2638:. Having heard of these developments, and having previously experimented with other chemicals for antiseptic purposes without much success, Lister decided to try carbolic acid as a wound antiseptic. He had his first chance on August 12, 1865, when he received a patient: an eleven-year-old boy with a tibia bone fracture which pierced the skin of his lower leg. Ordinarily, amputation would be the only solution. However, Lister decided to try carbolic acid. After setting the bone and supporting the leg with splints, he soaked clean cotton towels in undiluted carbolic acid and applied them to the wound, covered with a layer of tin foil, leaving them for four days. When he checked the wound, Lister was pleasantly surprised to find no signs of infection, just redness near the edges of the wound from mild burning by the carbolic acid. Reapplying fresh bandages with diluted carbolic acid, the boy was able to walk home after about six weeks of treatment.
2389:
448:
323:
1506:
826:
821:
816:
929:
925:
1656:
1609:
2336:
88:
1665:
112:
97:
1974:
1249:
69:
60:
2005:: Compared to most other processes, the cumene process uses mild conditions and inexpensive raw materials. For the process to be economical, both phenol and the acetone by-product must be in demand. In 2010, worldwide demand for acetone was approximately 6.7 million tonnes, 83 percent of which was satisfied with acetone produced by the cumene process.
930:
2854:
for oral toxicity is less than 500 mg/kg for dogs, rabbits, or mice; the minimum lethal human dose was cited as 140 mg/kg. The Agency for Toxic
Substances and Disease Registry (ATSDR), U.S. Department of Health and Human Services states the fatal dose for ingestion of phenol is from 1 to 32
2846:
Since phenol is absorbed through the skin relatively quickly, systemic poisoning can occur in addition to the local caustic burns. Resorptive poisoning by a large quantity of phenol can occur even with only a small area of skin, rapidly leading to paralysis of the central nervous system and a severe
2657:
Before antiseptic operations were introduced at the hospital, there were sixteen deaths in thirty-five surgical cases. Almost one in every two patients died. After antiseptic surgery was introduced in the summer of 1865, there were only six deaths in forty cases. The mortality rate had dropped from
2642:
By 16 March 1867, when the first results of Lister's work were published in the Lancet, he had treated a total of eleven patients using his new antiseptic method. Of those, only one had died, and that was through a complication that was nothing to do with Lister's wound-dressing technique. Now, for
2550:
tube placement, as an alternative to general anesthesia or other local anesthetics. It also has hemostatic and antiseptic qualities that make it ideal for this use. Phenol spray, usually at 1.4% phenol as an active ingredient, is used medically to treat sore throat. It is the active ingredient in
1620:
with its unstable keto tautomer cyclohexadienone, but the effect is nearly negligible. The equilibrium constant for enolisation is approximately 10, which means only one in every ten trillion molecules is in the keto form at any moment. The small amount of stabilisation gained by exchanging a C=C
2572:
2686:
The toxic effect of phenol on the central nervous system causes sudden collapse and loss of consciousness in both humans and animals; a state of cramping precedes these symptoms because of the motor activity controlled by the central nervous system. Injections of phenol were used as a means of
4131:: Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage. (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acid, because benzene is found in illuminating gas.)
2617:
in his pioneering technique of antiseptic surgery. Lister decided that the wounds had to be thoroughly cleaned. He then covered the wounds with a piece of rag or lint covered in phenol. The skin irritation caused by continual exposure to phenol eventually led to the introduction of aseptic
928:
1443:, is far more water-soluble. It is a combustible solid (NFPA rating = 2). When heated, phenol produces flammable vapors that are explosive at concentrations of 3 to 10% in air. Carbon dioxide or dry chemical extinguishers should be used to fight phenol fires.
3057:
Kütt, Agnes; Movchun, Valeria; Rodima, Toomas; et al. (2008). "Pentakis(trifluoromethyl)phenyl, a
Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of Pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline".
2795:
Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract. Its corrosive effect on skin and mucous membranes is due to a protein-degenerating effect. Repeated or prolonged skin contact with phenol may cause
1695:
Phenol is so strongly activated that bromination and chlorination lead readily to polysubstitution. The reaction affords 2- and 4-substituted derivatives. The regiochemistry of halogenation changes in strongly acidic solutions where
4826:
Pullin, TG; Pinkerton, MN; Johnston, RV; Kilian, DJ (1978). "Decontamination of the skin of swine following phenol exposure: a comparison of the relative efficacy of water versus polyethylene glycol/industrial methylated spirits".
1659:
Neutral phenol substructure "shape". An image of a computed electrostatic surface of neutral phenol molecule, showing neutral regions in green, electronegative areas in orange-red, and the electropositive phenolic proton in
1563:
10.0). Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute little to its stabilization. However, the situation changes when solvation effects are excluded.
1538:; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp system compared to an sp system allows for great stabilization of the oxyanion. In support of the second explanation, the
2622:
in sterilizing various biological media. He theorized that if germs could be killed or prevented, no infection would occur. Lister reasoned that a chemical could be used to destroy the micro-organisms that cause infection.
1621:
bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity. Phenol therefore exists essentially entirely in the enol form. 4, 4' Substituted cyclohexadienone can undergo a
1704:
predominates. Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, additional nitro groups are introduced, e.g. to give
2671:
Phenol was the main ingredient of the "carbolic smoke ball," an ineffective device marketed in London in the 19th century as protection against influenza and other ailments, and the subject of the famous law case
4788:
Hunter, DM; Timerding, BL; Leonard, RB; McCalmont, TH; Schwartz, E (1992). "Effects of isopropyl alcohol, ethanol, and polyethylene glycol/industrial methylated spirits in the treatment of acute phenol burns".
946:
834:
3950:
796:
2507:
used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings. Due to safety concerns, phenol is banned from use in cosmetic products in the
3975:
3661:
1647:. Under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a "hard" nucleophile whereas the alpha-carbon positions tend to be "soft".
2598:
extracted phenol in its pure form, as a derivative of benzene, in 1841. In 1836, Auguste
Laurent coined the name "phène" for benzene; this is the root of the word "phenol" and "
2701:. The Germans learned that extermination of smaller groups was more economical by injection of each victim with phenol. Phenol injections were given to thousands of people.
4684:
Hanscha, Corwin; McKarns, Susan C; Smith, Carr J; Doolittle, David J (June 15, 2000). "Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity".
3630:
2535:. The procedure was first described by Otto Boll in 1945. Since that time phenol has become the chemical of choice for chemical matrixectomies performed by podiatrists.
900:
931:
4929:
3160:
3043:
1112:
741:
3414:
Arnold, Richard T.; Buckley, Jay S. (1 May 1949). "The
Dienone-Phenol Rearrangement. II. Rearrangement of 1-Keto-4-methyl-4-phenyl-1,4-dihydronaphthalene".
3713:
Lee, Byungik; Naito, Hiroto; Nagao, Masahiro; Hibino, Takashi (9 July 2012). "Alternating-Current
Electrolysis for the Production of Phenol from Benzene".
2889:
purification). Phenol is also a reproductive toxin causing increased risk of miscarriage and low birth weight indicating retarded development in utero.
5688:
1262:
3747:
Wittcoff, H.A., Reuben, B.G. Industrial
Organic Chemicals in Perspective. Part One: Raw Materials and Manufacture. Wiley-Interscience, New York. 1980.
4082:: 65-78. On page 69 of volume 31, Runge names phenol "Karbolsäure" (coal-oil-acid, carbolic acid). Runge characterizes phenol in: F. F. Runge (1834)
3836:
3520:
3185:
1810:
4509:
sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as sole carbon sources".
2320:
1965:
Because of phenol's commercial importance, many methods have been developed for its production, but the cumene process is the dominant technology.
3686:
Parmon, V. N.; Panov, G. I.; Uriarte, A.; Noskov, A. S. (2005). "Nitrous oxide in oxidation chemistry and catalysis application and production".
953:
3869:
5426:
4897:
3665:
4313:
494:
4922:
1530:
carbon atoms through the pi system. An alternative explanation involves the sigma framework, postulating that the dominant effect is the
3925:
3350:
Capponi, Marco; Gut, Ivo G.; Hellrung, Bruno; Persy, Gaby; Wirz, Jakob (1999). "Ketonization equilibria of phenol in aqueous solution".
1439:). Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. The sodium salt of phenol,
4296:
2590:. Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid). Coal tar remained the primary source until the development of the
1713:
of phenol and its derivatives often proceed without catalysts. Alkylating agents include alkyl halides, alkenes, and ketones. Thus,
3308:
Laurence, C. and Gal, J-F. Lewis
Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
3475:
3441:
Sergei M. Lukyanov, Alla V. Koblik (2003). "Tautomeric
Equilibria and Rearrangements Involving Phenols". In Zvi Rappoport (ed.).
2531:. Concentrated phenol liquids are used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical
4915:
3634:
4430:
5370:
3398:
3266:
2988:
2674:
1957:
Phenol and its derivatives react with iron(III) chloride to give intensely colored solutions containing phenoxide complexes.
698:
4391:
1673:
3901:
3318:
Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases".
5108:
3853:
3537:
3202:
5668:
5419:
4238:
4213:
4185:
3288:
3235:
2406:
The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics.
462:
2190:
in the early 1900s, based on discoveries by Wurtz and Kekule. The method involves the reaction of strong base with
939:
5387:
5209:
2481:
1622:
4141:
1269:
1257:
4071:
4753:
Brown, VKH; Box, VL; Simpson, BJ (1975). "Decontamination procedures for skin exposed to phenolic substances".
3570:
3458:
2873:, or perhaps even copious amounts of water. Removal of contaminated clothing is required, as well as immediate
2643:
the first time, patients with compound fractures were likely to leave the hospital with all their limbs intact
2618:(germ-free) techniques in surgery. Lister's work was inspired by the works and experiments of his contemporary
2603:
3807:
Kaeding, Warren W. (1 September 1964). "Oxidation of
Aromatic Acids. IV. Decarboxylation of Salicylic Acids".
5162:
4902:
3759:
Franck, H.-G., Stadelhofer, J.W. Industrial
Aromatic Chemistry. Springer-Verlag, New York. 1988. pp. 148-155.
3352:
2174:
Early methods relied on extraction of phenol from coal derivatives or the hydrolysis of benzene derivatives.
1814:
1751:
Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Phenol is neutralized by
1451:
Phenol is a weak acid (pH 6.6). In aqueous solution in the pH range ca. 8 - 12 it is in equilibrium with the
136:
17:
3553:
V. Prakash Reddy. G. K. Surya Prakash (2003). "Electrophilic reactions of phenols". In Zvi Rappoport (ed.).
5663:
5412:
4791:
2878:
2769:
2478:
2307:
These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride byproduct.
882:
391:
318:
1668:
Phenol water phase diagram: Certain combinations of phenol and water can make two solutions in one bottle.
4083:
3587:
3256:
2820:
may be affected as well. Long-term or repeated exposure of the substance may have harmful effects on the
2576:
1628:
For substituted phenols, several factors can favor the keto tautomer: (a) additional hydroxy groups (see
1527:
426:
4017:
892:
825:
260:
5515:
5356:
2972:
2253:
1539:
1144:
1123:
658:
4378:
2503:
Phenol is so inexpensive that it also attracts many small-scale uses. It is a component of industrial
2346:
salts hydrolyze to phenol. The method is of no commercial interest since the precursor is expensive.
1204:
896:
5678:
2705:
was also murdered with a phenol injection after surviving two weeks of dehydration and starvation in
2583:
1710:
3876:
2721:
Phenol is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine. The
1725:
give respectively 4-adamantylphenol, a bis(2-hydroxyphenyl) derivative, and a 4-cyclohexylphenols.
5683:
5495:
5194:
443:
4649:
World Health Organization/International Labour Organization: International Chemical Safety Cards,
4123:
Auguste Laurent (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique,"
2695:. It was originally used by the Nazis in 1939 as part of the mass-murder of disabled people under
5375:
3606:
3299:
Drago, R S. Physical Methods For Chemists, (Saunders College Publishing 1992), ISBN 0-03-075176-4
2928:
2195:
1596:
IR frequency shifts accompanying adduct formation have been compiled. Phenol is classified as a
1519:
30:
This article is about the molecule. For the group of chemicals that contains a phenol group, see
4321:
2804:. The substance may cause harmful effects on the central nervous system and heart, resulting in
5321:
5228:
4277:
3336:
The plots shown in this paper used older parameters. Improved E&C parameters are listed in
2783:
2710:
2591:
2388:
1384:
1326:
874:
815:
5535:
5476:
5471:
5233:
5175:
5170:
4128:
2969:
Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2933:
2407:
2198:
to give sodium phenoxide. Acidification of the latter gives phenol. The net conversion is:
1617:
1535:
1376:
848:
808:
627:
4466:
gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate"
4460:
Juteau, P.; Côté, V; Duckett, MF; Beaudet, R; Lépine, F; Villemur, R; Bisaillon, JG (2005).
4407:
220:
5658:
5489:
5287:
5238:
5204:
5188:
5118:
4836:
4693:
4518:
4291:
3902:"Prohibited substances in cosmetic product (Annex II, #1175, Phenol) - European Commission"
2249:
2021:
1573:
1509:
820:
400:
124:
4877:
4727:
4103:
4047:
3134:
8:
5485:
5326:
5184:
4964:
4872:
4650:
4114:: 195-228. On page 198, Laurent names phenol "hydrate de phényle" and "l'acide phénique".
2943:
2877:
treatment for large splashes. This is particularly important if the phenol is mixed with
2866:
2805:
2760:. This amount is different from and presumably higher than the amount in the distillate.
2474:
2096:
2024:. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and
1726:
1436:
1420:
280:
196:
186:
4840:
4697:
4522:
447:
322:
240:
5540:
5258:
4360:
3789:
3015:
2848:
2002:
1760:
4907:
4848:
4804:
4705:
4348:
3497:
5673:
5341:
5300:
5219:
4996:
4852:
4808:
4770:
4709:
4632:
4627:
4610:
4591:
4534:
4487:
4352:
4234:
4209:
4181:
4162:
3849:
3730:
3566:
3533:
3480:
3454:
3394:
3284:
3262:
3231:
3198:
3075:
2984:
2870:
2778:
2749:
2485:
2009:
1902:
1718:
1714:
1518:
Phenol is more acidic than aliphatic alcohols. Its enhanced acidity is attributed to
1416:
1198:
4364:
3793:
5598:
4844:
4800:
4766:
4762:
4701:
4622:
4583:
4526:
4477:
4438:
4344:
3841:
3816:
3781:
3722:
3695:
3558:
3557:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 605–660.
3525:
3489:
3446:
3445:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 713–838.
3423:
3378:
3360:
3327:
3223:
3190:
3067:
2976:
2916:
2800:, or even second and third-degree burns. Inhalation of phenol vapor may cause lung
2702:
2692:
2631:
2556:
2191:
2092:
1806:
1802:
1764:
1752:
1531:
1440:
1304:
1300:
1228:
904:
782:
772:
762:
752:
608:
517:
4663:
3845:
3529:
3194:
2465:
Phenol is also a versatile precursor to a large collection of drugs, most notably
5550:
5530:
5113:
5035:
4969:
4300:
3699:
2595:
2492:
from tissues or cell culture samples. Depending on the pH of the solution either
2343:
1589:
975:
718:
42:
4587:
4530:
4335:
Rasmussen, L.E.L; Perrin, Thomas E (1999). "Physiological Correlates of Musth".
4303:, Chapter 14, Killing with Syringes: Phenol Injections. By Dr. Robert Jay Lifton
3976:"Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients - Canada.ca"
3104:
2980:
364:
5505:
5466:
5381:
5277:
5142:
4560:
2912:
2730:
2722:
2508:
2504:
2427:
2395:
1986:
1768:
1577:
1505:
1240:
888:
688:
640:
4887:
3999:
3039:
2836:
effects, another mechanism for the toxicity of phenol may be the formation of
1367:, but today is produced on a large scale (about 7 million tonnes a year) from
1076:
1034:
999:
5652:
5560:
5500:
5089:
5060:
5001:
4377:
Musth in elephants. Deepa Ananth, Zoo's print journal, 15(5), pages 259-262 (
3493:
3386:
3382:
3152:
3130:
2858:
2619:
2614:
2528:
2439:
2435:
2415:
2245:
2163:
2159:
2081:
2025:
2017:
1756:
1730:
1722:
1585:
1388:
1357:
1345:
597:
587:
311:
38:
5404:
3450:
2088:. Routes for the generation of nitrous oxide however remain uncompetitive.
5637:
5439:
5351:
5147:
5055:
5040:
5016:
4946:
4942:
4892:
4713:
4595:
4538:
4491:
4356:
3785:
3734:
3726:
3562:
3364:
3079:
2840:
2774:
2745:
2744:
Phenol is a measurable component in the aroma and taste of the distinctive
2688:
2552:
2538:
Concentrated liquid phenol can be used topically as a local anesthetic for
2532:
2489:
2459:
2423:
2324:
2155:
2107:
1978:
1898:
1681:
1680:
density from O into the ring. Many groups can be attached to the ring, via
1526:
anion. In this way, the negative charge on oxygen is delocalized on to the
1379:
to many materials and useful compounds. It is primarily used to synthesize
1330:
777:
767:
757:
747:
4812:
4774:
4636:
4482:
4461:
4390:
The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (
2658:
almost 50 per cent to around 15 per cent. It was a remarkable achievement
952:
5588:
5573:
5510:
5481:
5456:
5248:
5180:
5137:
5006:
4856:
3252:
3183:
Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Phenol".
2833:
2547:
2543:
2455:
2451:
2411:
2152:
The reaction is proposed to proceed via formation of benzyoylsalicylate.
2110:, involves copper-catalyzed reaction of molten sodium benzoate with air:
1706:
1689:
1677:
1644:
1597:
1396:
1297:
965:
4882:
4661:
3820:
3427:
1871:
dust or when its vapour is passed over granules of zinc at 400 °C:
938:
300:
5606:
5578:
5568:
5525:
5520:
5448:
5336:
5295:
5253:
5152:
5080:
5065:
5011:
4938:
3227:
2948:
2862:
2797:
2610:
2524:
1734:
1629:
1432:
1223:
945:
542:
271:
3331:
3071:
2919:
of which the phenol discussed in this article is the simplest member.
1655:
5621:
5616:
5243:
5199:
5128:
5070:
5050:
4984:
4974:
4003:
3552:
3337:
2787:
is a bacterium species able to degrade phenol as sole carbon source.
2738:
2706:
2697:
2470:
2447:
2084:
is a potentially "green" oxidant that is a more potent oxidant than O
1685:
1523:
1412:
1408:
1372:
1368:
862:
411:
4557:
The Merck Index: An Encyclopedia of Chemical, Drugs, and Biologicals
1556:
in water is 10.9, making it only slightly less acidic than phenol (p
1239:
Except where otherwise noted, data are given for materials in their
5583:
5461:
5331:
4955:
4611:"Cardiac dysrhythmias associated with chemical peeling with phenol"
2908:
2907:
is also used to refer to any compound that contains a six-membered
2874:
2837:
2726:
2627:
2587:
2571:
2431:
2335:
2187:
2035:
2013:
1737:
1633:
1608:
1581:
1435:
in water, with about 84.2 g dissolving in 1000 ml (0.895
1400:
1380:
1364:
911:
339:
291:
3440:
3037:
1664:
870:
219:
87:
5611:
5305:
4988:
4903:
Arcane Radio Trivia outlines competing uses for Phenol circa 1915
4470:
International Journal of Systematic and Evolutionary Microbiology
3222:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons.
2898:
2809:
2635:
2539:
2466:
2422:
resins. Condensation of phenol, alkylphenols, or diphenols with
2103:
2041:
1916:
is obtained as the main product and nitrogen gas as a byproduct.
1913:
1864:
1741:
1640:
1553:
1319:
573:
351:
111:
31:
4734:. U.S. Department of Health and Human Services. October 21, 2014
3258:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
96:
5435:
5268:
5099:
4787:
4021:
2938:
2829:
2825:
2817:
2757:
2753:
2599:
2560:
2512:
1998:
1745:
1353:
251:
2055:) to phenol is possible, but it has not been commercialized:
5346:
4825:
4576:
Burns: Journal of the International Society for Burn Injuries
4025:
3473:
3250:
3157:
Immediately Dangerous to Life or Health Concentrations (IDLH)
2821:
2801:
2741:. This compound is ingested from the plants the beaver eats.
2734:
2443:
2419:
2183:
2029:
1994:
1625:
in acid conditions and form stable 3,4‐disubstituted phenol.
1455:
1404:
1392:
1322:
728:
375:
231:
209:
4683:
3772:
Kazem-Rostami, Masoud (2017). "Amine to phenol conversion".
1973:
431:
4574:
Lin TM, Lee SS, Lai CS, Lin SD (June 2006). "Phenol burn".
4320:. Linz, Austria: Johannes Kepler University. Archived from
3377:
3003:-OH, both as a preferred name and for general nomenclature.
2813:
2316:
1868:
1755:
forming sodium phenate or phenolate, but being weaker than
1549:
1182:
563:
330:
68:
4199:
4197:
59:
3056:
2886:
2882:
2497:
2493:
1676:. The enhanced nucleophilicity is attributed to donation
4459:
4151:: 215-229. Gerhardt coins the name "phénol" on page 221.
3685:
3317:
3182:
3107:. PubChem, US National Library of Medicine. 10 June 2023
858:
37:"Carbolic acid" redirects here. Not to be confused with
4937:
4194:
3349:
2713:. Approximately one gram is sufficient to cause death.
4893:
CDC - Phenol - NIOSH Workplace Safety and Health Topic
4651:
http://www.inchem.org/documents/icsc/icsc/eics0070.htm
3393:(1st ed.). Oxford University Press. p. 531.
3834:
Musser, Michael T. "Cyclohexanol and Cyclohexanone".
3601:
3599:
3161:
National Institute for Occupational Safety and Health
3044:
National Institute for Occupational Safety and Health
2177:
4084:"Ueber einige Produkte der Steinkohlendestillation,"
3827:
2737:. It is also one of the chemical compounds found in
2008:
A route analogous to the cumene process begins with
1356:, it requires careful handling because it can cause
4072:"Ueber einige Produkte der Steinkohlendestillation"
3926:"CosIng - Cosmetics - GROWTH - European Commission"
3712:
1371:-derived feedstocks. It is an important industrial
4728:"Medical Management Guidelines for Phenol (C6H6O)"
4267:. Vol. 25. Wiley-VCH. 2003. pp. 589–604.
3679:
3607:"Phenol -- The essential chemical industry online"
3596:
2881:(a commonly used mixture in molecular biology for
2634:using carbolic acid to reduce the smell of sewage
2028:. Cyclohexanone is an important precursor to some
4163:"Antiseptic Principle Of The Practice Of Surgery"
2450:are produced by alkylation of phenol to give the
5650:
4732:Agency for Toxic Substances and Disease Registry
3625:
3623:
2865:exposures can be decontaminated by washing with
2036:Oxidation of benzene, toluene, cyclohexylbenzene
854:
363:
4883:National Pollutant Inventory: Phenol Fact Sheet
4752:
4334:
2194:, proceeding by the reaction of hydroxide with
2182:The original commercial route was developed by
2162:. Decomposition of this hydroperoxide affords
1985:Accounting for 95% of production (2003) is the
1748:and cumyl phenols can be produced in that way.
1636:, and (c) deprotonation to give the phenolate.
1383:and related materials. Phenol and its chemical
927:
195:
4662:U.S. Department of Health and Human Services.
4265:Ullmann's Encyclopedia of Industrial Chemistry
3870:"CH207 Aircraft paintstripper, phenolic, acid"
3837:Ullmann's Encyclopedia of Industrial Chemistry
3521:Ullmann's Encyclopedia of Industrial Chemistry
3518:Muller F, Caillard L (2011). "Chlorophenols".
3517:
3261:(6th ed.), New York: Wiley-Interscience,
3186:Ullmann's Encyclopedia of Industrial Chemistry
2240:
1592:. The enthalpies of adduct formation and the
866:
5434:
5420:
4923:
3875:. Callington. 14 October 2009. Archived from
3771:
3655:
3653:
3651:
3620:
3474:David Y. Curtin & Allan R. Stein (1966).
3413:
3217:
2630:, England, officials were experimenting with
4608:
4573:
4504:
602:181.7 °C (359.1 °F; 454.8 K)
3664:. American Chemical Society. Archived from
592:40.5 °C (104.9 °F; 313.6 K)
5427:
5413:
4930:
4916:
4228:
4203:
4175:
3648:
2828:. There is no evidence that phenol causes
2752:, but it can be over 160ppm in the malted
2387:
2315:Phenol is also a recoverable byproduct of
1431:Phenol is an organic compound appreciably
446:
321:
279:
5689:Substances discovered in the 19th century
4626:
4481:
4408:"Peat, Phenol and PPM, by Dr P. Brossard"
4271:
4106:(Memoir on benzene and its derivatives),
4074:(On some products of coal distillation),
3951:"Cosmetic Ingredient Hotlist - Canada.ca"
3755:
3753:
3592:. London: Macmillan & Co. p. 23.
3589:A treatise on chemistry, Volume 3, Part 3
3178:
3176:
3174:
3172:
3170:
3099:
3097:
3095:
3093:
3091:
3089:
2586:, who extracted it (in impure form) from
1580:with a wide range of Lewis bases such as
399:
4554:
4550:
4548:
4306:
4208:. BBC Books - Random House. p. 62.
4180:. BBC Books - Random House. p. 61.
3741:
3038:NIOSH Pocket Guide to Chemical Hazards.
2995:Only one name is retained, phenol, for C
2960:
2570:
2334:
2330:
2248:can be hydrolyzed to phenol using base (
1972:
1663:
1654:
1632:) (b) annulation as in the formation of
1607:
1504:
4873:International Chemical Safety Card 0070
4402:
4400:
4285:
4233:. BBC Books - Randomhouse. p. 63.
4104:"Mémoire sur le phényle et ses dérivés"
3806:
3715:Angewandte Chemie International Edition
3659:
3126:
3124:
3122:
2709:when he volunteered to die in place of
2575:Bottle of Calvert's phenol antiseptic,
1977:The Hock process leading to phenol via
471:InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
442:
299:
14:
5651:
4888:NIOSH Pocket Guide to Chemical Hazards
4453:
4318:Auschwitz: Final Station Extermination
4160:
3973:
3948:
3750:
3585:
3167:
3147:
3145:
3143:
3086:
3033:
3031:
3029:
3027:
3025:
3008:
2613:properties of phenol were used by Sir
2527:, and it is used in the production of
481:InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
312:
5408:
4911:
4545:
4505:Rehfuss, Marc; Urban, James (2005). "
3767:
3765:
3546:
2773:is a bacterium species that produces
2675:Carlill v Carbolic Smoke Ball Company
1813:is formed. This is an example of the
970:79 °C (174 °F; 352 K)
474:Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
259:
239:
4397:
4258:
4256:
4254:
4252:
4250:
4231:Blood and Guts: A History of Surgery
4206:Blood and Guts: A History of Surgery
4178:Blood and Guts: A History of Surgery
3476:"2,6,6-Trimethyl-2,4-Cyclohexadione"
3119:
2915:(-OH). Thus, phenols are a class of
2664:Blood and Guts: A History of Surgery
2649:Blood and Guts: A History of Surgery
1733:alkylate phenols in the presence of
781:
771:
761:
751:
4511:Systematic and Applied Microbiology
3140:
3022:
2681:
1674:electrophilic aromatic substitution
1612:Phenol-cyclohexadienone tautomerism
1567:
354:
338:
24:
5109:Iodine/octylphenoxypolyglycolether
4664:"How can phenol affect my health?"
4314:"Killing through phenol injection"
3833:
3762:
3662:"What's New in Phenol Production?"
3660:Plotkin, Jeffrey S. (2016-03-21).
2729:showed the presence of phenol and
2178:Hydrolysis of benzenesulfonic acid
923:
95:
86:
67:
58:
25:
5700:
4878:Phenol Material Safety Data Sheet
4866:
4247:
2763:
2582:Phenol was discovered in 1834 by
2310:
1968:
1805:are shaken in presence of dilute
1672:Phenol is highly reactive toward
5210:Didecyldimethylammonium chloride
4755:Archives of Environmental Health
4671:Toxicological Profile for Phenol
4628:10.1097/00000542-198503000-00030
4145:Annales de Chimie et de Physique
4125:Annales de Chemie et de Physique
4108:Annales de Chimie et de Physique
4052:collections.thackraymuseum.co.uk
3809:The Journal of Organic Chemistry
3060:The Journal of Organic Chemistry
2169:
1387:are essential for production of
1363:Phenol was first extracted from
1247:
824:
819:
814:
529:
110:
5301:Isopropanol (isopropyl alcohol)
4819:
4781:
4746:
4720:
4686:Chemico-Biological Interactions
4677:
4655:
4643:
4609:Warner, MA; Harper, JV (1985).
4602:
4567:
4498:
4423:
4384:
4371:
4328:
4222:
4169:
4154:
4134:
4117:
4096:
4064:
4040:
4010:
3992:
3967:
3942:
3918:
3894:
3862:
3800:
3706:
3579:
3511:
3467:
3434:
3407:
3371:
3343:
3311:
3302:
3293:
3274:
3244:
2430:, a famous example of which is
1576:and in alkane solvents, phenol
1243:(at 25 °C , 100 kPa).
5352:Chloramine-T (tosylchloramide)
4767:10.1080/00039896.1975.10666623
4048:"182.095 | Collections Online"
3211:
3050:
2973:The Royal Society of Chemistry
2847:drop in body temperature. The
2716:
2458:, which are then subjected to
2323:, the oxidation of toluene to
2158:of cyclohexylbenzene give the
1759:, it cannot be neutralized by
1603:
1534:from the more electronegative
558:Transparent crystalline solid
535:
523:
13:
1:
5163:Quaternary ammonium compounds
4849:10.1016/S0041-008X(78)80044-1
4805:10.1016/S0196-0644(05)81891-8
4706:10.1016/S0009-2797(00)00171-X
4349:10.1016/S0031-9384(99)00114-6
4142:"Recherches sur la salicine,"
4087:Annalen der Physik und Chemie
4076:Annalen der Physik und Chemie
3974:Canada, Health (2004-06-18).
3949:Canada, Health (2004-06-18).
3846:10.1002/14356007.a08_217.pub2
3530:10.1002/14356007.a07_001.pub2
3320:Journal of Chemical Education
3195:10.1002/14356007.a19_299.pub3
2954:
2551:some oral analgesics such as
2523:Phenol was widely used as an
1960:
1801:When a mixture of phenol and
1426:
1329:. The molecule consists of a
1117:(US health exposure limits):
4792:Annals of Emergency Medicine
4464:Cryptanaerobacter phenolicus
4229:Hollingham, Richard (2008).
4204:Hollingham, Richard (2008).
4176:Hollingham, Richard (2008).
4018:"How Does Our Lip Balm Work"
3700:10.1016/j.cattod.2004.12.012
2770:Cryptanaerobacter phenolicus
2482:phenol–chloroform extraction
2020:, akin to the production of
1897:When phenol is treated with
1650:
1623:dienone–phenol rearrangement
7:
4588:10.1016/j.burns.2005.12.016
4531:10.1016/j.syapm.2005.05.011
3218:Zvi Rappoport, ed. (2003).
2981:10.1039/9781849733069-FP001
2922:
2911:ring, bonded directly to a
2790:
2602:". In 1843, French chemist
2577:Thackray Museum of Medicine
2477:. Phenol is a component in
2241:Hydrolysis of chlorobenzene
2099:gives phenol from benzene.
2001:(isopropylbenzene) via the
1993:. It involves the partial
988:or concentration (LD, LC):
82:
54:
10:
5705:
5357:Octenidine dihydrochloride
4559:. Whitehouse Station, NJ:
4127:, vol. 63, pp. 27–45, see
3137:. Retrieved on 2022-02-15.
2896:
2892:
2606:coined the name "phénol".
2566:
2518:
2398:decarboxylates to phenol.
1867:when it is distilled with
1711:Friedel Crafts alkylations
1692:, and related processes.
1446:
36:
29:
5630:
5597:
5559:
5447:
5365:
5314:
5296:Propanol (propyl alcohol)
5286:
5267:
5218:
5161:
5127:
5098:
5079:
5025:
4983:
4954:
4555:Budavari, S, ed. (1996).
4337:Physiology & Behavior
4140:Gerhardt, Charles (1843)
3631:"Direct Routes to Phenol"
2584:Friedlieb Ferdinand Runge
2327:is conducted separately.
1815:Schotten–Baumann reaction
1237:
1209:
1111:
984:
795:
790:
734:
510:
490:
458:
179:
147:
135:
123:
118:
109:
81:
53:
27:Organic compound (C6H5OH)
5669:Hazardous air pollutants
4898:IARC Monograph: "Phenol"
3555:The Chemistry of Phenols
3494:10.15227/orgsyn.046.0115
3443:The Chemistry of Phenols
3220:The Chemistry of Phenols
2687:individual execution by
2040:The direct oxidation of
883:Precautionary statements
5306:Ethanol (ethyl alcohol)
4161:Lister, Joseph (1867).
4102:Auguste Laurent (1841)
3840:. Weinheim: Wiley-VCH.
3524:. Weinheim: Wiley-VCH.
3451:10.1002/0470857277.ch11
3189:. Weinheim: Wiley-VCH.
2929:Bamberger rearrangement
2832:in humans. Besides its
2401:
2196:sodium benzenesulfonate
1520:resonance stabilization
5516:Dichlorobenzyl alcohol
5457:Acriflavinium chloride
5322:Potassium permanganate
5229:Mercuric amidochloride
4829:Toxicol Appl Pharmacol
4507:Rhodococcus phenolicus
4437:. BDCL. Archived from
3786:10.1055/s-0036-1588180
3727:10.1002/anie.201202159
3586:Roscoe, Henry (1891).
3563:10.1002/0470857277.ch9
3365:10.1139/cjc-77-5-6-605
2784:Rhodococcus phenolicus
2669:
2662:— Richard Hollingham,
2654:
2647:— Richard Hollingham,
2592:petrochemical industry
2579:
2340:
2254:Raschig–Hooker process
1982:
1669:
1661:
1613:
1513:
1512:of the phenoxide anion
934:
680:29.1 (in acetonitrile)
100:
91:
72:
63:
5536:Myristyl-benzalkonium
5234:Phenylmercuric borate
5176:Benzethonium chloride
4483:10.1099/ijs.0.02914-0
3283:2nd Ed. John McMurry
2975:. 2014. p. 690.
2934:Claisen rearrangement
2655:
2640:
2574:
2414:, a key precursor to
2338:
2331:Miscellaneous methods
1976:
1863:Phenol is reduced to
1667:
1658:
1618:keto-enol tautomerism
1611:
1536:sp hybridised carbons
1508:
933:
137:Systematic IUPAC name
99:
90:
71:
62:
5205:Benzoxonium chloride
5119:Diiodohydroxypropane
4392:book at google books
4282:by Peter Tyson. NOVA
3882:on 23 September 2015
2542:procedures, such as
2475:pharmaceutical drugs
2192:benzenesulfonic acid
2022:cumene hydroperoxide
1707:2,4,6-trinitrophenol
1574:carbon tetrachloride
1510:Resonance structures
1421:pharmaceutical drugs
1077:median concentration
1048:mg/kg (rabbit, oral)
916:(fire diamond)
125:Preferred IUPAC name
5664:Commodity chemicals
5327:Sodium hypochlorite
4965:Ethacridine lactate
4841:1978ToxAP..43..199P
4698:2000CBI...127...61H
4523:2005SyApM..28..695R
4070:F. F. Runge (1834)
4028:on 18 February 2015
3821:10.1021/jo01032a016
3428:10.1021/ja01173a071
3251:Smith, Michael B.;
2944:Fries rearrangement
2867:polyethylene glycol
2746:Islay scotch whisky
2410:with acetone gives
2097:alternating current
1901:in the presence of
1715:adamantyl-1-bromide
1303:with the molecular
1020:mg/kg (mouse, oral)
609:Solubility in water
550: g/mol
50:
5392:Never to phase III
4299:2017-10-22 at the
3228:10.1002/0470857277
2725:secretion of male
2580:
2500:can be extracted.
2484:technique used in
2341:
2319:pyrolysis. In the
2106:, as developed by
2003:Hock rearrangement
1983:
1761:sodium bicarbonate
1670:
1662:
1614:
1514:
1417:phenoxy herbicides
1270:Infobox references
1210:Related compounds
1185:(Immediate danger)
935:
618:g/100 mL (20
101:
92:
73:
64:
48:
5646:
5645:
5599:Local anesthetics
5402:
5401:
5342:Hydrogen peroxide
5239:Mercuric chloride
4997:Dibrompropamidine
3780:(13): 1641–1645.
3721:(28): 6961–6965.
3694:(2005): 115–131.
3481:Organic Syntheses
3400:978-0-19-850346-0
3391:Organic Chemistry
3381:; Greeves, Nick;
3379:Clayden, Jonathan
3332:10.1021/ed054p612
3281:Organic Chemistry
3268:978-0-471-72091-1
3131:Sigma-Aldrich Co.
3072:10.1021/jo702513w
2990:978-0-85404-182-4
2917:organic compounds
2871:isopropyl alcohol
2779:4-hydroxybenzoate
2594:. French chemist
2486:molecular biology
2442:, a precursor to
2102:The oxidation of
2010:cyclohexylbenzene
1903:boron trifluoride
1719:dicyclopentadiene
1278:Chemical compound
1276:
1275:
1216:Related compounds
1199:Safety data sheet
1062:mg/kg (cat, oral)
1055:mg/kg (dog, oral)
1013:mg/kg (rat, oral)
849:Hazard statements
427:CompTox Dashboard
221:Interactive image
105:
104:
77:
76:
16:(Redirected from
5696:
5679:Phenyl compounds
5429:
5422:
5415:
5406:
5405:
4932:
4925:
4918:
4909:
4908:
4861:
4860:
4823:
4817:
4816:
4785:
4779:
4778:
4750:
4744:
4743:
4741:
4739:
4724:
4718:
4717:
4681:
4675:
4674:
4668:
4659:
4653:
4647:
4641:
4640:
4630:
4606:
4600:
4599:
4571:
4565:
4564:
4552:
4543:
4542:
4502:
4496:
4495:
4485:
4476:(Pt 1): 245–50.
4457:
4451:
4450:
4448:
4446:
4441:on 21 April 2016
4427:
4421:
4420:
4418:
4417:
4412:
4404:
4395:
4388:
4382:
4375:
4369:
4368:
4332:
4326:
4325:
4310:
4304:
4293:The Nazi Doctors
4289:
4283:
4275:
4269:
4268:
4260:
4245:
4244:
4226:
4220:
4219:
4201:
4192:
4191:
4173:
4167:
4166:
4158:
4152:
4138:
4132:
4121:
4115:
4100:
4094:
4068:
4062:
4061:
4059:
4058:
4044:
4038:
4037:
4035:
4033:
4024:. Archived from
4014:
4008:
4007:
3996:
3990:
3989:
3987:
3986:
3971:
3965:
3964:
3962:
3961:
3946:
3940:
3939:
3937:
3936:
3922:
3916:
3915:
3913:
3912:
3898:
3892:
3891:
3889:
3887:
3881:
3874:
3866:
3860:
3859:
3831:
3825:
3824:
3815:(9): 2556–2559.
3804:
3798:
3797:
3769:
3760:
3757:
3748:
3745:
3739:
3738:
3710:
3704:
3703:
3683:
3677:
3676:
3674:
3673:
3657:
3646:
3645:
3643:
3642:
3633:. Archived from
3627:
3618:
3617:
3615:
3614:
3603:
3594:
3593:
3583:
3577:
3576:
3550:
3544:
3543:
3515:
3509:
3508:
3506:
3505:
3496:. Archived from
3471:
3465:
3464:
3438:
3432:
3431:
3416:J. Am. Chem. Soc
3411:
3405:
3404:
3375:
3369:
3368:
3359:(5–6): 605–613.
3347:
3341:
3335:
3315:
3309:
3306:
3300:
3297:
3291:
3278:
3272:
3271:
3248:
3242:
3241:
3215:
3209:
3208:
3180:
3165:
3164:
3149:
3138:
3128:
3117:
3116:
3114:
3112:
3101:
3084:
3083:
3054:
3048:
3047:
3035:
3020:
3019:
3012:
3006:
3005:
2967:"Front Matter".
2964:
2777:from phenol via
2756:used to produce
2748:, generally ~30
2703:Maximilian Kolbe
2693:Second World War
2682:Second World War
2632:sewage treatment
2604:Charles Gerhardt
2438:of phenol gives
2391:
2384:
2303:
2278:
2236:
2215:H + 2 NaOH → C
2148:
2093:electrosynthesis
2077:
2054:
1953:
1911:
1893:
1859:
1807:sodium hydroxide
1803:benzoyl chloride
1797:
1765:sodium carbonate
1753:sodium hydroxide
1703:
1616:Phenol exhibits
1595:
1568:Hydrogen bonding
1499:
1468:
1441:sodium phenoxide
1351:
1343:
1318:. It is a white
1317:
1301:organic compound
1260:
1254:
1251:
1250:
1229:Sodium phenoxide
1192:
1172:
1168:
1161:
1157:
1137:
1133:
1103:
1096:
1089:
1061:
1054:
1047:
1035:lowest published
1019:
1012:
976:Explosive limits
955:
948:
941:
926:
906:
902:
898:
894:
890:
876:
872:
868:
864:
860:
856:
828:
823:
818:
785:
775:
765:
755:
727:
711:
674:9.95 (in water),
652:
648:
621:
617:
581:
568:Sweet and tarry
549:
537:
531:
525:
518:Chemical formula
451:
450:
435:
433:
403:
367:
356:
342:
325:
314:
303:
283:
263:
243:
223:
199:
171:Phenyl hydroxide
114:
83:
55:
51:
47:
21:
5704:
5703:
5699:
5698:
5697:
5695:
5694:
5693:
5684:1834 in science
5649:
5648:
5647:
5642:
5626:
5593:
5555:
5551:Povidone-iodine
5531:Hexylresorcinol
5496:Cetylpyridinium
5443:
5433:
5403:
5398:
5397:
5382:Clinical trials
5361:
5310:
5282:
5263:
5259:Mercuric iodide
5214:
5195:Cetylpyridinium
5157:
5123:
5114:Povidone-iodine
5094:
5075:
5036:Hexachlorophene
5029:and derivatives
5021:
4979:
4970:9-Aminoacridine
4950:
4936:
4869:
4864:
4824:
4820:
4786:
4782:
4751:
4747:
4737:
4735:
4726:
4725:
4721:
4682:
4678:
4666:
4660:
4656:
4648:
4644:
4607:
4603:
4572:
4568:
4553:
4546:
4503:
4499:
4458:
4454:
4444:
4442:
4431:"Bruichladdich"
4429:
4428:
4424:
4415:
4413:
4410:
4406:
4405:
4398:
4389:
4385:
4376:
4372:
4333:
4329:
4312:
4311:
4307:
4301:Wayback Machine
4290:
4286:
4279:The Experiments
4276:
4272:
4262:
4261:
4248:
4241:
4227:
4223:
4216:
4202:
4195:
4188:
4174:
4170:
4159:
4155:
4139:
4135:
4122:
4118:
4101:
4097:
4069:
4065:
4056:
4054:
4046:
4045:
4041:
4031:
4029:
4016:
4015:
4011:
3998:
3997:
3993:
3984:
3982:
3972:
3968:
3959:
3957:
3947:
3943:
3934:
3932:
3924:
3923:
3919:
3910:
3908:
3900:
3899:
3895:
3885:
3883:
3879:
3872:
3868:
3867:
3863:
3856:
3832:
3828:
3805:
3801:
3770:
3763:
3758:
3751:
3746:
3742:
3711:
3707:
3688:Catalysis Today
3684:
3680:
3671:
3669:
3658:
3649:
3640:
3638:
3629:
3628:
3621:
3612:
3610:
3605:
3604:
3597:
3584:
3580:
3573:
3551:
3547:
3540:
3516:
3512:
3503:
3501:
3472:
3468:
3461:
3439:
3435:
3412:
3408:
3401:
3376:
3372:
3348:
3344:
3316:
3312:
3307:
3303:
3298:
3294:
3279:
3275:
3269:
3249:
3245:
3238:
3216:
3212:
3205:
3181:
3168:
3151:
3150:
3141:
3129:
3120:
3110:
3108:
3103:
3102:
3087:
3055:
3051:
3036:
3023:
3014:
3013:
3009:
3002:
2998:
2991:
2966:
2965:
2961:
2957:
2925:
2901:
2895:
2852:
2793:
2766:
2719:
2684:
2596:Auguste Laurent
2569:
2521:
2505:paint strippers
2428:phenolic resins
2404:
2382:
2378:
2374:
2370:
2366:
2362:
2358:
2354:
2350:
2344:Phenyldiazonium
2339:Amine to phenol
2333:
2313:
2301:
2297:
2293:
2289:
2285:
2281:
2276:
2272:
2269:Cl + NaOH → C
2268:
2264:
2260:
2243:
2234:
2230:
2226:
2222:
2218:
2214:
2210:
2206:
2202:
2180:
2172:
2146:
2142:
2138:
2134:
2130:
2126:
2122:
2118:
2114:
2087:
2075:
2071:
2067:
2063:
2059:
2053:
2049:
2045:
2038:
1971:
1963:
1952:
1948:
1944:
1940:
1936:
1932:
1928:
1924:
1920:
1910:
1906:
1891:
1887:
1883:
1879:
1875:
1857:
1853:
1849:
1845:
1841:
1837:
1833:
1829:
1825:
1821:
1811:phenyl benzoate
1795:
1791:
1787:
1784:OH + NaOH → C
1783:
1779:
1775:
1701:
1697:
1653:
1639:Phenoxides are
1606:
1593:
1590:diethyl sulfide
1570:
1562:
1546:
1497:
1493:
1489:
1485:
1481:
1466:
1462:
1458:
1449:
1429:
1419:, and numerous
1349:
1342:
1338:
1334:
1315:
1311:
1307:
1284:(also known as
1279:
1272:
1267:
1266:
1265: ?)
1256:
1252:
1248:
1244:
1233:
1217:
1190:
1186:
1176:
1170:
1166:
1159:
1155:
1148:
1135:
1131:
1127:
1107:
1101:
1094:
1087:
1080:
1074:
1065:
1059:
1052:
1045:
1038:
1032:
1023:
1017:
1010:
1003:
997:
960:
959:
958:
957:
950:
943:
936:
932:
924:
885:
851:
837:
811:
744:
725:
721:
709:
704:
683:
677:18.0 (in DMSO),
667:
650:
646:
619:
615:
611:
579:
547:
534:
528:
520:
506:
503:
498:
497:
486:
483:
482:
476:
475:
472:
466:
465:
454:
436:
429:
419:
417:
416:2821 (solution)
406:
386:
370:
357:
345:
306:
286:
266:
246:
226:
213:
202:
189:
175:
174:
143:
142:
131:
130:
46:
43:carboxylic acid
35:
28:
23:
22:
15:
12:
11:
5:
5702:
5692:
5691:
5686:
5681:
5676:
5671:
5666:
5661:
5644:
5643:
5641:
5640:
5634:
5632:
5628:
5627:
5625:
5624:
5619:
5614:
5609:
5603:
5601:
5595:
5594:
5592:
5591:
5586:
5581:
5576:
5571:
5565:
5563:
5557:
5556:
5554:
5553:
5548:
5543:
5538:
5533:
5528:
5523:
5518:
5513:
5508:
5506:Chlorquinaldol
5503:
5498:
5493:
5479:
5474:
5469:
5467:Amylmetacresol
5464:
5459:
5453:
5451:
5445:
5444:
5438:preparations (
5432:
5431:
5424:
5417:
5409:
5400:
5399:
5396:
5395:
5394:
5393:
5390:
5379:
5373:
5367:
5366:
5363:
5362:
5360:
5359:
5354:
5349:
5344:
5339:
5334:
5329:
5324:
5318:
5316:
5312:
5311:
5309:
5308:
5303:
5298:
5292:
5290:
5284:
5283:
5281:
5280:
5278:Silver nitrate
5274:
5272:
5265:
5264:
5262:
5261:
5256:
5251:
5246:
5241:
5236:
5231:
5225:
5223:
5216:
5215:
5213:
5212:
5207:
5202:
5197:
5192:
5178:
5173:
5167:
5165:
5159:
5158:
5156:
5155:
5150:
5145:
5143:Chlorquinaldol
5140:
5134:
5132:
5125:
5124:
5122:
5121:
5116:
5111:
5105:
5103:
5096:
5095:
5093:
5092:
5086:
5084:
5077:
5076:
5074:
5073:
5068:
5063:
5058:
5053:
5048:
5043:
5038:
5032:
5030:
5023:
5022:
5020:
5019:
5014:
5009:
5004:
4999:
4993:
4991:
4981:
4980:
4978:
4977:
4972:
4967:
4961:
4959:
4952:
4951:
4935:
4934:
4927:
4920:
4912:
4906:
4905:
4900:
4895:
4890:
4885:
4880:
4875:
4868:
4867:External links
4865:
4863:
4862:
4835:(1): 199–206.
4818:
4799:(11): 1303–7.
4780:
4745:
4719:
4676:
4654:
4642:
4615:Anesthesiology
4601:
4566:
4544:
4517:(8): 695–701.
4497:
4452:
4422:
4396:
4383:
4370:
4327:
4324:on 2006-11-12.
4305:
4284:
4270:
4246:
4239:
4221:
4214:
4193:
4186:
4168:
4153:
4133:
4116:
4095:
4063:
4039:
4009:
4000:"Phenol spray"
3991:
3966:
3941:
3917:
3893:
3861:
3855:978-3527306732
3854:
3826:
3799:
3761:
3749:
3740:
3705:
3678:
3647:
3619:
3595:
3578:
3571:
3545:
3539:978-3527306732
3538:
3510:
3466:
3459:
3433:
3406:
3399:
3387:Wothers, Peter
3383:Warren, Stuart
3370:
3342:
3310:
3301:
3292:
3273:
3267:
3243:
3236:
3210:
3204:978-3527306732
3203:
3166:
3139:
3118:
3085:
3066:(7): 2607–20.
3049:
3021:
3007:
3000:
2996:
2989:
2958:
2956:
2953:
2952:
2951:
2946:
2941:
2936:
2931:
2924:
2921:
2913:hydroxyl group
2897:Main article:
2894:
2891:
2859:Chemical burns
2850:
2792:
2789:
2765:
2764:Biodegradation
2762:
2731:4-methylphenol
2723:temporal gland
2718:
2715:
2683:
2680:
2668:
2667:
2653:
2652:
2626:Meanwhile, in
2568:
2565:
2520:
2517:
2509:European Union
2488:for obtaining
2469:but also many
2416:polycarbonates
2403:
2400:
2396:Salicylic acid
2393:
2392:
2385:
2380:
2376:
2372:
2368:
2364:
2360:
2356:
2352:
2332:
2329:
2321:Lummus process
2312:
2311:Coal pyrolysis
2309:
2305:
2304:
2299:
2295:
2291:
2287:
2283:
2279:
2274:
2270:
2266:
2262:
2242:
2239:
2238:
2237:
2232:
2228:
2224:
2220:
2216:
2212:
2208:
2204:
2179:
2176:
2171:
2168:
2150:
2149:
2144:
2140:
2136:
2132:
2128:
2124:
2120:
2116:
2085:
2079:
2078:
2073:
2069:
2065:
2061:
2051:
2047:
2037:
2034:
1989:, also called
1987:cumene process
1970:
1969:Cumene process
1967:
1962:
1959:
1955:
1954:
1950:
1946:
1942:
1938:
1934:
1930:
1926:
1922:
1908:
1895:
1894:
1889:
1885:
1881:
1877:
1861:
1860:
1855:
1851:
1847:
1843:
1839:
1835:
1831:
1827:
1823:
1799:
1798:
1793:
1789:
1785:
1781:
1777:
1769:carbon dioxide
1740:(e.g. certain
1731:hydroperoxides
1723:cyclohexanones
1699:
1652:
1649:
1643:stabilised by
1605:
1602:
1578:hydrogen bonds
1569:
1566:
1560:
1544:
1528:ortho and para
1516:
1515:
1501:
1500:
1495:
1491:
1487:
1483:
1464:
1460:
1448:
1445:
1428:
1425:
1389:polycarbonates
1358:chemical burns
1344:) bonded to a
1340:
1336:
1313:
1309:
1277:
1274:
1273:
1268:
1246:
1245:
1241:standard state
1238:
1235:
1234:
1232:
1231:
1226:
1220:
1218:
1215:
1212:
1211:
1207:
1206:
1202:
1195:
1194:
1187:
1181:
1178:
1177:
1175:
1174:
1163:
1151:
1149:
1143:
1140:
1139:
1128:
1122:
1119:
1118:
1109:
1108:
1106:
1105:
1098:
1091:
1083:
1081:
1072:
1070:
1067:
1066:
1064:
1063:
1056:
1049:
1041:
1039:
1030:
1028:
1025:
1024:
1022:
1021:
1014:
1006:
1004:
995:
993:
990:
989:
982:
981:
978:
972:
971:
968:
962:
961:
951:
944:
937:
922:
921:
920:
919:
917:
908:
907:
901:P305+P351+P338
886:
881:
878:
877:
852:
847:
844:
843:
838:
833:
830:
829:
812:
807:
804:
803:
793:
792:
788:
787:
745:
740:
737:
736:
732:
731:
722:
717:
714:
713:
706:
702:
695:
694:
691:
689:Conjugate base
685:
684:
682:
681:
678:
675:
671:
669:
665:
655:
654:
643:
641:Vapor pressure
637:
636:
633:
624:
623:
612:
607:
604:
603:
600:
594:
593:
590:
584:
583:
576:
570:
569:
566:
560:
559:
556:
552:
551:
545:
539:
538:
532:
526:
521:
516:
513:
512:
508:
507:
505:
504:
501:
493:
492:
491:
488:
487:
485:
484:
480:
479:
477:
473:
470:
469:
461:
460:
459:
456:
455:
453:
452:
439:
437:
425:
422:
421:
414:
408:
407:
405:
404:
396:
394:
388:
387:
385:
384:
380:
378:
372:
371:
369:
368:
360:
358:
350:
347:
346:
344:
343:
335:
333:
327:
326:
316:
308:
307:
305:
304:
296:
294:
288:
287:
285:
284:
276:
274:
268:
267:
265:
264:
256:
254:
248:
247:
245:
244:
236:
234:
228:
227:
225:
224:
216:
214:
207:
204:
203:
201:
200:
192:
190:
185:
182:
181:
177:
176:
173:
172:
169:
168:Phenyl alcohol
166:
163:
162:Hydroxybenzene
160:
157:
154:
150:
149:
145:
144:
140:
139:
133:
132:
128:
127:
121:
120:
116:
115:
107:
106:
103:
102:
93:
79:
78:
75:
74:
65:
26:
9:
6:
4:
3:
2:
5701:
5690:
5687:
5685:
5682:
5680:
5677:
5675:
5672:
5670:
5667:
5665:
5662:
5660:
5657:
5656:
5654:
5639:
5636:
5635:
5633:
5629:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5604:
5602:
5600:
5596:
5590:
5587:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5566:
5564:
5562:
5558:
5552:
5549:
5547:
5544:
5542:
5539:
5537:
5534:
5532:
5529:
5527:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5507:
5504:
5502:
5501:Chlorhexidine
5499:
5497:
5494:
5491:
5487:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5454:
5452:
5450:
5446:
5441:
5437:
5430:
5425:
5423:
5418:
5416:
5411:
5410:
5407:
5391:
5389:
5386:
5385:
5383:
5380:
5377:
5374:
5372:
5369:
5368:
5364:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5319:
5317:
5313:
5307:
5304:
5302:
5299:
5297:
5294:
5293:
5291:
5289:
5285:
5279:
5276:
5275:
5273:
5270:
5266:
5260:
5257:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5230:
5227:
5226:
5224:
5221:
5217:
5211:
5208:
5206:
5203:
5201:
5198:
5196:
5193:
5190:
5186:
5182:
5179:
5177:
5174:
5172:
5169:
5168:
5166:
5164:
5160:
5154:
5151:
5149:
5146:
5144:
5141:
5139:
5136:
5135:
5133:
5130:
5126:
5120:
5117:
5115:
5112:
5110:
5107:
5106:
5104:
5101:
5097:
5091:
5090:Nitrofurazone
5088:
5087:
5085:
5082:
5078:
5072:
5069:
5067:
5064:
5062:
5061:Chloroxylenol
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5033:
5031:
5028:
5024:
5018:
5015:
5013:
5010:
5008:
5005:
5003:
5002:Chlorhexidine
5000:
4998:
4995:
4994:
4992:
4990:
4986:
4982:
4976:
4973:
4971:
4968:
4966:
4963:
4962:
4960:
4957:
4953:
4948:
4944:
4943:disinfectants
4940:
4933:
4928:
4926:
4921:
4919:
4914:
4913:
4910:
4904:
4901:
4899:
4896:
4894:
4891:
4889:
4886:
4884:
4881:
4879:
4876:
4874:
4871:
4870:
4858:
4854:
4850:
4846:
4842:
4838:
4834:
4830:
4822:
4814:
4810:
4806:
4802:
4798:
4794:
4793:
4784:
4776:
4772:
4768:
4764:
4760:
4756:
4749:
4733:
4729:
4723:
4715:
4711:
4707:
4703:
4699:
4695:
4691:
4687:
4680:
4672:
4665:
4658:
4652:
4646:
4638:
4634:
4629:
4624:
4620:
4616:
4612:
4605:
4597:
4593:
4589:
4585:
4582:(4): 517–21.
4581:
4577:
4570:
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4551:
4549:
4540:
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4528:
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4435:Bruichladdich
4432:
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4409:
4403:
4401:
4393:
4387:
4380:
4374:
4366:
4362:
4358:
4354:
4350:
4346:
4343:(4): 539–49.
4342:
4338:
4331:
4323:
4319:
4315:
4309:
4302:
4298:
4295:
4294:
4288:
4281:
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4259:
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4255:
4253:
4251:
4242:
4240:9781407024530
4236:
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4215:9781407024530
4211:
4207:
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4187:9781407024530
4183:
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4001:
3995:
3981:
3980:www.canada.ca
3977:
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3955:www.canada.ca
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3720:
3716:
3709:
3701:
3697:
3693:
3689:
3682:
3668:on 2019-10-27
3667:
3663:
3656:
3654:
3652:
3637:on 2007-04-09
3636:
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3608:
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3535:
3531:
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3523:
3522:
3514:
3500:on 2011-06-05
3499:
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3358:
3355:
3354:
3353:Can. J. Chem.
3346:
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3333:
3329:
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3314:
3305:
3296:
3290:
3289:0-534-07968-7
3286:
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3259:
3254:
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3237:9780470857274
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3065:
3061:
3053:
3045:
3041:
3034:
3032:
3030:
3028:
3026:
3017:
3016:"Phenol_msds"
3011:
3004:
2992:
2986:
2982:
2978:
2974:
2971:. Cambridge:
2970:
2963:
2959:
2950:
2947:
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2700:
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2679:
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2661:
2660:
2659:
2650:
2646:
2645:
2644:
2639:
2637:
2633:
2629:
2624:
2621:
2620:Louis Pasteur
2616:
2615:Joseph Lister
2612:
2607:
2605:
2601:
2597:
2593:
2589:
2585:
2578:
2573:
2564:
2562:
2558:
2554:
2549:
2545:
2541:
2536:
2534:
2530:
2529:carbolic soap
2526:
2516:
2514:
2510:
2506:
2501:
2499:
2495:
2491:
2490:nucleic acids
2487:
2483:
2480:
2479:liquid–liquid
2476:
2472:
2468:
2463:
2461:
2457:
2453:
2449:
2445:
2441:
2440:cyclohexanone
2437:
2436:hydrogenation
2433:
2429:
2425:
2421:
2417:
2413:
2409:
2399:
2397:
2390:
2386:
2349:
2348:
2347:
2345:
2337:
2328:
2326:
2322:
2318:
2308:
2280:
2259:
2258:
2257:
2255:
2251:
2247:
2246:Chlorobenzene
2201:
2200:
2199:
2197:
2193:
2189:
2185:
2175:
2170:Older methods
2167:
2165:
2164:cyclohexanone
2161:
2160:hydroperoxide
2157:
2153:
2113:
2112:
2111:
2109:
2105:
2100:
2098:
2094:
2089:
2083:
2082:Nitrous oxide
2058:
2057:
2056:
2043:
2033:
2031:
2027:
2026:cyclohexanone
2023:
2019:
2018:hydroperoxide
2015:
2011:
2006:
2004:
2000:
1996:
1992:
1988:
1980:
1975:
1966:
1958:
1919:
1918:
1917:
1915:
1904:
1900:
1884:OH + Zn → C
1874:
1873:
1872:
1870:
1866:
1820:
1819:
1818:
1816:
1812:
1808:
1804:
1774:
1773:
1772:
1770:
1766:
1762:
1758:
1757:carbonic acid
1754:
1749:
1747:
1743:
1739:
1736:
1732:
1728:
1724:
1720:
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1637:
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1619:
1610:
1601:
1599:
1591:
1587:
1586:diethyl ether
1583:
1579:
1575:
1565:
1559:
1555:
1551:
1547:
1543:
1537:
1533:
1529:
1525:
1521:
1511:
1507:
1503:
1502:
1480:
1479:
1478:
1476:
1472:
1469:(also called
1457:
1454:
1444:
1442:
1438:
1434:
1424:
1422:
1418:
1414:
1410:
1406:
1402:
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1390:
1386:
1382:
1378:
1374:
1370:
1366:
1361:
1359:
1355:
1347:
1346:hydroxy group
1332:
1328:
1324:
1321:
1306:
1302:
1299:
1295:
1291:
1290:phenolic acid
1287:
1286:carbolic acid
1283:
1271:
1264:
1259:
1242:
1236:
1230:
1227:
1225:
1222:
1221:
1219:
1214:
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1203:
1200:
1197:
1196:
1188:
1184:
1180:
1179:
1164:
1153:
1152:
1150:
1147:(Recommended)
1146:
1142:
1141:
1129:
1126:(Permissible)
1125:
1121:
1120:
1116:
1115:
1110:
1099:
1092:
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1084:
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1078:
1069:
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784:
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749:
746:
743:
739:
738:
735:Pharmacology
733:
730:
723:
720:
719:Dipole moment
716:
715:
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690:
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598:Boiling point
596:
595:
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588:Melting point
586:
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467:
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457:
449:
445:
444:DTXSID5021124
441:
440:
438:
428:
424:
423:
420:1671 (solid)
418:2312 (molten)
415:
413:
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389:
382:
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353:
349:
348:
341:
337:
336:
334:
332:
329:
328:
324:
320:
317:
315:
313:ECHA InfoCard
310:
309:
302:
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293:
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282:
278:
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269:
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206:
205:
198:
194:
193:
191:
188:
184:
183:
178:
170:
167:
164:
161:
159:Phenylic acid
158:
156:Phenolic acid
155:
153:Carbolic acid
152:
151:
146:
138:
134:
126:
122:
117:
113:
108:
98:
94:
89:
85:
84:
80:
70:
66:
61:
57:
56:
52:
44:
40:
39:carbonic acid
33:
19:
18:Carbolic acid
5638:Flurbiprofen
5545:
5541:Oxyquinoline
5477:Benzethonium
5472:Benzalkonium
5171:Benzalkonium
5148:Oxyquinoline
5056:Triclocarban
5045:
5041:Policresulen
5026:
5017:Polihexanide
4832:
4828:
4821:
4796:
4790:
4783:
4758:
4754:
4748:
4736:. Retrieved
4731:
4722:
4692:(1): 61–72.
4689:
4685:
4679:
4670:
4657:
4645:
4621:(3): 366–7.
4618:
4614:
4604:
4579:
4575:
4569:
4556:
4514:
4510:
4506:
4500:
4473:
4469:
4463:
4455:
4443:. Retrieved
4439:the original
4434:
4425:
4414:. Retrieved
4386:
4373:
4340:
4336:
4330:
4322:the original
4317:
4308:
4292:
4287:
4278:
4273:
4264:
4230:
4224:
4205:
4177:
4171:
4156:
4148:
4147:, series 3,
4144:
4136:
4124:
4119:
4111:
4110:, series 3,
4107:
4098:
4090:
4086:
4079:
4075:
4066:
4055:. Retrieved
4051:
4042:
4030:. Retrieved
4026:the original
4012:
3994:
3983:. Retrieved
3979:
3969:
3958:. Retrieved
3954:
3944:
3933:. Retrieved
3930:ec.europa.eu
3929:
3920:
3909:. Retrieved
3906:ec.europa.eu
3905:
3896:
3884:. Retrieved
3877:the original
3864:
3835:
3829:
3812:
3808:
3802:
3777:
3773:
3743:
3718:
3714:
3708:
3691:
3687:
3681:
3670:. Retrieved
3666:the original
3639:. Retrieved
3635:the original
3611:. Retrieved
3609:. 2017-01-11
3588:
3581:
3554:
3548:
3519:
3513:
3502:. Retrieved
3498:the original
3485:
3479:
3469:
3442:
3436:
3419:
3415:
3409:
3390:
3373:
3356:
3351:
3345:
3323:
3319:
3313:
3304:
3295:
3280:
3276:
3257:
3253:March, Jerry
3246:
3219:
3213:
3184:
3156:
3109:. Retrieved
3063:
3059:
3052:
3010:
2994:
2968:
2962:
2904:
2902:
2857:
2845:
2794:
2782:
2768:
2767:
2743:
2720:
2696:
2689:Nazi Germany
2685:
2673:
2670:
2663:
2656:
2648:
2641:
2625:
2608:
2581:
2553:Chloraseptic
2537:
2533:matrixectomy
2522:
2502:
2464:
2460:ethoxylation
2452:alkylphenols
2424:formaldehyde
2408:Condensation
2405:
2394:
2363:+ HCl + NaNO
2342:
2325:benzoic acid
2314:
2306:
2252:) or steam (
2244:
2181:
2173:
2166:and phenol.
2156:Autoxidation
2154:
2151:
2108:Dow Chemical
2101:
2090:
2080:
2039:
2007:
1991:Hock process
1990:
1984:
1979:autoxidation
1964:
1956:
1899:diazomethane
1896:
1862:
1800:
1767:to liberate
1750:
1694:
1682:halogenation
1671:
1638:
1627:
1615:
1571:
1557:
1541:
1517:
1474:
1470:
1452:
1450:
1430:
1362:
1331:phenyl group
1293:
1289:
1285:
1281:
1280:
1113:
1090:ppm (mammal)
985:
912:
840:
797:
662:
629:
376:RTECS number
180:Identifiers
148:Other names
5659:Antiseptics
5589:Tyrothricin
5574:Fusafungine
5561:Antibiotics
5511:Dequalinium
5482:Cetrimonium
5449:Antiseptics
5378:from market
5249:Nitromersol
5181:Cetrimonium
5138:Dequalinium
5131:derivatives
5083:derivatives
5007:Propamidine
4958:derivatives
4939:Antiseptics
4032:18 February
3422:(5): 1781.
3326:: 612–613.
2834:hydrophobic
2806:dysrhythmia
2717:Occurrences
2691:during the
2548:tympanotomy
2544:myringotomy
2456:nonylphenol
2446:. Nonionic
2412:bisphenol-A
2250:Dow process
1830:COCl + HOC
1690:sulfonation
1678:pi electron
1645:aromaticity
1604:Tautomerism
1385:derivatives
1320:crystalline
1104:ppm (mouse)
1000:median dose
986:Lethal dose
966:Flash point
835:Signal word
555:Appearance
511:Properties
319:100.003.303
261:ChEMBL14060
241:CHEBI:15882
165:Phenic acid
5653:Categories
5607:Benzocaine
5579:Gramicidin
5569:Bacitracin
5526:Hexetidine
5521:Hexamidine
5337:Monalazone
5254:Thiomersal
5153:Clioquinol
5081:Nitrofuran
5066:Biphenylol
5012:Hexamidine
4985:Biguanides
4761:(1): 1–6.
4416:2008-05-27
4263:"Phenol".
4093:: 308-328.
4057:2024-05-30
3985:2018-07-06
3960:2018-07-06
3935:2018-07-06
3911:2018-07-06
3672:2018-01-02
3641:2007-04-09
3613:2018-01-02
3572:0471497371
3504:2010-03-31
3460:0471497371
2955:References
2949:Polyphenol
2879:chloroform
2798:dermatitis
2711:a stranger
2611:antiseptic
2525:antiseptic
2471:herbicides
2448:detergents
2434:. Partial
2095:employing
1981:of cumene.
1961:Production
1809:solution,
1735:solid acid
1630:resorcinol
1427:Properties
1413:herbicides
1409:detergents
1397:explosives
1352:). Mildly
1224:Thiophenol
809:Pictograms
693:Phenoxide
543:Molar mass
401:339NCG44TV
272:ChemSpider
208:3D model (
187:CAS Number
5622:Lidocaine
5617:Dyclonine
5388:Phase III
5376:Withdrawn
5271:compounds
5244:Merbromin
5220:Mercurial
5200:Cetrimide
5129:Quinoline
5071:Fenticlor
5051:Triclosan
4975:Euflavine
4004:drugs.com
3886:25 August
3338:ECW model
2903:The word
2739:castoreum
2727:elephants
2707:Auschwitz
2698:Aktion T4
2636:cesspools
2277:OH + NaCl
2068:+ O → C
1995:oxidation
1738:catalysts
1686:acylation
1651:Reactions
1634:naphthols
1598:hard acid
1532:induction
1524:phenolate
1475:carbolate
1471:phenoxide
1453:phenolate
1377:precursor
1373:commodity
1369:petroleum
1097:ppm (rat)
980:1.8–8.6%
897:P301+P310
800:labelling
502:Oc1ccccc1
412:UN number
383:SJ3325000
5674:Oxoacids
5584:Neomycin
5490:chloride
5462:Ambazone
5332:Halazone
5288:Alcohols
5222:products
5189:chloride
5102:products
4989:amidines
4956:Acridine
4738:8 August
4714:10903419
4596:16621299
4539:16261859
4492:15653882
4445:8 August
4365:21368454
4357:10549891
4297:Archived
3794:99294625
3735:22684819
3389:(2001).
3255:(2007),
3163:(NIOSH).
3153:"Phenol"
3105:"Phenol"
3080:18324831
3046:(NIOSH).
2923:See also
2909:aromatic
2875:hospital
2841:radicals
2838:phenoxyl
2810:seizures
2791:Toxicity
2775:benzoate
2628:Carlisle
2588:coal tar
2454:, e.g.,
2432:Bakelite
2383:O + NaCl
2302:OH + HCl
2188:Monsanto
2014:oxidized
2012:. It is
1727:Alcohols
1641:enolates
1582:pyridine
1490:OH ⇌ C
1415:such as
1401:Bakelite
1381:plastics
1365:coal tar
1327:volatile
1325:that is
1298:aromatic
1296:) is an
1294:benzenol
913:NFPA 704
791:Hazards
742:ATC code
649:mmHg (20
292:DrugBank
197:108-95-2
141:Benzenol
5612:Cocaine
5486:bromide
5185:bromide
4837:Bibcode
4813:1416322
4775:1109265
4694:Bibcode
4637:2579602
4519:Bibcode
4379:article
3774:Synlett
3488:: 115.
3111:12 June
3040:"#0493"
2899:Phenols
2893:Phenols
2826:kidneys
2818:kidneys
2733:during
2666:, p. 63
2651:, p. 62
2567:History
2555:spray,
2540:otology
2519:Medical
2467:aspirin
2420:epoxide
2294:O → C
2223:OH + Na
2139:OH + CO
2104:toluene
2042:benzene
1929:OH + CH
1914:anisole
1865:benzene
1792:ONa + H
1746:Cresols
1742:zeolite
1721:), and
1554:acetone
1548:of the
1447:Acidity
1433:soluble
1393:epoxies
1305:formula
1263:what is
1261: (
1173:mg/m)
1169:ppm (60
1158:ppm (19
1138:mg/m)
1134:ppm (19
780: (
778:R02AA19
770: (
768:N01BX03
760: (
758:D08AE03
756:)
750: (
748:C05BB05
659:Acidity
574:Density
352:PubChem
301:DB03255
49:Phenol
32:Phenols
5546:Phenol
5436:Throat
5371:WHO-EM
5269:Silver
5100:Iodine
5046:Phenol
5027:Phenol
4857:625760
4855:
4811:
4773:
4712:
4635:
4594:
4537:
4490:
4363:
4355:
4237:
4212:
4184:
4022:Carmex
3852:
3792:
3733:
3569:
3536:
3457:
3397:
3287:
3265:
3234:
3201:
3135:Phenol
3078:
2987:
2939:Cresol
2905:phenol
2830:cancer
2816:. The
2812:, and
2758:whisky
2754:barley
2600:phenyl
2561:Carmex
2513:Canada
2426:gives
2375:OH + N
2290:Cl + H
2030:nylons
1999:cumene
1588:, and
1354:acidic
1282:Phenol
1258:verify
1255:
1201:(SDS)
1191:
1171:
1167:
1165:C 15.6
1160:
1156:
1136:
1132:
1102:
1095:
1088:
1060:
1053:
1046:
1018:
1011:
841:Danger
726:
710:
708:270.75
699:UV-vis
651:
647:
620:
616:
580:
548:94.113
495:SMILES
340:D00033
252:ChEMBL
129:Phenol
119:Names
5631:Other
5347:Eosin
5315:Other
4673:: 24.
4667:(PDF)
4561:Merck
4411:(PDF)
4361:S2CID
4129:p. 44
3880:(PDF)
3873:(PDF)
3790:S2CID
2861:from
2822:liver
2802:edema
2735:musth
2444:nylon
2184:Bayer
2127:+ 2 O
2016:to a
1892:+ ZnO
1858:+ HCl
1660:blue.
1498:O + H
1456:anion
1405:nylon
1375:as a
1323:solid
1292:, or
1162:mg/m)
1154:TWA 5
1130:TWA 5
1114:NIOSH
724:1.224
635:1.48
582:g/cm
463:InChI
232:ChEBI
210:JSmol
4987:and
4941:and
4853:PMID
4809:PMID
4771:PMID
4740:2015
4710:PMID
4633:PMID
4592:PMID
4535:PMID
4488:PMID
4447:2015
4353:PMID
4235:ISBN
4210:ISBN
4182:ISBN
4034:2015
3888:2015
3850:ISBN
3731:PMID
3567:ISBN
3534:ISBN
3455:ISBN
3395:ISBN
3285:ISBN
3263:ISBN
3232:ISBN
3199:ISBN
3113:2023
3076:PMID
2985:ISBN
2885:and
2863:skin
2824:and
2814:coma
2609:The
2559:and
2546:and
2511:and
2473:and
2418:and
2402:Uses
2367:→ C
2317:coal
2186:and
2131:→ C
1937:→ C
1869:zinc
1838:→ C
1744:).
1729:and
1698:PhOH
1550:enol
1193:ppm
1183:IDLH
905:P310
893:P280
889:P261
875:H373
871:H341
867:H331
863:H314
859:H311
855:H301
653:°C)
628:log
622:°C)
578:1.07
564:Odor
392:UNII
331:KEGG
5440:R02
4947:D08
4845:doi
4801:doi
4763:doi
4702:doi
4690:127
4623:doi
4584:doi
4527:doi
4478:doi
4345:doi
3842:doi
3817:doi
3782:doi
3723:doi
3696:doi
3692:100
3559:doi
3526:doi
3490:doi
3447:doi
3424:doi
3361:doi
3328:doi
3224:doi
3191:doi
3068:doi
2977:doi
2887:RNA
2883:DNA
2855:g.
2750:ppm
2557:TCP
2498:RNA
2496:or
2494:DNA
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2256:):
2231:+ H
2143:+ H
2091:An
1997:of
1949:+ N
1945:OCH
1912:),
1763:or
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1594:−OH
1572:In
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1473:or
1350:−OH
1189:250
1145:REL
1124:PEL
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1044:420
1016:270
1009:317
798:GHS
783:WHO
776:),
773:WHO
766:),
763:WHO
753:WHO
712:nm
703:max
645:0.4
614:8.3
432:EPA
365:996
355:CID
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