1877:
1865:
1861:
1857:
1853:
1849:
1845:
1841:
1837:
1833:
1804:phosphoric acid
1760:
1755:
1728:
1713:
1690:
1682:
1652:
1576:
1544:
1532:Emil Erlenmeyer
1524:Michael Faraday
1500:
1466:
1463:
1462:
1461:
1455:
1452:
1451:
1450:
1446:
1436:
1429:
1424:
1423:
1422: ?)
1413:
1409:
1405:
1401:
1387:
1374:
1361:
1340:
1338:
1336:
1332:
1326:
1306:
1283:
1280:
1262:
1261:
1260:
1259:
1252:
1245:
1238:
1234:
1226:
1191:
1165:
1151:
1120:
1079:
1057:-5156.3 kJ/mol
1054:
1051:
1045:
1041:
1038:
1037:Std enthalpy of
1030:201.585 kJ/mol
1027:
1021:
1017:
1005:
1002:
996:
992:
989:
988:Std enthalpy of
981:167.39 J/mol·K
978:
975:
968:
965:
957:165.72 J/mol·K
954:
947:
933:
930:
914:
903:
900:
899:
898:
894:
884:
878:
864:
849:
847:
833:
831:
815:
813:
811:
809:
795:
782:
780:
771:
762:
760:
759:23.6 Pa (30 °C)
758:
757:8.64 Pa (20 °C)
733:
731:
715:
713:
711:
695:
693:
691:
675:
673:
671:
655:
653:
651:
627:
620:
613:
606:
602:
574:
572:
570:
568:
567:19 mg/L (10 °C)
564:
554:
542:
540:
528:
526:
494:
484:
478:
470:
456:
453:
448:
447:
436:
433:
432:
429:
423:
422:
419:
413:
412:
401:
383:
376:
367:
347:
331:
318:
306:
283:
274:
237:
217:
197:
174:
165:
152:
141:
128:
114:
106:
40:
23:
22:
15:
12:
11:
5:
8066:
8056:
8055:
8050:
8045:
8040:
8035:
8030:
8013:
8012:
8010:
8009:
7997:
7985:
7973:
7960:
7957:
7956:
7954:
7953:
7948:
7943:
7938:
7932:
7927:
7922:
7917:
7912:
7907:
7902:
7897:
7892:
7887:
7882:
7877:
7872:
7867:
7862:
7857:
7852:
7847:
7842:
7840:Cosmochemistry
7837:
7832:
7827:
7822:
7817:
7812:
7807:
7805:Astrochemistry
7802:
7797:
7791:
7789:
7783:
7782:
7780:
7779:
7774:
7769:
7764:
7759:
7755:
7751:
7746:
7742:
7737:
7732:
7727:
7722:
7717:
7711:
7709:
7703:
7702:
7700:
7699:
7694:
7689:
7685:
7680:
7675:
7670:
7665:
7660:
7658:Formyl radical
7655:
7650:
7644:
7638:
7636:
7628:
7627:
7624:
7623:
7621:
7620:
7615:
7610:
7605:
7600:
7595:
7590:
7588:Methyl acetate
7585:
7580:
7575:
7570:
7565:
7561:
7557:
7553:
7547:
7542:
7537:
7531:
7529:
7519:
7518:
7516:
7515:
7510:
7505:
7500:
7495:
7490:
7485:
7480:
7478:Dimethyl ether
7475:
7470:
7464:
7462:
7454:
7453:
7451:
7450:
7445:
7443:Methyl formate
7440:
7435:
7430:
7428:Glycolaldehyde
7425:
7420:
7415:
7410:
7404:
7402:
7394:
7393:
7391:
7390:
7385:
7380:
7375:
7370:
7365:
7363:Glycolonitrile
7360:
7358:Ethylene oxide
7355:
7350:
7349:
7348:
7338:
7332:
7330:
7322:
7321:
7319:
7318:
7313:
7308:
7303:
7298:
7293:
7288:
7283:
7278:
7274:
7269:
7264:
7259:
7257:Cyclopropenone
7254:
7249:
7244:
7238:
7236:
7228:
7227:
7225:
7224:
7219:
7214:
7209:
7204:
7199:
7194:
7189:
7184:
7179:
7174:
7169:
7164:
7159:
7157:Cyanoacetylene
7154:
7149:
7144:
7139:
7132:
7130:
7122:
7121:
7119:
7118:
7113:
7108:
7103:
7098:
7093:
7088:
7083:
7078:
7076:Methyl radical
7073:
7068:
7063:
7058:
7053:
7051:Isocyanic acid
7048:
7043:
7038:
7033:
7028:
7023:
7018:
7016:Isocyanic acid
7013:
7008:
7002:
7000:
6992:
6991:
6989:
6988:
6983:
6978:
6973:
6968:
6963:
6961:Sulfur dioxide
6958:
6953:
6948:
6943:
6938:
6936:Sodium cyanide
6933:
6928:
6923:
6918:
6913:
6908:
6903:
6898:
6894:
6889:
6884:
6879:
6874:
6869:
6864:
6859:
6853:
6847:
6845:Formyl radical
6842:
6837:
6832:
6827:
6822:
6817:
6812:
6807:
6805:Carbon dioxide
6802:
6797:
6792:
6786:
6784:
6778:
6777:
6752:
6750:
6748:
6747:
6742:
6737:
6732:
6727:
6722:
6717:
6712:
6707:
6702:
6697:
6692:
6686:
6681:
6676:
6670:
6665:
6660:
6655:
6653:Iron(II) oxide
6650:
6645:
6639:
6634:
6629:
6624:
6619:
6614:
6609:
6604:
6599:
6594:
6589:
6584:
6579:
6574:
6568:
6566:
6557:
6551:
6550:
6543:
6542:
6535:
6528:
6520:
6511:
6510:
6508:
6507:
6502:
6497:
6492:
6487:
6481:
6479:
6475:
6474:
6472:
6471:
6466:
6464:Trinaphthylene
6461:
6459:Superphenalene
6456:
6451:
6446:
6441:
6436:
6431:
6421:
6416:
6411:
6406:
6400:
6398:
6394:
6393:
6391:
6390:
6385:
6380:
6375:
6373:Dibenzopyrenes
6370:
6365:
6360:
6354:
6352:
6348:
6347:
6345:
6344:
6342:Tetraphenylene
6339:
6334:
6329:
6324:
6319:
6314:
6309:
6304:
6299:
6294:
6289:
6288:
6287:
6278:
6273:
6263:
6257:
6255:
6251:
6250:
6248:
6247:
6242:
6237:
6232:
6227:
6222:
6217:
6212:
6207:
6202:
6200:Benzanthracene
6196:
6194:
6190:
6189:
6187:
6186:
6181:
6176:
6171:
6166:
6164:Acenaphthylene
6161:
6155:
6153:
6149:
6148:
6146:
6145:
6140:
6135:
6129:
6127:
6123:
6122:
6115:
6114:
6107:
6100:
6092:
6083:
6082:
6080:
6079:
6074:
6069:
6064:
6058:
6056:
6052:
6051:
6048:
6047:
6045:
6044:
6036:
6031:
6026:
6020:
6018:
6014:
6013:
6011:
6010:
6008:4-Vinyltoluene
6005:
6003:Divinylbenzene
6000:
5994:
5992:
5988:
5987:
5984:
5983:
5981:
5980:
5975:
5970:
5968:2-Phenylhexane
5965:
5959:
5957:
5953:
5952:
5949:
5948:
5946:
5945:
5940:
5932:
5924:
5915:
5913:
5909:
5908:
5906:
5905:
5900:
5895:
5889:
5887:
5881:
5880:
5878:
5877:
5869:
5861:
5852:
5850:
5841:
5835:
5834:
5831:
5830:
5828:
5827:
5825:4-Ethyltoluene
5822:
5820:-Propylbenzene
5814:
5808:
5806:
5802:
5801:
5799:
5798:
5793:
5788:
5782:
5780:
5771:
5765:
5764:
5761:
5760:
5758:
5757:
5751:
5749:
5745:
5744:
5742:
5741:
5733:
5725:
5716:
5714:
5705:
5696:
5695:
5689:
5687:
5681:
5680:
5677:
5676:
5674:
5673:
5668:
5663:
5658:
5653:
5648:
5643:
5638:
5633:
5628:
5622:
5620:
5616:
5615:
5613:
5612:
5607:
5602:
5597:
5592:
5587:
5581:
5579:
5570:
5561:
5553:
5552:
5549:
5548:
5546:
5545:
5540:
5535:
5530:
5525:
5520:
5514:
5512:
5508:
5507:
5505:
5504:
5499:
5494:
5489:
5484:
5479:
5474:
5469:
5463:
5461:
5455:
5454:
5452:
5451:
5446:
5441:
5436:
5431:
5426:
5421:
5416:
5410:
5408:
5402:
5401:
5399:
5398:
5392:
5390:
5388:Bicycloalkenes
5384:
5383:
5381:
5380:
5378:
5373:
5368:
5363:
5358:
5352:
5350:
5344:
5343:
5341:
5340:
5335:
5330:
5325:
5320:
5315:
5310:
5305:
5299:
5297:
5291:
5290:
5287:
5286:
5284:
5283:
5278:
5273:
5268:
5263:
5258:
5252:
5250:
5246:
5245:
5243:
5242:
5237:
5232:
5227:
5222:
5217:
5212:
5207:
5202:
5196:
5194:
5193:Linear alkynes
5187:
5180:
5174:
5166:
5165:
5162:
5161:
5159:
5158:
5153:
5148:
5143:
5138:
5133:
5128:
5122:
5120:
5116:
5115:
5113:
5112:
5107:
5102:
5097:
5092:
5087:
5082:
5077:
5072:
5066:
5064:
5063:Linear alkenes
5057:
5051:
5045:
5034:
5024:
5023:
5020:
5019:
5017:
5016:
5010:
5008:
5004:
5003:
5001:
5000:
4995:
4990:
4985:
4980:
4975:
4970:
4965:
4960:
4955:
4950:
4944:
4942:
4936:
4935:
4933:
4932:
4926:
4920:
4913:
4911:
4909:Bicycloalkanes
4905:
4904:
4902:
4901:
4899:
4894:
4889:
4884:
4879:
4873:
4871:
4865:
4864:
4862:
4861:
4856:
4851:
4846:
4841:
4836:
4831:
4826:
4820:
4818:
4812:
4811:
4808:
4807:
4805:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4764:
4758:
4756:
4752:
4751:
4749:
4748:
4743:
4738:
4733:
4728:
4723:
4718:
4713:
4708:
4703:
4697:
4695:
4694:Linear alkanes
4688:
4681:
4675:
4664:
4656:
4655:
4648:
4647:
4640:
4633:
4625:
4619:
4618:
4602:
4594:
4588:
4582:
4576:
4568:
4567:External links
4565:
4563:
4562:
4547:
4521:
4489:
4453:
4428:
4403:
4387:
4376:Proposition 65
4368:
4334:
4315:
4285:
4268:
4241:Acad Emerg Med
4227:
4199:
4148:
4119:
4095:
4086:
4068:
4023:
4005:
3978:
3971:978-3527306732
3970:
3939:
3912:(3): 197â200.
3892:
3845:
3818:
3775:
3763:
3736:
3734: : 20â28.
3715:
3704:(3): 327â359.
3682:
3647:
3620:(6): 272â290.
3614:J Appl Toxicol
3604:
3582:
3558:
3549:
3522:
3515:
3488:
3459:
3430:
3408:
3376:
3346:
3339:
3284:
3255:
3234:
3205:
3195:
3193:
3190:
3189:
3188:
3182:
3173:
3168:
3163:
3150:
3143:
3140:
3137:
3136:
3130:
3129:
3126:
3123:
3120:
3117:
3114:
3111:
3107:
3104:
3100:
3099:
3096:
3093:
3090:
3087:
3084:
3080:
3076:
3073:
3067:
3066:
3063:
3060:
3057:
3054:
3051:
3047:
3043:
3040:
3034:
3033:
3030:
3027:
3024:
3021:
3018:
3014:
3010:
3007:
3001:
3000:
2997:
2994:
2991:
2988:
2985:
2981:
2977:
2974:
2968:
2967:
2964:
2961:
2958:
2955:
2952:
2949:
2945:
2941:
2938:
2934:
2933:
2931:
2929:
2926:
2923:
2920:
2916:
2912:
2909:
2905:
2904:
2901:
2898:
2895:
2892:
2889:
2885:
2881:
2878:
2872:
2871:
2868:
2865:
2858:
2855:
2852:
2848:
2844:
2841:
2837:
2836:
2833:
2831:
2829:
2826:
2823:
2820:
2816:
2812:
2809:
2803:
2802:
2799:
2797:
2794:
2791:
2788:
2785:
2781:
2777:
2774:
2768:
2767:
2762:
2759:
2758:Boiling point
2756:
2755:Melting point
2753:
2750:
2747:
2737:
2734:
2684:
2681:
2677:Proposition 65
2623:carcinogenesis
2560:Main article:
2557:
2556:Health effects
2554:
2541:
2538:
2466:
2463:
2381:
2378:
2372:, and to make
2357:
2354:
2336:
2314:
2311:
2270:
2267:
2251:
2248:
2237:Muscodor albus
2196:
2193:
2173:Eastern Europe
2142:benzothiophene
2085:
2082:
2066:
2065:
2061:
2057:
2053:
2049:
2045:
2041:
2037:
2033:
2010:
1995:
1986:
1966:
1957:
1935:
1928:
1920:
1917:
1909:
1908:
1904:
1900:
1896:
1892:
1876:
1873:
1869:
1868:
1863:
1859:
1855:
1851:
1847:
1843:
1839:
1835:
1811:regiochemistry
1759:
1756:
1754:
1751:
1726:
1711:
1689:
1686:
1680:
1650:
1649:
1621:
1620:
1575:
1572:
1543:
1540:
1499:
1496:
1464:
1453:
1434:
1431:
1430:
1425:
1403:
1402:
1398:standard state
1395:
1392:
1391:
1388:
1382:
1379:
1378:
1375:
1369:
1366:
1365:
1362:
1356:
1353:
1352:
1343:
1342:
1333:
1324:
1322:
1319:
1318:
1311:
1310:
1307:
1301:
1298:
1297:
1294:
1288:
1287:
1284:
1277:
1274:
1273:
1270:
1264:
1263:
1253:
1246:
1239:
1224:
1223:
1222:
1221:
1219:
1210:
1209:
1192:
1187:
1184:
1183:
1166:
1161:
1158:
1157:
1152:
1147:
1144:
1143:
1121:
1116:
1113:
1112:
1102:
1101:
1097:mixtures with
1080:
1077:
1074:
1073:
1064:
1063:
1059:
1058:
1055:
1049:
1043:
1035:
1032:
1031:
1028:
1019:
1013:
1010:
1009:
1006:
1000:
994:
986:
983:
982:
979:
973:
962:
959:
958:
955:
943:
940:
939:
935:
934:
931:
917:
915:
910:
907:
906:
901:
895:
890:
887:
886:
882:
879:
874:
871:
870:
865:
860:
857:
856:
852:
851:
844:
838:
837:
834:
829:
821:
818:
817:
806:
800:
799:
796:
790:
787:
786:
783:
778:
768:
765:
764:
755:
753:Vapor pressure
749:
748:
745:
736:
735:
728:
718:
717:
708:
698:
697:
688:
678:
677:
668:
658:
657:
648:
638:
637:
625:
618:
611:
604:
600:
583:
577:
576:
565:
560:
557:
556:
551:
545:
544:
537:
531:
530:
523:
517:
516:
513:
507:
506:
503:
499:
498:
492:
486:
485:
482:
476:
471:
466:
463:
462:
458:
457:
455:
454:
452:c1c2ccccc2ccc1
451:
443:
442:
441:
438:
437:
435:
434:
430:
427:
426:
424:
420:
417:
416:
408:
407:
406:
403:
402:
400:
399:
386:
384:
372:
369:
368:
366:
365:
357:
355:
349:
348:
346:
345:
341:
339:
333:
332:
330:
329:
321:
319:
311:
308:
307:
305:
304:
296:
294:
288:
287:
284:
279:
276:
275:
273:
272:
268:
266:
258:
257:
247:
239:
238:
236:
235:
227:
225:
219:
218:
216:
215:
207:
205:
199:
198:
196:
195:
187:
185:
179:
178:
175:
170:
167:
166:
164:
163:
155:
153:
146:
143:
142:
140:
139:
131:
129:
124:
121:
120:
116:
115:
112:
108:
107:
104:
98:
97:
93:
92:
84:
83:
75:
74:
71:
70:
60:
9:
6:
4:
3:
2:
8065:
8054:
8051:
8049:
8046:
8044:
8041:
8039:
8036:
8034:
8031:
8029:
8026:
8025:
8023:
8008:
7998:
7996:
7986:
7984:
7974:
7972:
7971:
7962:
7961:
7958:
7952:
7949:
7947:
7944:
7942:
7939:
7936:
7933:
7931:
7928:
7926:
7923:
7921:
7918:
7916:
7913:
7911:
7908:
7906:
7903:
7901:
7898:
7896:
7893:
7891:
7888:
7886:
7883:
7881:
7878:
7876:
7873:
7871:
7870:Homochirality
7868:
7866:
7863:
7861:
7858:
7856:
7853:
7851:
7848:
7846:
7843:
7841:
7838:
7836:
7833:
7831:
7828:
7826:
7823:
7821:
7818:
7816:
7813:
7811:
7808:
7806:
7803:
7801:
7798:
7796:
7793:
7792:
7790:
7788:
7784:
7778:
7775:
7773:
7770:
7768:
7765:
7763:
7760:
7758:
7752:
7750:
7743:
7741:
7738:
7736:
7733:
7731:
7728:
7726:
7725:Methoxyethane
7723:
7721:
7718:
7716:
7713:
7712:
7710:
7708:
7704:
7698:
7695:
7693:
7686:
7684:
7681:
7679:
7676:
7674:
7671:
7669:
7666:
7664:
7661:
7659:
7656:
7654:
7651:
7648:
7645:
7643:
7640:
7639:
7637:
7633:
7629:
7619:
7616:
7614:
7611:
7609:
7608:Butyronitrile
7606:
7604:
7601:
7599:
7596:
7594:
7591:
7589:
7586:
7584:
7583:Ethyl formate
7581:
7579:
7576:
7574:
7571:
7569:
7562:
7551:
7548:
7546:
7543:
7541:
7538:
7536:
7533:
7532:
7530:
7528:
7520:
7514:
7511:
7509:
7508:Propionitrile
7506:
7504:
7501:
7499:
7496:
7494:
7491:
7489:
7486:
7484:
7481:
7479:
7476:
7474:
7471:
7469:
7466:
7465:
7463:
7461:
7455:
7449:
7446:
7444:
7441:
7439:
7436:
7434:
7431:
7429:
7426:
7424:
7421:
7419:
7416:
7414:
7411:
7409:
7406:
7405:
7403:
7401:
7395:
7389:
7388:Vinyl alcohol
7386:
7384:
7381:
7379:
7376:
7374:
7371:
7369:
7366:
7364:
7361:
7359:
7356:
7354:
7351:
7347:
7346:Vinyl cyanide
7344:
7343:
7342:
7341:Acrylonitrile
7339:
7337:
7334:
7333:
7331:
7329:
7323:
7317:
7314:
7312:
7309:
7307:
7306:Pentynylidyne
7304:
7302:
7299:
7297:
7294:
7292:
7289:
7287:
7284:
7282:
7275:
7273:
7270:
7268:
7265:
7263:
7260:
7258:
7255:
7253:
7250:
7248:
7245:
7243:
7240:
7239:
7237:
7235:
7229:
7223:
7220:
7218:
7215:
7213:
7210:
7208:
7205:
7203:
7202:Methylenimine
7200:
7198:
7195:
7193:
7190:
7188:
7185:
7183:
7180:
7178:
7175:
7173:
7170:
7168:
7165:
7163:
7160:
7158:
7155:
7153:
7150:
7148:
7145:
7143:
7140:
7137:
7134:
7133:
7131:
7129:
7123:
7117:
7114:
7112:
7109:
7107:
7104:
7102:
7099:
7097:
7094:
7092:
7089:
7087:
7084:
7082:
7081:Propynylidyne
7079:
7077:
7074:
7072:
7071:Methyl cation
7069:
7067:
7064:
7062:
7059:
7057:
7054:
7052:
7049:
7047:
7044:
7042:
7039:
7037:
7034:
7032:
7031:Fulminic acid
7029:
7027:
7024:
7022:
7019:
7017:
7014:
7012:
7009:
7007:
7004:
7003:
7001:
6999:
6993:
6987:
6984:
6982:
6979:
6977:
6974:
6972:
6969:
6967:
6964:
6962:
6959:
6957:
6954:
6952:
6949:
6947:
6944:
6942:
6939:
6937:
6934:
6932:
6929:
6927:
6924:
6922:
6919:
6917:
6914:
6912:
6909:
6907:
6906:Nitrous oxide
6904:
6902:
6895:
6893:
6890:
6888:
6885:
6883:
6880:
6878:
6875:
6873:
6870:
6868:
6865:
6863:
6860:
6857:
6854:
6851:
6848:
6846:
6843:
6841:
6838:
6836:
6833:
6831:
6828:
6826:
6823:
6821:
6818:
6816:
6813:
6811:
6808:
6806:
6803:
6801:
6800:Amino radical
6798:
6796:
6793:
6791:
6788:
6787:
6785:
6783:
6779:
6774:
6765:
6756:
6746:
6743:
6741:
6738:
6736:
6733:
6731:
6730:Sodium iodide
6728:
6726:
6723:
6721:
6718:
6716:
6713:
6711:
6708:
6706:
6703:
6701:
6698:
6696:
6693:
6690:
6687:
6685:
6682:
6680:
6677:
6674:
6671:
6669:
6666:
6664:
6661:
6659:
6656:
6654:
6651:
6649:
6646:
6643:
6640:
6638:
6635:
6633:
6630:
6628:
6625:
6623:
6620:
6618:
6615:
6613:
6612:Cyano radical
6610:
6608:
6605:
6603:
6600:
6598:
6595:
6593:
6592:Carbon cation
6590:
6588:
6585:
6583:
6580:
6578:
6575:
6573:
6570:
6569:
6567:
6565:
6561:
6558:
6556:
6552:
6548:
6541:
6536:
6534:
6529:
6527:
6522:
6521:
6518:
6506:
6503:
6501:
6498:
6496:
6493:
6491:
6488:
6486:
6483:
6482:
6480:
6476:
6470:
6467:
6465:
6462:
6460:
6457:
6455:
6452:
6450:
6447:
6445:
6442:
6440:
6437:
6435:
6432:
6429:
6425:
6422:
6420:
6417:
6415:
6412:
6410:
6407:
6405:
6402:
6401:
6399:
6395:
6389:
6386:
6384:
6381:
6379:
6376:
6374:
6371:
6369:
6366:
6364:
6363:Benzoperylene
6361:
6359:
6356:
6355:
6353:
6349:
6343:
6340:
6338:
6335:
6333:
6330:
6328:
6325:
6323:
6320:
6318:
6315:
6313:
6310:
6308:
6305:
6303:
6300:
6298:
6295:
6293:
6290:
6286:
6284:
6279:
6277:
6274:
6272:
6269:
6268:
6267:
6264:
6262:
6259:
6258:
6256:
6252:
6246:
6243:
6241:
6238:
6236:
6233:
6231:
6228:
6226:
6223:
6221:
6218:
6216:
6213:
6211:
6210:Benzofluorene
6208:
6206:
6205:Benzofluorene
6203:
6201:
6198:
6197:
6195:
6191:
6185:
6182:
6180:
6177:
6175:
6172:
6170:
6167:
6165:
6162:
6160:
6157:
6156:
6154:
6150:
6144:
6141:
6139:
6136:
6134:
6131:
6130:
6128:
6124:
6120:
6113:
6108:
6106:
6101:
6099:
6094:
6093:
6090:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6059:
6057:
6053:
6043:
6041:
6037:
6035:
6032:
6030:
6027:
6025:
6022:
6021:
6019:
6015:
6009:
6006:
6004:
6001:
5999:
5996:
5995:
5993:
5991:Vinylbenzenes
5989:
5979:
5976:
5974:
5971:
5969:
5966:
5964:
5961:
5960:
5958:
5954:
5944:
5941:
5939:
5938:-Butylbenzene
5937:
5933:
5931:
5930:-Butylbenzene
5929:
5925:
5923:
5922:-Butylbenzene
5921:
5917:
5916:
5914:
5910:
5904:
5901:
5899:
5896:
5894:
5891:
5890:
5888:
5886:
5882:
5876:
5874:
5870:
5868:
5866:
5862:
5860:
5858:
5854:
5853:
5851:
5849:
5845:
5842:
5840:
5836:
5826:
5823:
5821:
5819:
5815:
5813:
5810:
5809:
5807:
5803:
5797:
5794:
5792:
5789:
5787:
5784:
5783:
5781:
5779:
5775:
5772:
5770:
5766:
5756:
5753:
5752:
5750:
5746:
5740:
5738:
5734:
5732:
5730:
5726:
5724:
5722:
5718:
5717:
5715:
5713:
5709:
5706:
5704:
5700:
5694:
5691:
5690:
5688:
5686:
5685:Alkylbenzenes
5682:
5672:
5669:
5667:
5664:
5662:
5659:
5657:
5654:
5652:
5649:
5647:
5644:
5642:
5639:
5637:
5634:
5632:
5629:
5627:
5624:
5623:
5621:
5617:
5611:
5608:
5606:
5603:
5601:
5598:
5596:
5593:
5591:
5588:
5586:
5583:
5582:
5580:
5578:
5574:
5571:
5569:
5565:
5562:
5560:
5554:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5515:
5513:
5509:
5503:
5500:
5498:
5495:
5493:
5490:
5488:
5485:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5464:
5462:
5460:
5456:
5450:
5447:
5445:
5442:
5440:
5437:
5435:
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5412:
5411:
5409:
5407:
5403:
5397:
5394:
5393:
5391:
5389:
5385:
5379:
5377:
5374:
5372:
5369:
5367:
5364:
5362:
5359:
5357:
5354:
5353:
5351:
5349:
5345:
5339:
5336:
5334:
5331:
5329:
5326:
5324:
5321:
5319:
5316:
5314:
5311:
5309:
5306:
5304:
5301:
5300:
5298:
5296:
5292:
5282:
5279:
5277:
5274:
5272:
5269:
5267:
5264:
5262:
5259:
5257:
5254:
5253:
5251:
5247:
5241:
5238:
5236:
5233:
5231:
5228:
5226:
5223:
5221:
5218:
5216:
5213:
5211:
5208:
5206:
5203:
5201:
5198:
5197:
5195:
5191:
5188:
5184:
5177:
5171:
5167:
5157:
5154:
5152:
5149:
5147:
5144:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5123:
5121:
5117:
5111:
5108:
5106:
5103:
5101:
5098:
5096:
5093:
5091:
5088:
5086:
5083:
5081:
5078:
5076:
5073:
5071:
5068:
5067:
5065:
5061:
5058:
5055:
5048:
5042:
5038:
5035:
5029:
5025:
5015:
5012:
5011:
5009:
5005:
4999:
4996:
4994:
4991:
4989:
4986:
4984:
4981:
4979:
4978:Dodecahedrane
4976:
4974:
4971:
4969:
4966:
4964:
4961:
4959:
4956:
4954:
4951:
4949:
4946:
4945:
4943:
4941:
4937:
4930:
4927:
4924:
4921:
4918:
4915:
4914:
4912:
4910:
4906:
4900:
4898:
4895:
4893:
4890:
4888:
4885:
4883:
4880:
4878:
4875:
4874:
4872:
4870:
4866:
4860:
4857:
4855:
4852:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4821:
4819:
4817:
4813:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4759:
4757:
4753:
4747:
4744:
4742:
4739:
4737:
4734:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4714:
4712:
4709:
4707:
4704:
4702:
4699:
4698:
4696:
4692:
4689:
4685:
4678:
4672:
4668:
4665:
4657:
4653:
4646:
4641:
4639:
4634:
4632:
4627:
4626:
4623:
4615:
4614:
4608:
4603:
4600:
4599:
4595:
4592:
4589:
4586:
4583:
4580:
4577:
4574:
4571:
4570:
4559:
4551:
4536:
4532:
4525:
4510:
4506:
4505:The Telegraph
4501:
4493:
4474:
4470:
4463:
4462:"Naphthalene"
4457:
4442:
4438:
4432:
4417:
4413:
4407:
4400:
4396:
4391:
4384:
4380:
4377:
4372:
4364:
4352:
4337:
4331:
4327:
4326:
4319:
4303:
4299:
4295:
4289:
4283:
4279:
4278:
4272:
4264:
4260:
4255:
4250:
4246:
4242:
4238:
4231:
4215:
4214:
4209:
4203:
4194:
4189:
4184:
4179:
4175:
4171:
4167:
4163:
4159:
4152:
4144:
4140:
4136:
4132:
4131:
4123:
4115:
4111:
4107:
4103:
4102:
4090:
4082:
4078:
4072:
4064:
4060:
4055:
4050:
4046:
4042:
4038:
4036:
4027:
4019:
4015:
4009:
4001:
3997:
3993:
3989:
3982:
3973:
3967:
3963:
3962:
3954:
3952:
3950:
3948:
3946:
3944:
3935:
3931:
3927:
3923:
3919:
3915:
3911:
3907:
3903:
3896:
3888:
3884:
3880:
3876:
3872:
3868:
3864:
3860:
3856:
3849:
3841:
3837:
3833:
3829:
3822:
3814:
3810:
3806:
3802:
3798:
3794:
3790:
3786:
3779:
3772:
3767:
3760:
3753:
3746:
3740:
3733:
3729:
3725:
3719:
3711:
3707:
3703:
3699:
3698:
3693:
3686:
3678:
3674:
3670:
3666:
3662:
3658:
3651:
3643:
3639:
3635:
3631:
3627:
3623:
3619:
3615:
3608:
3600:
3596:
3592:
3591:"Naphthalene"
3586:
3578:
3574:
3567:
3565:
3563:
3553:
3546:
3542:
3537:
3535:
3533:
3531:
3529:
3527:
3518:
3512:
3508:
3507:
3499:
3497:
3495:
3493:
3478:on 2016-03-04
3477:
3473:
3469:
3463:
3449:on 2016-03-04
3448:
3444:
3440:
3434:
3427:
3425:
3420:
3415:
3413:
3404:
3400:
3399:
3391:
3389:
3387:
3385:
3383:
3381:
3366:
3362:
3361:"naphthalene"
3355:
3353:
3351:
3342:
3336:
3332:
3328:
3324:
3323:
3315:
3313:
3311:
3309:
3307:
3305:
3303:
3301:
3299:
3297:
3295:
3293:
3291:
3289:
3270:
3264:
3262:
3260:
3251:
3245:
3237:
3231:
3227:
3223:
3219:
3215:
3209:
3200:
3196:
3186:
3183:
3181:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3158:
3154:
3151:
3149:
3146:
3145:
3135:
3132:
3131:
3127:
3124:
3121:
3118:
3115:
3105:
3102:
3101:
3097:
3094:
3091:
3088:
3085:
3074:
3072:
3069:
3068:
3064:
3061:
3058:
3055:
3052:
3041:
3039:
3036:
3035:
3031:
3028:
3025:
3022:
3019:
3008:
3006:
3003:
3002:
2998:
2995:
2992:
2989:
2986:
2975:
2973:
2970:
2969:
2965:
2962:
2959:
2956:
2953:
2939:
2936:
2935:
2932:
2930:
2928:160 (15 Torr)
2927:
2924:
2921:
2910:
2907:
2906:
2902:
2899:
2896:
2893:
2890:
2879:
2877:
2874:
2873:
2869:
2866:
2863:
2859:
2856:
2853:
2842:
2839:
2838:
2834:
2832:
2830:
2827:
2824:
2810:
2808:
2805:
2804:
2800:
2798:
2795:
2792:
2789:
2775:
2773:
2770:
2769:
2766:
2763:
2760:
2757:
2754:
2751:
2748:
2745:
2744:
2741:
2733:
2731:
2727:
2722:
2720:
2715:
2713:
2709:
2705:
2701:
2697:
2693:
2689:
2688:US government
2680:
2678:
2674:
2670:
2666:
2662:
2658:
2654:
2649:
2647:
2643:
2640:
2636:
2632:
2631:neuroblastoma
2628:
2624:
2620:
2615:
2613:
2609:
2605:
2601:
2597:
2593:
2589:
2585:
2581:
2577:
2573:
2569:
2563:
2553:
2551:
2547:
2537:
2535:
2531:
2527:
2523:
2518:
2516:
2512:
2508:
2506:
2502:
2498:
2493:
2491:
2490:agrichemicals
2487:
2479:
2475:
2471:
2462:
2460:
2456:
2452:
2448:
2444:
2440:
2435:
2433:
2429:
2424:
2422:
2418:
2413:
2411:
2407:
2403:
2399:
2395:
2391:
2387:
2377:
2375:
2371:
2367:
2363:
2353:
2351:
2347:
2343:
2339:
2332:
2328:
2324:
2320:
2310:
2308:
2304:
2300:
2296:
2292:
2288:
2284:
2280:
2276:
2266:
2264:
2262:
2257:
2247:
2245:
2244:
2239:
2238:
2233:
2229:
2225:
2221:
2217:
2213:
2208:
2206:
2202:
2192:
2190:
2186:
2182:
2178:
2174:
2170:
2166:
2165:North America
2161:
2159:
2155:
2151:
2147:
2143:
2139:
2135:
2131:
2127:
2123:
2119:
2115:
2109:
2107:
2103:
2099:
2090:
2081:
2079:
2075:
2071:
2031:
2030:
2029:
2027:
2023:
2019:
2002:
1979:
1975:
1950:
1946:
1941:
1926:
1916:
1915:derivatives.
1914:
1890:
1889:
1888:
1886:
1882:
1881:phenyllithium
1872:
1832:
1831:
1830:
1828:
1824:
1820:
1816:
1812:
1807:
1805:
1801:
1797:
1793:
1789:
1785:
1781:
1777:
1773:
1769:
1765:
1764:electrophilic
1750:
1748:
1744:
1740:
1736:
1732:
1725:
1721:
1717:
1710:
1706:
1702:
1699:
1695:
1685:
1683:
1675:
1673:
1669:
1665:
1657:
1653:
1647:
1643:
1642:
1641:
1639:
1635:
1631:
1626:
1618:
1614:
1613:
1612:
1610:
1606:
1602:
1598:
1594:
1590:
1586:
1582:
1571:
1568:
1563:
1561:
1557:
1553:
1549:
1539:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1509:
1505:
1495:
1493:
1489:
1485:
1481:
1477:
1473:
1460:
1449:
1445:with formula
1444:
1440:
1428:
1421:
1416:
1399:
1393:
1389:
1385:
1381:
1380:
1376:
1373:(Recommended)
1372:
1368:
1367:
1363:
1360:(Permissible)
1359:
1355:
1354:
1350:
1349:
1344:
1334:
1330:
1321:
1320:
1316:
1312:
1308:
1304:
1300:
1299:
1295:
1293:
1290:
1289:
1285:
1282:
1276:
1275:
1271:
1269:
1266:
1265:
1258:
1251:
1244:
1220:
1217:
1216:
1212:
1211:
1193:
1190:
1186:
1185:
1167:
1164:
1160:
1159:
1156:
1153:
1150:
1146:
1145:
1141:
1136:
1131:
1126:
1122:
1119:
1115:
1114:
1110:
1108:
1103:
1100:
1096:
1092:
1088:
1084:
1081:
1076:
1075:
1071:
1070:
1065:
1060:
1056:
1048:
1040:
1034:
1033:
1029:
1024:
1016:
1012:
1011:
1008:78.53 kJ/mol
1007:
999:
991:
985:
984:
980:
972:
967:
961:
960:
956:
951:
946:
945:Heat capacity
942:
941:
936:
928:
924:
920:
916:
913:
909:
908:
896:
893:
889:
888:
880:
877:
873:
872:
869:
866:
863:
859:
858:
853:
845:
843:
840:
839:
835:
828:
824:
820:
819:
807:
805:
802:
801:
797:
793:
789:
788:
784:
777:
773:
767:
766:
756:
754:
751:
750:
746:
744:
743:
738:
737:
729:
727:
723:
720:
719:
709:
707:
703:
700:
699:
689:
687:
683:
680:
679:
669:
667:
663:
660:
659:
649:
647:
643:
640:
639:
636:
632:
628:
621:
614:
607:
596:
592:
588:
584:
582:
579:
578:
566:
563:
559:
558:
552:
550:
549:Boiling point
547:
546:
538:
536:
535:Melting point
533:
532:
524:
522:
519:
518:
514:
512:
509:
508:
504:
501:
500:
493:
491:
488:
487:
472:
469:
465:
464:
459:
450:
449:
446:
439:
425:
415:
414:
411:
404:
396:
392:
391:DTXSID8020913
388:
387:
385:
375:
371:
370:
363:
359:
358:
356:
354:
351:
350:
343:
342:
340:
338:
335:
334:
327:
323:
322:
320:
314:
310:
309:
302:
298:
297:
295:
293:
290:
289:
285:
282:
278:
277:
270:
269:
267:
265:
260:
259:
255:
251:
248:
246:
244:ECHA InfoCard
241:
240:
233:
229:
228:
226:
224:
221:
220:
213:
209:
208:
206:
204:
201:
200:
193:
189:
188:
186:
184:
181:
180:
176:
173:
169:
168:
161:
157:
156:
154:
150:
145:
144:
137:
133:
132:
130:
127:
123:
122:
117:
109:
103:
99:
94:
90:
85:
81:
76:
65:
61:
55:
51:
50:
46:
38:
34:
30:
19:
8048:Insecticides
8028:Naphthalenes
7963:
7946:Spectroscopy
7800:Astrobiology
7761:
7653:Formaldehyde
7545:Benzonitrile
7336:Acetaldehyde
7291:Methanethiol
7242:Acetonitrile
7147:Carbodiimide
7026:Formaldehyde
7021:Cyanoethynyl
6872:Iron cyanide
6867:Hydroperoxyl
6668:Nitric oxide
6409:Dicoronylene
6358:Anthanthrene
6282:
6240:Triphenylene
6225:Fluoranthene
6184:Phenanthrene
6159:Acenaphthene
6142:
6039:
5935:
5927:
5919:
5872:
5864:
5856:
5817:
5791:Pseudocumene
5755:Ethylbenzene
5736:
5728:
5720:
5651:Phenanthrene
5584:
5559:hydrocarbons
5434:Cycloheptyne
5424:Cyclopentyne
5414:Cyclopropyne
5406:Cycloalkynes
5323:Cycloheptene
5313:Cyclopentene
5303:Cyclopropene
5295:Cycloalkenes
5182:
5175:
5053:
5046:
5033:hydrocarbons
5014:Spiroalkanes
4844:Cycloheptane
4834:Cyclopentane
4824:Cyclopropane
4816:Cycloalkanes
4683:
4676:
4663:hydrocarbons
4652:Hydrocarbons
4611:
4596:
4555:
4550:
4539:. Retrieved
4534:
4524:
4513:. Retrieved
4504:
4492:
4480:. Retrieved
4468:
4456:
4444:. Retrieved
4440:
4431:
4419:. Retrieved
4415:
4406:
4398:
4390:
4371:
4341:December 25,
4339:. Retrieved
4324:
4318:
4306:. Retrieved
4302:the original
4297:
4288:
4275:
4271:
4244:
4240:
4230:
4220:December 11,
4218:. Retrieved
4211:
4202:
4165:
4161:
4151:
4134:
4128:
4122:
4105:
4099:
4089:
4081:the original
4071:
4044:
4041:Microbiology
4040:
4034:
4026:
4017:
4008:
3991:
3987:
3981:
3959:
3909:
3905:
3895:
3862:
3858:
3848:
3831:
3828:J. Org. Chem
3827:
3821:
3788:
3784:
3778:
3770:
3766:
3758:
3739:
3731:
3727:
3718:
3701:
3695:
3685:
3660:
3656:
3650:
3617:
3613:
3607:
3594:
3585:
3552:
3505:
3480:. Retrieved
3476:the original
3471:
3462:
3451:. Retrieved
3447:the original
3442:
3433:
3422:
3397:
3368:. Retrieved
3365:chemister.ru
3364:
3320:
3276:. Retrieved
3213:
3208:
3199:
2739:
2723:
2721:since 2008.
2716:
2686:
2650:
2616:
2565:
2543:
2526:beta blocker
2519:
2509:
2494:
2483:
2478:beta blocker
2451:formaldehyde
2436:
2425:
2414:
2383:
2366:plasticizers
2359:
2327:nitrobenzene
2323:benzonitrile
2316:
2272:
2260:
2253:
2241:
2235:
2209:
2198:
2162:
2114:distillation
2110:
2095:
2078:permanganate
2067:
2003:
1945:hydrogenated
1942:
1922:
1910:
1878:
1870:
1809:In terms of
1808:
1761:
1746:
1742:
1734:
1730:
1723:
1719:
1715:
1708:
1704:
1696:of about 10
1691:
1678:
1676:
1662:
1651:
1633:
1629:
1622:
1611:structures.
1605:ground state
1585:valence bond
1577:
1564:
1555:
1554:, rings are
1545:
1515:
1504:distillation
1501:
1438:
1437:
1347:
1314:
1279:Autoignition
1214:
1154:
1106:
1078:Main hazards
1067:
1046:
1022:
997:
970:
949:
926:
922:
918:
826:
775:
741:
726:butyric acid
555:at 760 mmHg
543:at 760 mmHg
337:RTECS number
119:Identifiers
111:Other names
43:Naphthalene
8033:Antiseptics
7920:Outer space
7830:Cosmic dust
7795:Abiogenesis
7707:Unconfirmed
7663:Heavy water
7503:Ethanethiol
7418:Cyanoallene
7408:Acetic acid
7378:Methylamine
7262:Diacetylene
7177:Formic acid
7167:Cyanomethyl
6825:Diazenylium
6815:CCP radical
6691:(molecular)
6675:(molecular)
6644:(molecular)
6383:Triangulene
6368:Corannulene
6276:Benzopyrene
6271:Benzopyrene
6266:Benzopyrene
6143:Naphthalene
5839:C4-Benzenes
5796:Hemellitene
5769:C3-Benzenes
5703:C2-Benzenes
5666:Corannulene
5585:Naphthalene
5449:Cyclodecyne
5444:Cyclononyne
5439:Cyclooctyne
5429:Cyclohexyne
5419:Cyclobutyne
5338:Cyclodecene
5333:Cyclononene
5328:Cyclooctene
5318:Cyclohexene
5308:Cyclobutene
5028:Unsaturated
4859:Cyclodecane
4854:Cyclononane
4849:Cyclooctane
4839:Cyclohexane
4829:Cyclobutane
4598:Naphthalene
4591:Naphthalene
4579:Naphthalene
4573:Naphthalene
4399:Physorg.com
4359:|work=
4247:(1): 42â7.
4193:1885/229663
4130:Tetrahedron
3663:: 209â221.
3545:Naphthalene
3419:Naphthalene
2752:Molar mass
2663:in humans,
2639:bronchiolar
2550:sublimation
2522:propranolol
2474:Propranolol
2432:surfactants
2374:alkyd resin
2346:DielsâAlder
2092:Naphthalene
1827:Sulfonation
1815:Sulfonation
1806:catalysts.
1694:resistivity
1550:rings. (In
1516:naphthaline
1510:. In 1821,
1480:ppm by mass
1439:Naphthalene
1329:median dose
1315:Lethal dose
1281:temperature
1268:Flash point
1149:Signal word
1089:, possible
1072:(OHS/OSH):
892:Point group
876:Space group
770:Henry's law
666:acetic acid
585:Soluble in
502:Appearance
461:Properties
250:100.001.863
212:ChEMBL16293
192:CHEBI:16482
105:Naphthalene
18:Naphthaline
8022:Categories
7835:Cosmic ray
7777:Silylidyne
7740:Hemolithin
7715:Anthracene
7632:Deuterated
7613:Pyrimidine
7423:Ethanimine
7286:Ketenimine
7142:Butadiynyl
6966:Thioformyl
6820:Chloronium
6428:Hexa-cata-
6169:Anthracene
5898:Prehnitene
5786:Mesitylene
5641:Circulenes
5590:Anthracene
5518:Alkatriene
5487:Heptadiene
5477:Pentadiene
5467:Propadiene
5396:Norbornene
5266:Isoheptyne
5256:Isopentyne
5141:Isoheptene
5131:Isopentene
4953:Diamondoid
4948:Adamantane
4923:Norbornane
4787:Isoheptane
4777:Neopentane
4767:Isopentane
4541:2012-11-23
4515:2013-11-23
3482:2014-06-21
3472:DDBST GmbH
3453:2014-06-21
3443:DDBST GmbH
3370:2014-06-21
3278:2014-06-21
3192:References
3180:2-Naphthol
3176:1-Naphthol
2876:1-Naphthol
2706:has set a
2698:has set a
2683:Regulation
2540:Other uses
2530:nabumetone
2511:Alkylation
2398:pesticides
2394:2-naphthol
2390:1-naphthol
2342:anthracene
2232:endophytic
2189:Kazakhstan
2177:metallurgy
2124:to remove
2084:Production
2080:reagents.
2056:O + 2 CO
1875:Lithiation
1729:(멉
m) and
1722:)), where
1601:conjugated
1536:Carl GrÀbe
1118:Pictograms
1091:carcinogen
1087:sensitizer
1039:combustion
868:Monoclinic
855:Structure
722:Solubility
702:Solubility
686:chloroform
682:Solubility
662:Solubility
642:Solubility
581:Solubility
490:Molar mass
362:2166IN72UN
223:ChemSpider
147:3D model (
126:CAS Number
102:IUPAC name
7767:Phosphine
7635:molecules
7568:fullerene
7468:Acetamide
7272:Formamide
7152:Cyanamide
7006:Acetylene
6981:Tricarbon
6892:Methylene
6877:Isoformyl
6782:Triatomic
6555:Molecules
6505:Phenacene
6495:Cyclacene
6490:Circulene
6419:Heptacene
6327:Pentacene
6235:Tetracene
6179:Phenalene
6067:Annulynes
6062:Annulenes
5903:Isodurene
5636:Helicenes
5610:Heptacene
5600:Pentacene
5595:Tetracene
5523:Alkadiyne
5502:Decadiene
5497:Nonadiene
5492:Octadiene
5482:Hexadiene
5472:Butadiene
5281:Isodecyne
5276:Isononyne
5271:Isooctyne
5261:Isohexyne
5156:Isodecene
5151:Isononene
5146:Isooctene
5136:Isohexene
5126:Isobutene
5031:aliphatic
4988:Churchane
4983:Basketane
4802:Isodecane
4797:Isononane
4792:Isooctane
4782:Isohexane
4762:Isobutane
4661:aliphatic
4659:Saturated
4361:ignored (
4351:cite book
3934:0031-9007
3887:0021-9606
3771:Blue Book
3331:CRC Press
3244:cite book
3171:Mothballs
2661:cataracts
2584:confusion
2295:pesticide
2279:mothballs
2212:magnolias
2102:petroleum
2070:Oxidation
1949:catalysts
1907:Li + BuBr
1784:alkylated
1766:aromatic
1609:resonance
1512:John Kidd
1492:mothballs
1109:labelling
1095:explosive
1083:Flammable
990:formation
964:Std molar
842:Viscosity
589:, liquid
344:QJ0525000
271:214-552-7
263:EC Number
33:naphthene
7754:Linear C
7735:Graphene
7647:Ammonium
7448:Acrolein
7311:Propynal
7296:Methanol
7267:Ethylene
7136:Ammonium
6911:Nitroxyl
6735:Sulfanyl
6679:Imidogen
6673:Nitrogen
6642:Hydrogen
6587:Argonium
6564:Diatomic
6500:Helicene
6454:Sumanene
6444:Rubicene
6434:Kekulene
6404:Coronene
6397:7+ rings
6388:Zethrene
6378:Hexacene
6332:Perylene
6220:Chrysene
6174:Fluorene
6133:Butalene
5671:Kekulene
5656:Chrysene
5646:Butalene
5631:Fluorene
5605:Hexacene
5557:Aromatic
5528:Cumulene
4998:Twistane
4993:Pagodane
4973:Prismane
4509:Archived
4473:Archived
4379:Archived
4308:March 6,
4263:10894241
4063:12427963
4018:Sci/Tech
3813:96765335
3752:Archived
3677:97798085
3642:36525625
3601:(NIOSH).
3579:(NIOSH).
3157:Tetralin
3142:See also
2860:190 (35
2761:Density
2657:Group 2B
2642:adenomas
2635:alveolar
2608:jaundice
2596:diarrhea
2592:vomiting
2505:solvents
2497:tetralin
2486:azo dyes
2447:concrete
2439:polymers
2307:opossums
2291:fumigant
2275:fumigant
2269:Fumigant
2228:nematode
2205:creosote
2201:homologs
2148:(0.2%),
2098:coal tar
2074:chromate
2040:+ 4.5 O
2022:catalyst
1974:tetralin
1800:sulfuric
1798:, using
1796:alcohols
1774:to give
1772:catalyst
1593:aromatic
1508:coal tar
1484:aromatic
1482:. As an
1390:250 ppm
1215:NFPA 704
1062:Hazards
794:(χ)
772:constant
587:alcohols
177:1421310
37:Naphtali
7900:Kerogen
7787:Related
7730:Glycine
7683:Propyne
7642:Ammonia
7540:Benzene
7535:Acetone
7527:or more
7498:Propene
7483:Ethanol
7373:Propyne
7192:Methane
7061:Ketenyl
7011:Ammonia
6469:Truxene
6449:Rubrene
6439:Ovalene
6351:6 rings
6254:5 rings
6193:4 rings
6152:3 rings
6138:Azulene
6126:2 rings
6024:Benzene
5998:Styrene
5875:-Cymene
5867:-Cymene
5859:-Cymene
5848:Cymenes
5739:-Xylene
5731:-Xylene
5723:-Xylene
5712:Xylenes
5693:Toluene
5626:Azulene
5225:Heptyne
5215:Pentyne
5205:Propyne
5170:Alkynes
5095:Heptene
5085:Pentene
5075:Propene
5041:Alkenes
4963:Sterane
4929:Decalin
4917:Housane
4731:Heptane
4721:Pentane
4711:Propane
4701:Methane
4671:Alkanes
4482:6 March
4469:Epa.gov
4446:6 March
4441:Cdc.gov
4170:Bibcode
4168:: 389.
3914:Bibcode
3867:Bibcode
3793:Bibcode
3634:6376602
3573:"#0439"
3161:Decalin
3148:Camphor
3128:
2870:1.6552
2730:camphor
2669:rabbits
2644:of the
2627:adenoma
2617:The US
2602:in the
2580:fatigue
2501:decalin
2313:Solvent
2303:insects
2263:-xylene
2234:fungus
2185:Ukraine
2169:Koppers
2130:phenols
1978:decalin
1792:alkenes
1741:), and
1668:azulene
1659:Azulene
1638:isomers
1562:(PAH).
1548:benzene
1528:benzene
1520:naphtha
1498:History
1488:benzene
1420:what is
1418: (
1018:(Δ
966:entropy
836:1.5898
808:98 kPa:
774: (
646:ethanol
635:aniline
631:toluene
591:ammonia
521:Density
495:128.174
313:PubChem
136:91-20-3
29:naphtha
7951:Tholin
7772:Pyrene
7217:Silane
7187:Ketene
6689:Oxygen
6337:Picene
6230:Pyrene
5893:Durene
5812:Cumene
5661:Pyrene
5577:Acenes
5459:Dienes
5240:Decyne
5235:Nonyne
5230:Octyne
5220:Hexyne
5210:Butyne
5200:Ethyne
5110:Decene
5105:Nonene
5100:Octene
5090:Hexene
5080:Butene
5070:Ethene
4968:Cubane
4746:Decane
4741:Nonane
4736:Octane
4726:Hexane
4716:Butane
4706:Ethane
4421:24 May
4332:
4261:
4061:
3968:
3932:
3885:
3811:
3675:
3640:
3632:
3513:
3337:
3232:
3153:Dialin
3116:170.25
3098:1.670
3086:207.07
3065:1.643
3053:162.62
3032:1.632
3020:162.62
2999:1.593
2987:146.16
2954:173.17
2922:156,18
2891:144,17
2854:190.63
2825:172.18
2790:172.18
2671:, and
2606:, and
2588:nausea
2528:) and
2426:Alkyl
2331:durene
2181:Russia
2150:indene
2146:indane
2126:acidic
2060:+ 2 H
2024:gives
1786:using
1441:is an
1415:verify
1412:
1155:Danger
706:hexane
445:SMILES
301:C00829
203:ChEMBL
96:Names
7937:(PAH)
7525:atoms
7460:atoms
7400:atoms
7398:Eight
7328:atoms
7326:Seven
7234:atoms
7128:atoms
6998:atoms
6986:Water
6916:Ozone
6858:(HNC)
6852:(HCN)
6485:Acene
6055:Other
6040:trans
6017:Other
5956:Other
5912:Other
5805:Other
5748:Other
5619:Other
5543:Enyne
5511:Other
5007:Other
4476:(PDF)
4465:(PDF)
3809:S2CID
3755:(PDF)
3748:(PDF)
3673:S2CID
3638:S2CID
3405:â446.
3272:(PDF)
3125:0.987
3095:1.489
3062:1.138
3029:1.194
2996:1.323
2957:53â57
2900:1.224
2894:94â96
2867:1.265
2857:16â19
2828:185.5
2726:China
2612:liver
2604:urine
2600:blood
2484:Many
2476:is a
2384:Many
2340:with
2299:attic
2297:, in
2287:moths
2134:basic
2044:â C
1927:, NaC
1862:H + H
1630:alpha
1597:diene
1567:IUPAC
1556:fused
1348:NIOSH
1305:(TLV)
1296:5.9%
747:3.34
410:InChI
286:3347
183:ChEBI
149:JSmol
35:, or
7458:Nine
7126:Five
7036:HCCN
6996:Four
6956:SiNC
5936:tert
5568:PAHs
4484:2022
4448:2022
4423:2013
4363:help
4343:2008
4330:ISBN
4310:2005
4259:PMID
4222:2021
4059:PMID
3966:ISBN
3930:ISSN
3883:ISSN
3630:PMID
3511:ISBN
3335:ISBN
3250:link
3230:ISBN
3056:59.5
2963:1.22
2862:Torr
2746:Name
2673:mice
2665:rats
2651:The
2646:lung
2637:and
2629:and
2441:are
2421:dyes
2415:The
2392:and
2368:for
2329:and
2250:Uses
2226:and
2216:deer
2052:(CO)
1778:and
1714:exp(
1634:beta
1384:IDLH
1207:P501
1203:P281
1199:P273
1195:P210
1181:H410
1177:H351
1173:H302
1169:H228
740:log
511:Odor
353:UNII
292:KEGG
7749:NCO
7649:ion
7556:, C
7523:Ten
7232:Six
7138:ion
5928:sec
5185:â 2
4686:+ 2
4249:doi
4188:hdl
4178:doi
4139:doi
4110:doi
4049:doi
4045:148
3996:doi
3922:doi
3875:doi
3836:doi
3801:doi
3789:258
3732:149
3706:doi
3702:137
3665:doi
3661:111
3622:doi
3403:443
3222:doi
3122:128
3119:143
3092:279
3059:256
3026:259
2993:215
2990:â19
2960:340
2925:1â2
2897:278
2851:ClO
2796:300
2793:157
2724:In
2614:).
2536:).
2532:(a
2524:(a
2457:or
2410:CFT
2350:DDQ
2163:In
2076:or
2020:as
2001:).
1850:â C
1842:+ C
1802:or
1794:or
1762:In
1506:of
1371:REL
1358:PEL
1107:GHS
1099:air
1050:298
1001:298
974:298
885:/b
724:in
704:in
684:in
664:in
644:in
617:CCl
379:EPA
326:931
316:CID
232:906
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7566:70
7558:60
7554:60
7552:(C
7277:HC
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3077:10
3050:Cl
3044:10
3023:â6
3017:Cl
3011:10
2978:10
2966:â
2948:NO
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2913:11
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919:a
897:C
883:1
832:)
830:D
827:n
825:(
781:)
779:H
776:k
742:P
626:2
619:4
612:2
605:6
603:H
601:6
599:C
483:8
480:H
474:C
381:)
377:(
151:)
39:.
20:)
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