526:
1592:
281:
206:
567:
60:
2821:
1574:
4910:
2785:
50:
1583:
2809:
2797:
417:
590:
and therefore has a high activation barrier and is not a significant pathway at or near room temperature. However, even trace amounts of acids or bases (including water) can catalyze the reaction. Even with rigorous precautions to minimize adventitious moisture or proton sources, vinyl alcohol can
598:
The tautomerization can also be catalyzed via photochemical process. These findings suggest that the keto–enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere.
844:
barrier to the rearrangement being insurmountable at temperatures present in interstellar space. The vinyl alcohol to acetaldehyde rearrangement is the only keto-enol tautomerisation to have been detected in deep space, induced by the provision of secondary electrons from
1037:
Andrews, D. U.; Heazlewood, B. R.; Maccarone, A. T.; Conroy, T.; Payne, R. J.; Jordan, M. J. T.; Kable, S. H. (2012). "Photo-tautomerization of acetaldehyde to vinyl alcohol: A potential route to tropospheric acids".
1091:
Cederstav, Anna K.; Novak, Bruce M. (1994). "Investigations into the
Chemistry of Thermodynamically Unstable Species. The Direct Polymerization of Vinyl Alcohol, the Enolic Tautomer of Acetaldehyde".
988:
Heazlewood, B. R.; Maccarone, A. T.; Andrews, D. U.; Osborn, D. L.; Harding, L. B.; Klippenstein, S. J.; Jordan, M. J. T.; Kable, S. H. (2011). "Near-threshold H/D exchange in CD
2134:
1904:
1864:
1356:
2065:
2040:
2030:
2882:
3573:
3563:
3558:
2436:
1764:
1705:
1613:
4272:
3815:
3583:
3578:
3568:
3501:
3491:
3485:
2525:
2341:
2276:
2216:
2144:
2050:
1944:
1814:
1769:
1440:
2605:
3830:
3820:
3553:
3543:
3511:
3506:
3496:
2070:
1914:
1884:
4257:
3708:
3548:
3480:
3469:
2000:
1980:
1653:
2025:
430:
3538:
1122:
4511:
4252:
3414:
1663:
1365:
2020:
1349:
4944:
4516:
4506:
3403:
1690:
2236:
1633:
1784:
337:
1695:
1342:
2563:
1879:
1160:
1093:
602:
Vinyl alcohol can be stabilized by controlling the water concentration in the system and utilizing the kinetic favorability of the
595:
is another example of a substance that is stable when rigorously pure, but decomposes rapidly due to catalysis by trace moisture.)
2095:
1854:
1774:
915:
884:
2476:
1192:
425:
2858:
2728:
1139:
4861:
4661:
2628:
1158:; Francis, J. N.; Frenz, B. A.; Tsutsui, M. (1973). "Structure of a dihapto(vinyl alcohol) complex of platinum(II)".
295:
437:
4890:
2753:
548:) by 42.7 kJ/mol. Vinyl alcohol gas isomerizes to the aldehyde with a half-life of 30 min at room temperature.
952:
Keith, J. A.; Henry, P. M. (2009). "The
Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations".
4756:
3850:
3793:
2678:
2713:
238:
201:
59:
4804:
3156:
3028:
1909:
874:
587:
259:
163:
4866:
4165:
3096:
3091:
658:
O). Studies show that the tautomerization process is significantly inhibited at ambient temperatures (
4885:
4876:
4856:
3086:
2668:
2663:
1844:
1235:
583:
4939:
4210:
2708:
488:
immediately upon isolation near room temperature. It is not a practical precursor to any compound.
276:
49:
4741:
4107:
2788:
907:
17:
4746:
3131:
3081:
3076:
2851:
2643:
1608:
1518:
1395:
1390:
607:
525:
4781:
4170:
2698:
2673:
2311:
1929:
1476:
954:
4871:
3168:
3141:
2759:
2743:
2368:
1739:
1710:
1591:
1415:
1049:
1003:
846:
772:
497:
247:
183:
79:
8:
4895:
4247:
4190:
4152:
3825:
3810:
3788:
3136:
3048:
2948:
2867:
2703:
2683:
2496:
2186:
1674:
1538:
1513:
1481:
1400:
833:
143:
119:
109:
1053:
1007:
280:
205:
4809:
4790:
4666:
4282:
4127:
4122:
4117:
4112:
3867:
3733:
3199:
3038:
2930:
2897:
2801:
2723:
2693:
2638:
2515:
2491:
1990:
1924:
1789:
1749:
1600:
1563:
1523:
1502:
1445:
1420:
1320:
1073:
1267:
Kleimeier, N. Fabian; Kaiser, Ralf I. (2021). "Interstellar
Enolization-Acetaldehyde (
4913:
4844:
4765:
4277:
3880:
3859:
3835:
3783:
3778:
3681:
3661:
3651:
3641:
3636:
3121:
3053:
2989:
2922:
2917:
2844:
2748:
2331:
2231:
2201:
2119:
1859:
1744:
1700:
1648:
1455:
1450:
1382:
1324:
1312:
1135:
1065:
1040:
1019:
970:
911:
880:
841:
688:
4785:
1334:
1077:
4314:
4262:
4205:
4032:
3979:
3875:
3773:
3676:
3646:
3626:
3616:
3474:
3126:
2825:
2813:
2733:
2633:
2538:
2486:
1919:
1794:
1759:
1680:
1668:
1628:
1533:
1466:
1304:
1244:
1169:
1155:
1127:
1102:
1057:
1011:
994:
962:
899:
465:
360:
227:
4849:
4818:
4751:
4718:
4671:
4656:
4324:
4018:
4013:
3974:
3698:
3666:
3631:
3181:
3116:
3111:
3106:
3101:
3043:
3008:
2907:
2421:
2396:
1934:
1874:
1658:
1558:
1543:
1528:
1435:
1425:
796:
501:
4934:
4880:
4795:
4651:
4200:
4160:
3845:
3621:
3611:
3606:
3596:
3463:
3425:
3408:
3392:
3348:
3337:
3331:
3176:
3071:
2961:
2658:
2623:
2406:
2296:
2261:
2246:
2181:
2176:
2075:
1975:
1894:
1869:
1834:
1779:
1754:
1623:
1471:
829:
799:
575:
408:
566:
4928:
4834:
4733:
4292:
4267:
4239:
4182:
4005:
3953:
3840:
3768:
3763:
3601:
3436:
3430:
3419:
3359:
3353:
3342:
3033:
2981:
2956:
2688:
2543:
2426:
2401:
2382:
2326:
2164:
2159:
1899:
1889:
1849:
1724:
1618:
1573:
1548:
1430:
1410:
1131:
692:
685:
592:
399:
194:
1061:
4723:
4099:
3758:
3326:
3151:
2764:
2618:
2471:
2411:
2391:
2363:
2291:
2171:
2154:
2109:
2060:
1965:
1685:
1638:
1486:
1316:
1308:
1295:
1069:
1023:
974:
966:
837:
646:= 12). Deuterium stabilization can be accomplished through hydrolysis of a
591:
only be stored for minutes to hours before it isomerizes to acetaldehyde. (
571:
517:
485:
1188:
4839:
4813:
4703:
4550:
4142:
4137:
4132:
3923:
3397:
3320:
3314:
2738:
2648:
2613:
2580:
2506:
2481:
2321:
2226:
2196:
2080:
1995:
1985:
1715:
1643:
870:
651:
1173:
1106:
4800:
4713:
4708:
4613:
4414:
4344:
4220:
4042:
3943:
3753:
3748:
3718:
3713:
3671:
3386:
3269:
3259:
3249:
3204:
2938:
2912:
2892:
2653:
2595:
2558:
2533:
2431:
2241:
2104:
1189:"Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space"
1015:
696:
379:
174:
4608:
4598:
4580:
4434:
4225:
4080:
3933:
3743:
3738:
3728:
3723:
3703:
3308:
3280:
3274:
3264:
3254:
3209:
2585:
2450:
2286:
2090:
1970:
1824:
1799:
666:
603:
407:
Except where otherwise noted, data are given for materials in their
4687:
4603:
4575:
4560:
4555:
4496:
4491:
4475:
4404:
4394:
4364:
4354:
4334:
4070:
4066:
4046:
4028:
3995:
3903:
3239:
3020:
2994:
2553:
2465:
2266:
2129:
2114:
2085:
1954:
1729:
1553:
1497:
1491:
1460:
1405:
1373:
1249:
1217:
513:
507:
472:
142:
4565:
4545:
4501:
4457:
4384:
4374:
4215:
4195:
4056:
3913:
3244:
3191:
3146:
3063:
2969:
2902:
2718:
2548:
2501:
2460:
2416:
2358:
2353:
2316:
2306:
2301:
2256:
2251:
2191:
2124:
2015:
2010:
1960:
1839:
1829:
1582:
214:
32:
28:
1036:
987:
876:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
4631:
4424:
3656:
2769:
2590:
2572:
2035:
2005:
1507:
803:
776:
650:
precursor in the presence of a slight stoichiometric excess of
647:
479:
469:
154:
4570:
1804:
1734:
868:
700:
132:
264:
2836:
932:
879:(6th ed.), New York: Wiley-Interscience, p. 101,
578:) proceeds via the intermediacy of a vinyl alcohol complex.
461:
1154:
832:) to be detected in space. Its stability in the (dilute)
1120:
Hallensleben ML (2000). "Polyvinyl
Compounds, Others".
691:(PVA or PVOH) is made indirectly by polymerization of
679:
1364:
1218:"Microwave Detection of Interstellar Vinyl Alcohol,
898:
790:
1262:
1260:
676:= 42 minutes for first-order hydrolysis kinetics.
504:at a temperature of 900 °C and low pressure.
684:Because of the instability of vinyl alcohol, the
512:Under normal conditions, vinyl alcohol converts (
4926:
1257:
586:by a 1,3-hydrogen migration is forbidden by the
508:Tautomerization of vinyl alcohol to acetaldehyde
226:
1266:
836:shows that its tautomerization does not happen
118:
1123:Ullmann's Encyclopedia of Industrial Chemistry
1090:
2852:
1350:
496:Vinyl alcohol can be formed by the pyrolytic
1215:
1119:
930:
669:of the enol form can easily be increased to
484:, it is a labile compound that converts to
2859:
2845:
1357:
1343:
1211:
1209:
951:
775:are known that contain vinyl alcohol as a
279:
204:
182:
1248:
933:"CCCBDB NIST Standard Reference Database"
703:bonds (Ac = acetyl; HOAc = acetic acid):
246:
1161:Journal of the American Chemical Society
1094:Journal of the American Chemical Society
902:; Greeves, Nick; Warren, Stuart (2012).
565:
1206:
864:
862:
840:, a fact attributed to the size of the
275:
14:
4927:
1113:
945:
802:in 2001, the last of the three stable
195:
4945:Organic compounds with 2 carbon atoms
2840:
1338:
1216:Turner, B. E.; Apponi, A. J. (2001).
540:) is more stable than vinyl alcohol (
324:Key: IMROMDMJAWUWLK-UHFFFAOYSA-N
307:Key: IMROMDMJAWUWLK-UHFFFAOYSA-N
162:
4006:Polyhydric alcohols (sugar alcohols)
1193:National Radio Astronomy Observatory
1186:
859:
680:Relationship to poly(vinyl alcohol)
532:At room temperature, acetaldehyde (
217:
24:
2729:Nexus for Exoplanet System Science
795:Vinyl alcohol was detected in the
58:
48:
25:
4956:
4662:2-Methyl-2-propyl-1,3-propanediol
2629:Atomic and molecular astrophysics
1366:Molecules detected in outer space
1187:Blue, Charles (October 1, 2001).
791:Occurrence in interstellar medium
4909:
4908:
2819:
2807:
2795:
2784:
2783:
1590:
1581:
1572:
524:
415:
4891:Nucleophilic conjugate addition
2754:Polycyclic aromatic hydrocarbon
1180:
411:(at 25 °C , 100 kPa).
321:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
314:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
304:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
63:Ball-and-stick model of ethenol
1148:
1084:
1030:
981:
924:
892:
766:
13:
1:
4862:Fischer–Speier esterification
3794:Propylene glycol methyl ether
2679:Extraterrestrial liquid water
852:
779:. One example is Pt(acac)(η-C
456:(IUPAC name; not ethanol) or
53:Structural formula of ethenol
2866:
570:The industrial synthesis of
491:
7:
3029:4-Methylcyclohexanemethanol
1910:Protonated hydrogen cyanide
44:
10:
4961:
4867:Williamson ether synthesis
4166:2,4-Dichlorobenzyl alcohol
3097:2-(2-Methoxyethoxy)ethanol
3092:2-(2-Methoxyethoxy)ethanol
384:44.053 g/mol
26:
4904:
4886:Friedel-Crafts alkylation
4877:Nucleophilic substitution
4857:Nucleophilic substitution
4827:
4774:
4732:
4696:
4680:
4644:
4622:
4589:
4536:
4529:
4484:
4466:
4448:
4300:
4291:
4234:
4179:
4151:
4098:
4004:
3988:
3967:
3896:
3889:
3801:
3690:
3520:
3445:
3368:
3290:
3221:
3190:
3087:2-(2-Ethoxyethoxy)ethanol
3062:
3019:
3007:
2980:
2947:
2881:
2874:
2778:
2669:Earliest known life forms
2664:Diffuse interstellar band
2604:
2524:
2449:
2340:
2275:
2215:
2143:
2135:Protonated cyanoacetylene
2049:
1943:
1905:Protonated carbon dioxide
1865:Hydromagnesium isocyanide
1813:
1599:
1570:
1381:
1372:
1236:The Astrophysical Journal
405:
388:
353:
333:
291:
102:
90:
78:
73:
43:
4108:2,2-Dimethylpropan-1-ol
3164:-Diisopropylaminoethanol
2714:Iron–sulfur world theory
2709:Photodissociation region
2412:Methyl-cyano-diacetylene
1132:10.1002/14356007.a21_743
992:CHO photodissociation".
828:(after acetaldehyde and
27:Not to be confused with
4742:1,3-Difluoro-2-propanol
2789:Category:Astrochemistry
2379:, fullerene, buckyball)
2066:Cyanobutadiynyl radical
2041:Silicon-carbide cluster
2031:Protonated formaldehyde
1126:. Weinheim: Wiley-VCH.
1062:10.1126/science.1220712
908:Oxford University Press
588:Woodward–Hoffmann rules
4747:2,2,2-Trifluoroethanol
3132:Aminoethylethanolamine
3082:2,2,2-Trifluoroethanol
3077:2,2,2-Trichloroethanol
2802:Outer space portal
2644:Circumstellar envelope
1609:Aluminium(I) hydroxide
1519:Phosphorus mononitride
1396:Aluminium monofluoride
1391:Aluminium monochloride
1309:10.1002/cphc.202100111
967:10.1002/anie.200902194
608:kinetic isotope effect
579:
64:
54:
4171:3-Nitrobenzyl alcohol
2699:Interplanetary medium
2674:Extraterrestrial life
2312:Octatetraynyl radical
1930:Tricarbon monosulfide
1477:Magnesium monohydride
1280:) and Vinyl Alcohol (
955:Angew. Chem. Int. Ed.
584:keto–enol tautomerism
569:
62:
52:
4872:Elimination reaction
3574:1-Heptatetracontanol
3564:1-Pentatetracontanol
3559:1-Tetratetracontanol
3466:(melissyl / myricyl)
3433:(cluytyl / montanyl)
3142:Dimethylethanolamine
2826:Chemistry portal
2814:Astronomy portal
2760:RNA world hypothesis
2744:PAH world hypothesis
2437:Heptatrienyl radical
2369:Buckminsterfullerene
2257:Methylcyanoacetylene
1765:Silicon carbonitride
1740:Methylidynephosphane
1706:Magnesium isocyanide
1614:Aluminium isocyanide
1416:Carbon monophosphide
1293:) as a Case Study".
847:galactic cosmic rays
80:Preferred IUPAC name
4896:Transesterification
4273:Palmitoleyl alcohol
4248:3-Methyl-3-pentanol
4191:Cetostearyl alcohol
4128:3-Methylbutan-2-ol
4123:3-Methylbutan-1-ol
4118:2-Methylbutan-2-ol
4113:2-Methylbutan-1-ol
3897:Monohydric alcohols
3826:3-Methyl-3-pentanol
3816:2-Methylheptan-2-ol
3811:2-Methyl-2-pentanol
3584:1-Nonatetracontanol
3579:1-Octatetracontanol
3569:1-Hexatetracontanol
3502:1-Heptatriacontanol
3492:1-Pentatriacontanol
3486:1-Tetratriacontanol
3172:-Methylethanolamine
3137:Diethylethanolamine
3049:Methylazoxymethanol
2966:Methanol poisoning
2704:Interstellar medium
2684:Forbidden mechanism
2497:Hydrogen isocyanide
2187:Hexatriynyl radical
1770:c-Silicon dicarbide
1675:Hydrogen isocyanide
1539:Silicon monosulfide
1514:Phosphorus monoxide
1482:Methylidyne radical
1441:Fluoromethylidynium
1401:Aluminium(II) oxide
1174:10.1021/ja00789a011
1107:10.1021/ja00088a051
1054:2012Sci...337.1203A
1048:(6099): 1203–1206.
1008:2011NatCh...3..443H
910:. pp. 456–57.
869:Smith, Michael B.;
834:interstellar medium
665:≈ 10 M/s), and the
40:
4791:Carbonyl reduction
4667:Diethylpropanediol
4283:tert-Butyl alcohol
3989:Trihydric alcohols
3831:3-Methyloctan-3-ol
3821:2-Methylhexan-2-ol
3734:3-Methyl-2-butanol
3554:1-Tritetracontanol
3544:1-Hentetracontanol
3512:1-Nonatriacontanol
3507:1-Octatriacontanol
3497:1-Hexatriacontanol
3345:(cetyl / palmityl)
3200:2-Methyl-1-butanol
3039:Cyclohexylmethanol
2898:2-Methyl-1-butanol
2724:Molecules in stars
2694:Intergalactic dust
2639:Circumstellar dust
2581:Naphthalene cation
2516:Trihydrogen cation
2492:Hydrogen deuteride
2417:Methyltriacetylene
2252:Hexapentaenylidene
2071:E-Cyanomethanimine
1991:Cyclopropenylidene
1925:Tricarbon monoxide
1915:Silicon tricarbide
1885:Methylene amidogen
1875:Isothiocyanic acid
1790:Thioxoethenylidene
1750:Trihydrogen cation
1564:Titanium(II) oxide
1524:Potassium chloride
1503:Sulfur mononitride
1446:Helium hydride ion
1421:Carbon monosulfide
1016:10.1038/nchem.1052
931:R.D. Johnson III.
580:
460:, is the simplest
438:Infobox references
389:Related compounds
65:
55:
38:
4922:
4921:
4845:Alcohol oxidation
4766:Trifluoromethanol
4640:
4639:
4525:
4524:
4278:tert-Amyl alcohol
4258:Linolenyl alcohol
4153:Aromatic alcohols
4094:
4093:
3968:Dihydric alcohols
3881:Triphenylmethanol
3836:Diacetone alcohol
3784:Pinacolyl alcohol
3709:2-Deoxyerythritol
3682:Veratrole alcohol
3662:Propargyl alcohol
3652:Phenethyl alcohol
3642:Nicotinyl alcohol
3637:Neopentyl alcohol
3592:
3591:
3549:1-Dotetracontanol
3481:1-Tritriacontanol
3470:1-Hentriacontanol
3122:2-Mercaptoethanol
3054:Trifluoromethanol
3003:
3002:
2990:Isopropyl alcohol
2918:Phenethyl alcohol
2883:Alcohols found in
2834:
2833:
2749:Pseudo-panspermia
2445:
2444:
2392:Cyanodecapentayne
2332:N-Methylformamide
2307:Methyldiacetylene
2232:Aminoacetonitrile
2202:Methyl isocyanate
2120:Methyl isocyanide
2001:Isocyanoacetylene
1981:Cyanoformaldehyde
1860:Hydrogen peroxide
1745:Potassium cyanide
1701:Magnesium cyanide
1654:Disilicon carbide
1649:Dicarbon monoxide
1456:Hydrogen fluoride
1451:Hydrogen chloride
1303:(12): 1229–1236.
1191:(Press release).
961:(48): 9038–9049.
917:978-0-19-927029-3
904:Organic Chemistry
900:Clayden, Jonathan
886:978-0-471-72091-1
842:activation energy
689:polyvinyl alcohol
446:Chemical compound
444:
443:
395:Related compounds
260:CompTox Dashboard
144:Interactive image
69:
68:
16:(Redirected from
4952:
4912:
4911:
4534:
4533:
4530:Terpene alcohols
4315:Methylene glycol
4298:
4297:
4263:Linoleyl alcohol
4206:Myristyl alcohol
4033:Propylene glycol
3980:Propylene glycol
3894:
3893:
3876:Triphenylethanol
3789:Pirkle's alcohol
3774:Diphenylmethanol
3677:Vanillyl alcohol
3647:Perillyl alcohol
3627:Furfuryl alcohol
3617:Cinnamyl alcohol
3475:1-Dotriacontanol
3127:2-Methoxyethanol
3017:
3016:
2885:alcoholic drinks
2879:
2878:
2861:
2854:
2847:
2838:
2837:
2824:
2823:
2822:
2812:
2811:
2810:
2800:
2799:
2798:
2787:
2786:
2734:Organic compound
2634:Chemical formula
2539:Dihydroxyacetone
2487:Hydrogen cyanide
2172:Cyanodiacetylene
2026:Propadienylidene
1920:Thioformaldehyde
1795:Titanium dioxide
1760:Sodium hydroxide
1681:Hydrogen sulfide
1669:Hydrogen cyanide
1629:Carbonyl sulfide
1594:
1585:
1576:
1534:Silicon monoxide
1467:Hydroxyl radical
1379:
1378:
1359:
1352:
1345:
1336:
1335:
1329:
1328:
1292:
1290:
1289:
1279:
1277:
1276:
1264:
1255:
1254:
1252:
1243:(2): L207–L210.
1230:
1228:
1227:
1213:
1204:
1203:
1201:
1199:
1184:
1178:
1177:
1152:
1146:
1145:
1117:
1111:
1110:
1101:(9): 4073–4074.
1088:
1082:
1081:
1034:
1028:
1027:
995:Nature Chemistry
985:
979:
978:
949:
943:
942:
940:
939:
928:
922:
921:
906:(2nd ed.).
896:
890:
889:
866:
827:
825:
824:
816:
815:
762:
725:
582:The uncatalyzed
562:
547:
539:
528:
483:
428:
422:
419:
418:
361:Chemical formula
284:
283:
268:
266:
250:
230:
219:
208:
197:
186:
166:
146:
122:
45:
41:
37:
21:
4960:
4959:
4955:
4954:
4953:
4951:
4950:
4949:
4940:Vinyl compounds
4925:
4924:
4923:
4918:
4900:
4850:Glycol cleavage
4823:
4819:Ziegler process
4770:
4752:2-Fluoroethanol
4728:
4692:
4676:
4672:Ethylene glycol
4657:1,5-Pentanediol
4636:
4624:
4618:
4591:
4585:
4538:
4521:
4485:Glycylglycitols
4480:
4468:
4462:
4450:
4444:
4440:
4430:
4420:
4410:
4400:
4390:
4380:
4370:
4360:
4350:
4340:
4330:
4325:Ethylene glycol
4320:
4308:
4304:
4287:
4238:
4236:
4230:
4181:
4175:
4147:
4090:
4086:
4076:
4062:
4052:
4038:
4024:
4019:Ethylene glycol
4014:Pentaerythritol
4000:
3984:
3975:Ethylene glycol
3963:
3959:
3949:
3939:
3929:
3919:
3909:
3890:Hydric alcohols
3885:
3803:
3797:
3699:1-Phenylethanol
3692:
3686:
3667:Salicyl alcohol
3632:Isoamyl alcohol
3588:
3539:1-Tetracontanol
3532:
3528:
3524:
3522:
3516:
3457:
3453:
3449:
3447:
3441:
3380:
3376:
3372:
3370:
3364:
3302:
3298:
3294:
3292:
3286:
3233:
3229:
3225:
3223:
3217:
3186:
3182:Tribromoethanol
3117:2-Fluoroethanol
3112:2-Ethoxyethanol
3107:2-Chloroethanol
3102:2-Butoxyethanol
3058:
3044:Methoxymethanol
3010:
2999:
2976:
2949:Medical alcohol
2943:
2908:Isoamyl alcohol
2884:
2870:
2865:
2835:
2830:
2820:
2818:
2808:
2806:
2796:
2794:
2774:
2600:
2576:
2567:
2520:
2510:
2453:
2441:
2422:Propionaldehyde
2397:Ethylene glycol
2386:
2378:
2374:
2345:
2343:
2336:
2292:Cyanohexatriyne
2278:
2271:
2218:
2211:
2146:
2139:
2099:
2052:
2045:
2016:Methoxy radical
1946:
1939:
1935:Thiocyanic acid
1816:
1809:
1719:
1659:Ethynyl radical
1595:
1589:
1588:
1587:
1586:
1580:
1579:
1578:
1577:
1568:
1559:Sulfur monoxide
1544:Sodium chloride
1529:Silicon carbide
1436:Diatomic carbon
1426:Carbon monoxide
1368:
1363:
1333:
1332:
1288:
1285:
1284:
1283:
1281:
1275:
1272:
1271:
1270:
1268:
1265:
1258:
1226:
1223:
1222:
1221:
1219:
1214:
1207:
1197:
1195:
1185:
1181:
1153:
1149:
1142:
1118:
1114:
1089:
1085:
1035:
1031:
991:
986:
982:
950:
946:
937:
935:
929:
925:
918:
897:
893:
887:
867:
860:
855:
823:
820:
819:
818:
814:
811:
810:
809:
807:
797:molecular cloud
793:
786:
782:
773:metal complexes
769:
756:
750:
746:
738:
732:
728:
724:
718:
714:
707:
682:
675:
664:
657:
645:
643:
634:
632:
623:
616:
560:
556:
552:
545:
541:
537:
533:
510:
502:ethylene glycol
494:
477:
468:
447:
440:
435:
434:
433: ?)
424:
420:
416:
412:
396:
373:
369:
363:
349:
346:
341:
340:
329:
326:
325:
322:
316:
315:
309:
308:
305:
299:
298:
287:
269:
262:
253:
233:
220:
189:
169:
149:
136:
125:
112:
98:
96:
95:Hydroxyethylene
94:
86:
85:
36:
23:
22:
15:
12:
11:
5:
4958:
4948:
4947:
4942:
4937:
4920:
4919:
4917:
4916:
4905:
4902:
4901:
4899:
4898:
4893:
4888:
4883:
4881:carbonyl group
4874:
4869:
4864:
4859:
4854:
4853:
4852:
4842:
4837:
4831:
4829:
4825:
4824:
4822:
4821:
4816:
4807:
4798:
4796:Ether cleavage
4793:
4788:
4778:
4776:
4772:
4771:
4769:
4768:
4763:
4761:-butyl alcohol
4754:
4749:
4744:
4738:
4736:
4734:Fluoroalcohols
4730:
4729:
4727:
4726:
4721:
4716:
4711:
4706:
4700:
4698:
4694:
4693:
4691:
4690:
4684:
4682:
4678:
4677:
4675:
4674:
4669:
4664:
4659:
4654:
4652:1,4-Butanediol
4648:
4646:
4642:
4641:
4638:
4637:
4635:
4634:
4628:
4626:
4620:
4619:
4617:
4616:
4611:
4606:
4601:
4595:
4593:
4587:
4586:
4584:
4583:
4578:
4573:
4568:
4563:
4558:
4553:
4548:
4542:
4540:
4531:
4527:
4526:
4523:
4522:
4520:
4519:
4514:
4512:Maltotetraitol
4509:
4504:
4499:
4494:
4488:
4486:
4482:
4481:
4479:
4478:
4472:
4470:
4464:
4463:
4461:
4460:
4454:
4452:
4446:
4445:
4443:
4442:
4438:
4432:
4428:
4422:
4418:
4412:
4408:
4402:
4398:
4392:
4388:
4382:
4378:
4372:
4368:
4362:
4358:
4352:
4348:
4342:
4338:
4332:
4328:
4322:
4318:
4311:
4309:
4306:
4302:
4295:
4293:Sugar alcohols
4289:
4288:
4286:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4253:Erucyl alcohol
4250:
4244:
4242:
4240:fatty alcohols
4232:
4231:
4229:
4228:
4223:
4218:
4213:
4208:
4203:
4201:Lauryl alcohol
4198:
4193:
4187:
4185:
4183:fatty alcohols
4177:
4176:
4174:
4173:
4168:
4163:
4161:Benzyl alcohol
4157:
4155:
4149:
4148:
4146:
4145:
4140:
4135:
4130:
4125:
4120:
4115:
4110:
4104:
4102:
4096:
4095:
4092:
4091:
4089:
4088:
4084:
4078:
4074:
4064:
4060:
4054:
4050:
4040:
4036:
4026:
4022:
4016:
4010:
4008:
4002:
4001:
3999:
3998:
3992:
3990:
3986:
3985:
3983:
3982:
3977:
3971:
3969:
3965:
3964:
3962:
3961:
3957:
3951:
3947:
3941:
3937:
3931:
3927:
3921:
3917:
3911:
3907:
3900:
3898:
3891:
3887:
3886:
3884:
3883:
3878:
3873:
3871:-Butyl alcohol
3865:
3857:
3855:-butyl alcohol
3848:
3846:Methylpentynol
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3807:
3805:
3799:
3798:
3796:
3791:
3786:
3781:
3776:
3771:
3766:
3761:
3756:
3751:
3746:
3741:
3736:
3731:
3726:
3721:
3716:
3711:
3706:
3701:
3696:
3694:
3688:
3687:
3685:
3684:
3679:
3674:
3669:
3664:
3659:
3654:
3649:
3644:
3639:
3634:
3629:
3624:
3622:Crotyl alcohol
3619:
3614:
3612:Benzyl alcohol
3609:
3607:Anisyl alcohol
3604:
3599:
3597:2-Ethylhexanol
3593:
3590:
3589:
3587:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3535:
3533:
3530:
3526:
3521:Straight-chain
3518:
3517:
3515:
3514:
3509:
3504:
3499:
3494:
3489:
3483:
3478:
3472:
3467:
3464:1-Triacontanol
3460:
3458:
3455:
3451:
3446:Straight-chain
3443:
3442:
3440:
3439:
3434:
3428:
3426:1-Heptacosanol
3423:
3417:
3415:1-Pentacosanol
3412:
3409:1-Tetracosanol
3406:
3401:
3395:
3393:1-Heneicosanol
3390:
3383:
3381:
3378:
3374:
3369:Straight-chain
3366:
3365:
3363:
3362:
3357:
3351:
3349:1-Heptadecanol
3346:
3340:
3338:1-Pentadecanol
3335:
3332:1-Tetradecanol
3329:
3324:
3318:
3312:
3305:
3303:
3300:
3296:
3291:Straight-chain
3288:
3287:
3285:
3284:
3278:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3236:
3234:
3231:
3227:
3222:Straight-chain
3219:
3218:
3216:
3215:
3207:
3202:
3196:
3194:
3188:
3187:
3185:
3184:
3179:
3177:Phenoxyethanol
3174:
3166:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3072:1-Aminoethanol
3068:
3066:
3060:
3059:
3057:
3056:
3051:
3046:
3041:
3036:
3031:
3025:
3023:
3014:
3005:
3004:
3001:
3000:
2998:
2997:
2992:
2986:
2984:
2982:Toxic alcohols
2978:
2977:
2975:
2974:
2973:
2972:
2964:
2962:Methylpentynol
2959:
2953:
2951:
2945:
2944:
2942:
2941:
2936:
2934:-Butyl alcohol
2928:
2920:
2915:
2910:
2905:
2900:
2895:
2889:
2887:
2876:
2875:By consumption
2872:
2871:
2864:
2863:
2856:
2849:
2841:
2832:
2831:
2829:
2828:
2816:
2804:
2792:
2779:
2776:
2775:
2773:
2772:
2767:
2762:
2757:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2666:
2661:
2659:Cosmochemistry
2656:
2651:
2646:
2641:
2636:
2631:
2626:
2624:Astrochemistry
2621:
2616:
2610:
2608:
2602:
2601:
2599:
2598:
2593:
2588:
2583:
2578:
2574:
2570:
2565:
2561:
2556:
2551:
2546:
2541:
2536:
2530:
2528:
2522:
2521:
2519:
2518:
2513:
2508:
2504:
2499:
2494:
2489:
2484:
2479:
2477:Formyl radical
2474:
2469:
2463:
2457:
2455:
2447:
2446:
2443:
2442:
2440:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2407:Methyl acetate
2404:
2399:
2394:
2389:
2384:
2380:
2376:
2372:
2366:
2361:
2356:
2350:
2348:
2338:
2337:
2335:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2297:Dimethyl ether
2294:
2289:
2283:
2281:
2273:
2272:
2270:
2269:
2264:
2262:Methyl formate
2259:
2254:
2249:
2247:Glycolaldehyde
2244:
2239:
2234:
2229:
2223:
2221:
2213:
2212:
2210:
2209:
2204:
2199:
2194:
2189:
2184:
2182:Glycolonitrile
2179:
2177:Ethylene oxide
2174:
2169:
2168:
2167:
2157:
2151:
2149:
2141:
2140:
2138:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2097:
2093:
2088:
2083:
2078:
2076:Cyclopropenone
2073:
2068:
2063:
2057:
2055:
2047:
2046:
2044:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1978:
1976:Cyanoacetylene
1973:
1968:
1963:
1958:
1951:
1949:
1941:
1940:
1938:
1937:
1932:
1927:
1922:
1917:
1912:
1907:
1902:
1897:
1895:Methyl radical
1892:
1887:
1882:
1877:
1872:
1870:Isocyanic acid
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1835:Isocyanic acid
1832:
1827:
1821:
1819:
1811:
1810:
1808:
1807:
1802:
1797:
1792:
1787:
1782:
1780:Sulfur dioxide
1777:
1772:
1767:
1762:
1757:
1755:Sodium cyanide
1752:
1747:
1742:
1737:
1732:
1727:
1722:
1717:
1713:
1708:
1703:
1698:
1693:
1688:
1683:
1678:
1672:
1666:
1664:Formyl radical
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1624:Carbon dioxide
1621:
1616:
1611:
1605:
1603:
1597:
1596:
1571:
1569:
1567:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
1531:
1526:
1521:
1516:
1511:
1505:
1500:
1495:
1489:
1484:
1479:
1474:
1472:Iron(II) oxide
1469:
1464:
1458:
1453:
1448:
1443:
1438:
1433:
1428:
1423:
1418:
1413:
1408:
1403:
1398:
1393:
1387:
1385:
1376:
1370:
1369:
1362:
1361:
1354:
1347:
1339:
1331:
1330:
1286:
1273:
1256:
1250:10.1086/324762
1224:
1205:
1179:
1147:
1141:978-3527306732
1140:
1112:
1083:
1029:
1002:(6): 443−448.
989:
980:
944:
923:
916:
891:
885:
857:
856:
854:
851:
838:unimolecularly
830:ethylene oxide
821:
812:
792:
789:
784:
780:
768:
765:
764:
763:
752:
748:
744:
734:
730:
726:
720:
716:
715:=CHOAc → (CH
712:
681:
678:
673:
662:
655:
641:
639:
630:
628:
621:
614:
576:Wacker process
564:
563:
558:
554:
543:
535:
530:
529:
509:
506:
500:of water from
493:
490:
475:
452:, also called
445:
442:
441:
436:
414:
413:
409:standard state
406:
403:
402:
397:
394:
391:
390:
386:
385:
382:
376:
375:
371:
367:
364:
359:
356:
355:
351:
350:
348:
347:
344:
336:
335:
334:
331:
330:
328:
327:
323:
320:
319:
317:
313:
312:
310:
306:
303:
302:
294:
293:
292:
289:
288:
286:
285:
272:
270:
258:
255:
254:
252:
251:
243:
241:
235:
234:
232:
231:
223:
221:
213:
210:
209:
199:
191:
190:
188:
187:
179:
177:
171:
170:
168:
167:
159:
157:
151:
150:
148:
147:
139:
137:
130:
127:
126:
124:
123:
115:
113:
108:
105:
104:
100:
99:
92:
88:
87:
83:
82:
76:
75:
71:
70:
67:
66:
56:
39:Vinyl alcohol
9:
6:
4:
3:
2:
4957:
4946:
4943:
4941:
4938:
4936:
4933:
4932:
4930:
4915:
4907:
4906:
4903:
4897:
4894:
4892:
4889:
4887:
4884:
4882:
4878:
4875:
4873:
4870:
4868:
4865:
4863:
4860:
4858:
4855:
4851:
4848:
4847:
4846:
4843:
4841:
4838:
4836:
4835:Deprotonation
4833:
4832:
4830:
4826:
4820:
4817:
4815:
4811:
4808:
4806:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4783:
4780:
4779:
4777:
4773:
4767:
4764:
4762:
4760:
4755:
4753:
4750:
4748:
4745:
4743:
4740:
4739:
4737:
4735:
4731:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4701:
4699:
4695:
4689:
4686:
4685:
4683:
4679:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4649:
4647:
4643:
4633:
4630:
4629:
4627:
4621:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4596:
4594:
4590:Sesquiterpene
4588:
4582:
4579:
4577:
4574:
4572:
4569:
4567:
4564:
4562:
4559:
4557:
4554:
4552:
4549:
4547:
4544:
4543:
4541:
4535:
4532:
4528:
4518:
4515:
4513:
4510:
4508:
4505:
4503:
4500:
4498:
4495:
4493:
4490:
4489:
4487:
4483:
4477:
4474:
4473:
4471:
4465:
4459:
4456:
4455:
4453:
4447:
4436:
4433:
4426:
4423:
4416:
4413:
4406:
4403:
4396:
4393:
4386:
4383:
4376:
4373:
4366:
4363:
4356:
4353:
4346:
4343:
4336:
4333:
4326:
4323:
4316:
4313:
4312:
4310:
4299:
4296:
4294:
4290:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4268:Oleyl alcohol
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4245:
4243:
4241:
4233:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4188:
4186:
4184:
4178:
4172:
4169:
4167:
4164:
4162:
4159:
4158:
4156:
4154:
4150:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4105:
4103:
4101:
4100:Amyl alcohols
4097:
4082:
4079:
4072:
4068:
4065:
4058:
4055:
4048:
4044:
4041:
4034:
4030:
4027:
4020:
4017:
4015:
4012:
4011:
4009:
4007:
4003:
3997:
3994:
3993:
3991:
3987:
3981:
3978:
3976:
3973:
3972:
3970:
3966:
3955:
3954:Cetyl alcohol
3952:
3945:
3942:
3935:
3932:
3925:
3922:
3915:
3912:
3905:
3902:
3901:
3899:
3895:
3892:
3888:
3882:
3879:
3877:
3874:
3872:
3870:
3866:
3864:
3863:-Amyl alcohol
3862:
3858:
3856:
3854:
3849:
3847:
3844:
3842:
3841:Ethchlorvynol
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3808:
3806:
3804:alcohols (3°)
3800:
3795:
3792:
3790:
3787:
3785:
3782:
3780:
3777:
3775:
3772:
3770:
3769:Cyclopropanol
3767:
3765:
3764:Cyclopentanol
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3705:
3702:
3700:
3697:
3695:
3693:alcohols (2°)
3689:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3653:
3650:
3648:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3602:Allyl alcohol
3600:
3598:
3595:
3594:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3536:
3534:
3519:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3487:
3484:
3482:
3479:
3476:
3473:
3471:
3468:
3465:
3462:
3461:
3459:
3444:
3438:
3437:1-Nonacosanol
3435:
3432:
3431:1-Octacosanol
3429:
3427:
3424:
3421:
3420:1-Hexacosanol
3418:
3416:
3413:
3410:
3407:
3405:
3402:
3399:
3396:
3394:
3391:
3388:
3385:
3384:
3382:
3367:
3361:
3360:1-Nonadecanol
3358:
3355:
3354:1-Octadecanol
3352:
3350:
3347:
3344:
3343:1-Hexadecanol
3341:
3339:
3336:
3333:
3330:
3328:
3325:
3322:
3319:
3316:
3313:
3310:
3307:
3306:
3304:
3289:
3282:
3279:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3237:
3235:
3220:
3214:
3212:
3208:
3206:
3203:
3201:
3198:
3197:
3195:
3193:
3189:
3183:
3180:
3178:
3175:
3173:
3171:
3167:
3165:
3163:
3159:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3069:
3067:
3065:
3061:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3034:Aminomethanol
3032:
3030:
3027:
3026:
3024:
3022:
3018:
3015:
3012:
3006:
2996:
2993:
2991:
2988:
2987:
2985:
2983:
2979:
2971:
2968:
2967:
2965:
2963:
2960:
2958:
2957:Ethchlorvynol
2955:
2954:
2952:
2950:
2946:
2940:
2937:
2935:
2933:
2929:
2927:
2926:-Amyl alcohol
2925:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2890:
2888:
2886:
2880:
2877:
2873:
2869:
2862:
2857:
2855:
2850:
2848:
2843:
2842:
2839:
2827:
2817:
2815:
2805:
2803:
2793:
2791:
2790:
2781:
2780:
2777:
2771:
2768:
2766:
2763:
2761:
2758:
2755:
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2689:Homochirality
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2611:
2609:
2607:
2603:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2577:
2571:
2569:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2544:Methoxyethane
2542:
2540:
2537:
2535:
2532:
2531:
2529:
2527:
2523:
2517:
2514:
2512:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2467:
2464:
2462:
2459:
2458:
2456:
2452:
2448:
2438:
2435:
2433:
2430:
2428:
2427:Butyronitrile
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2402:Ethyl formate
2400:
2398:
2395:
2393:
2390:
2388:
2381:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2351:
2349:
2347:
2339:
2333:
2330:
2328:
2327:Propionitrile
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2284:
2282:
2280:
2274:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2224:
2222:
2220:
2214:
2208:
2207:Vinyl alcohol
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2166:
2165:Vinyl cyanide
2163:
2162:
2161:
2160:Acrylonitrile
2158:
2156:
2153:
2152:
2150:
2148:
2142:
2136:
2133:
2131:
2128:
2126:
2125:Pentynylidyne
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2058:
2056:
2054:
2048:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2021:Methylenimine
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1956:
1953:
1952:
1950:
1948:
1942:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1900:Propynylidyne
1898:
1896:
1893:
1891:
1890:Methyl cation
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1850:Fulminic acid
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1822:
1820:
1818:
1812:
1806:
1803:
1801:
1798:
1796:
1793:
1791:
1788:
1786:
1783:
1781:
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1736:
1733:
1731:
1728:
1726:
1725:Nitrous oxide
1723:
1721:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1676:
1673:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1619:Amino radical
1617:
1615:
1612:
1610:
1607:
1606:
1604:
1602:
1598:
1593:
1584:
1575:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1549:Sodium iodide
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1530:
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1509:
1506:
1504:
1501:
1499:
1496:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1462:
1459:
1457:
1454:
1452:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1431:Cyano radical
1429:
1427:
1424:
1422:
1419:
1417:
1414:
1412:
1411:Carbon cation
1409:
1407:
1404:
1402:
1399:
1397:
1394:
1392:
1389:
1388:
1386:
1384:
1380:
1377:
1375:
1371:
1367:
1360:
1355:
1353:
1348:
1346:
1341:
1340:
1337:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1297:
1263:
1261:
1251:
1246:
1242:
1238:
1237:
1232:
1212:
1210:
1194:
1190:
1183:
1175:
1171:
1168:(8): 2483–6.
1167:
1163:
1162:
1157:
1156:Cotton, F. A.
1151:
1143:
1137:
1133:
1129:
1125:
1124:
1116:
1108:
1104:
1100:
1096:
1095:
1087:
1079:
1075:
1071:
1067:
1063:
1059:
1055:
1051:
1047:
1043:
1042:
1033:
1025:
1021:
1017:
1013:
1009:
1005:
1001:
997:
996:
984:
976:
972:
968:
964:
960:
957:
956:
948:
934:
927:
919:
913:
909:
905:
901:
895:
888:
882:
878:
877:
872:
865:
863:
858:
850:
848:
843:
839:
835:
831:
805:
801:
800:Sagittarius B
798:
788:
778:
774:
760:
755:
742:
737:
727:
723:
710:
706:
705:
704:
702:
698:
694:
693:vinyl acetate
690:
687:
686:thermoplastic
677:
672:
668:
661:
653:
649:
638:
627:
620:
613:
609:
605:
600:
596:
594:
593:Carbonic acid
589:
585:
577:
573:
568:
551:
550:
549:
527:
523:
522:
521:
519:
515:
505:
503:
499:
489:
487:
481:
474:
471:
467:
463:
459:
455:
451:
450:Vinyl alcohol
439:
432:
427:
410:
404:
401:
400:Allyl alcohol
398:
393:
392:
387:
383:
381:
378:
377:
365:
362:
358:
357:
352:
343:
342:
339:
332:
318:
311:
301:
300:
297:
290:
282:
278:
277:DTXSID8051467
274:
273:
271:
261:
257:
256:
249:
245:
244:
242:
240:
237:
236:
229:
225:
224:
222:
216:
212:
211:
207:
203:
200:
198:
196:ECHA InfoCard
193:
192:
185:
181:
180:
178:
176:
173:
172:
165:
161:
160:
158:
156:
153:
152:
145:
141:
140:
138:
134:
129:
128:
121:
117:
116:
114:
111:
107:
106:
101:
93:Hydroxyethene
89:
81:
77:
72:
61:
57:
51:
47:
46:
42:
34:
30:
19:
4782:Substitution
4775:Preparations
4758:
4724:Stigmasterol
4719:β-Sitosterol
4517:Polyglycitol
4507:Maltotriitol
4467:Cyclic sugar
4235:Branched and
4143:Pentan-3-ol
4138:Pentan-2-ol
4133:Pentan-1-ol
3868:
3860:
3852:
3759:Cyclohexanol
3411:(lignoceryl)
3404:1-Tricosanol
3327:1-Tridecanol
3283:(pelargonic)
3210:
3169:
3161:
3157:
3152:Ethanolamine
2931:
2923:
2782:
2765:Spectroscopy
2619:Astrobiology
2472:Formaldehyde
2364:Benzonitrile
2206:
2155:Acetaldehyde
2110:Methanethiol
2061:Acetonitrile
1966:Carbodiimide
1845:Formaldehyde
1840:Cyanoethynyl
1691:Iron cyanide
1686:Hydroperoxyl
1487:Nitric oxide
1300:
1296:ChemPhysChem
1294:
1240:
1234:
1198:December 20,
1196:. Retrieved
1182:
1165:
1159:
1150:
1121:
1115:
1098:
1092:
1086:
1045:
1039:
1032:
999:
993:
983:
958:
953:
947:
936:. Retrieved
926:
903:
894:
875:
871:March, Jerry
794:
770:
758:
753:
740:
735:
721:
708:
695:followed by
683:
670:
659:
636:
625:
618:
611:
601:
597:
581:
572:acetaldehyde
557:C=CHOH → H
531:
518:acetaldehyde
514:tautomerizes
511:
495:
486:acetaldehyde
457:
453:
449:
448:
103:Identifiers
91:Other names
4840:Protonation
4757:Nonafluoro-
4704:Cholesterol
4681:Trialcohols
4551:Citronellol
4537:Monoterpene
4449:Deoxy sugar
4237:unsaturated
3924:Isopropanol
3851:Nonafluoro-
3779:Isopropanol
3398:1-Docosanol
3389:(arachidyl)
3321:1-Dodecanol
3315:1-Undecanol
2739:Outer space
2649:Cosmic dust
2614:Abiogenesis
2526:Unconfirmed
2482:Heavy water
2322:Ethanethiol
2237:Cyanoallene
2227:Acetic acid
2197:Methylamine
2081:Diacetylene
1996:Formic acid
1986:Cyanomethyl
1644:Diazenylium
1634:CCP radical
1510:(molecular)
1494:(molecular)
1463:(molecular)
767:As a ligand
652:heavy water
498:elimination
464:. With the
354:Properties
202:100.008.350
164:ChEMBL76101
4929:Categories
4801:Hydrolysis
4786:haloalkane
4714:Lanosterol
4709:Ergosterol
4645:Dialcohols
4614:Patchoulol
4415:Galactitol
4345:Erythritol
4221:Tridecanol
4043:Erythritol
3944:1-Pentanol
3754:3-Pentanol
3749:2-Pentanol
3719:3-Heptanol
3714:2-Heptanol
3672:Tryptophol
3477:(lacceryl)
3387:1-Icosanol
3334:(myristyl)
3317:(hendecyl)
3270:1-Heptanol
3260:1-Pentanol
3250:1-Propanol
3205:Isobutanol
2939:Tryptophol
2913:Isobutanol
2893:1-Propanol
2654:Cosmic ray
2596:Silylidyne
2559:Hemolithin
2534:Anthracene
2451:Deuterated
2432:Pyrimidine
2242:Ethanimine
2105:Ketenimine
1961:Butadiynyl
1785:Thioformyl
1639:Chloronium
938:2014-08-30
853:References
697:hydrolysis
606:-produced
380:Molar mass
248:GO1N1ZPR3B
175:ChemSpider
131:3D model (
110:CAS Number
4828:Reactions
4810:Hydration
4623:Diterpene
4609:Nerolidol
4599:Bisabolol
4581:Terpineol
4435:Volemitol
4226:Undecanol
4180:Saturated
4081:Volemitol
3934:1-Butanol
3744:2-Octanol
3739:2-Nonanol
3729:3-Hexanol
3724:2-Hexanol
3704:2-Butanol
3691:Secondary
3523:saturated
3448:saturated
3400:(behenyl)
3371:saturated
3356:(stearyl)
3309:1-Decanol
3293:saturated
3281:1-Nonanol
3275:1-Octanol
3265:1-Hexanol
3255:1-Butanol
3224:saturated
2586:Phosphine
2454:molecules
2387:fullerene
2287:Acetamide
2091:Formamide
1971:Cyanamide
1825:Acetylene
1800:Tricarbon
1711:Methylene
1696:Isoformyl
1601:Triatomic
1374:Molecules
1325:233447839
747:O → (CH
667:half-life
604:deuterium
492:Synthesis
458:ethylenol
97:Ethylenol
4914:Category
4688:Glycerol
4625:alcohols
4604:Farnesol
4592:alcohols
4576:Rhodinol
4561:Linalool
4556:Geraniol
4539:alcohols
4497:Lactitol
4492:Maltitol
4476:Inositol
4469:alcohols
4451:alcohols
4405:Sorbitol
4395:Mannitol
4365:Arabitol
4355:Threitol
4335:Glycerol
4071:Sorbitol
4067:Mannitol
4047:Threitol
4029:Glycerol
3996:Glycerol
3904:Methanol
3802:Tertiary
3488:(geddyl)
3323:(lauryl)
3311:(capric)
3277:(capryl)
3240:Methanol
3213:-Butanol
3021:Methanol
3011:alcohols
2995:Methanol
2868:Alcohols
2573:Linear C
2554:Graphene
2466:Ammonium
2267:Acrolein
2130:Propynal
2115:Methanol
2086:Ethylene
1955:Ammonium
1730:Nitroxyl
1554:Sulfanyl
1498:Imidogen
1492:Nitrogen
1461:Hydrogen
1406:Argonium
1383:Diatomic
1317:33913232
1078:42079807
1070:22903524
1024:21602858
975:19834921
873:(2007),
771:Several
624:= 4.75,
374:O
120:557-75-5
4805:epoxide
4697:Sterols
4566:Menthol
4546:Borneol
4502:Isomalt
4458:Fucitol
4385:Xylitol
4375:Ribitol
4216:Octanol
4211:Nonanol
4196:Decanol
4057:Xylitol
3914:Ethanol
3422:(ceryl)
3245:Ethanol
3192:Butanol
3147:Ethanol
3064:Ethanol
3009:Primary
2970:Ethanol
2903:Ethanol
2719:Kerogen
2606:Related
2549:Glycine
2502:Propyne
2461:Ammonia
2359:Benzene
2354:Acetone
2346:or more
2317:Propene
2302:Ethanol
2192:Propyne
2011:Methane
1880:Ketenyl
1830:Ammonia
1291:CCH(OH)
1050:Bibcode
1041:Science
1004:Bibcode
804:isomers
787:OH)Cl.
733:−CHOAc)
719:−CHOAc)
699:of the
466:formula
454:ethenol
431:what is
429: (
215:PubChem
84:Ethenol
33:ethynol
29:ethanol
18:Ethenol
4814:alkene
4632:Phytol
4425:Iditol
3657:Prenol
2770:Tholin
2591:Pyrene
2036:Silane
2006:Ketene
1508:Oxygen
1323:
1315:
1138:
1076:
1068:
1022:
973:
914:
883:
777:ligand
751:−CHOH)
648:ketene
561:CC(O)H
546:C=CHOH
538:CC(O)H
426:verify
423:
338:SMILES
155:ChEMBL
74:Names
4935:Enols
4571:Nerol
2756:(PAH)
2344:atoms
2279:atoms
2219:atoms
2217:Eight
2147:atoms
2145:Seven
2053:atoms
1947:atoms
1817:atoms
1805:Water
1735:Ozone
1677:(HNC)
1671:(HCN)
1321:S2CID
1229:=CHOH
1074:S2CID
701:ester
516:) to
296:InChI
228:11199
184:10726
133:JSmol
4759:tert
3869:tert
3861:tert
3853:tert
3013:(1°)
2932:tert
2924:tert
2277:Nine
1945:Five
1855:HCCN
1815:Four
1775:SiNC
1313:PMID
1200:2006
1136:ISBN
1066:PMID
1020:PMID
971:PMID
912:ISBN
881:ISBN
761:HOAc
462:enol
345:OC=C
239:UNII
4879:of
4812:of
4803:of
4784:of
4305:— C
3529:— C
3454:— C
3377:— C
3299:— C
3230:— C
2568:NCO
2468:ion
2375:, C
2342:Ten
2051:Six
1957:ion
1305:doi
1278:CHO
1245:doi
1241:561
1170:doi
1128:doi
1103:doi
1099:100
1058:doi
1046:337
1012:doi
963:doi
806:of
729:(CH
674:1/2
265:EPA
218:CID
31:or
4931::
4437:(C
4427:(C
4417:(C
4407:(C
4397:(C
4387:(C
4377:(C
4367:(C
4357:(C
4347:(C
4337:(C
4327:(C
4317:(C
4083:(C
4073:(C
4069:,
4059:(C
4049:(C
4045:,
4035:(C
4031:,
4021:(C
3958:16
3956:(C
3946:(C
3936:(C
3926:(C
3916:(C
3906:(C
3531:49
3527:40
3456:39
3452:30
3379:29
3375:20
3301:19
3297:10
2385:70
2377:60
2373:60
2371:(C
2096:HC
1319:.
1311:.
1301:22
1299:.
1269:CH
1259:^
1239:.
1233:.
1220:CH
1208:^
1166:95
1164:.
1134:.
1097:.
1072:.
1064:.
1056:.
1044:.
1018:.
1010:.
998:.
969:.
959:48
861:^
849:.
757:+
739:+
711:CH
654:(D
520::
478:CH
4441:)
4439:7
4431:)
4429:6
4421:)
4419:6
4411:)
4409:6
4401:)
4399:6
4391:)
4389:5
4381:)
4379:5
4371:)
4369:5
4361:)
4359:4
4351:)
4349:4
4341:)
4339:3
4331:)
4329:2
4321:)
4319:1
4307:7
4303:1
4301:C
4087:)
4085:7
4077:)
4075:6
4063:)
4061:5
4053:)
4051:4
4039:)
4037:3
4025:)
4023:2
3960:)
3950:)
3948:5
3940:)
3938:4
3930:)
3928:3
3920:)
3918:2
3910:)
3908:1
3525:C
3450:C
3373:C
3295:C
3232:9
3228:1
3226:C
3211:n
3170:N
3162:N
3160:,
3158:N
2860:e
2853:t
2846:v
2575:5
2566:2
2564:H
2511:D
2509:2
2507:N
2383:C
2100:N
2098:4
1720:H
1718:2
1716:N
1358:e
1351:t
1344:v
1327:.
1307::
1287:2
1282:H
1274:3
1253:.
1247::
1231:"
1225:2
1202:.
1176:.
1172::
1144:.
1130::
1109:.
1105::
1080:.
1060::
1052::
1026:.
1014::
1006::
1000:3
990:3
977:.
965::
941:.
920:.
826:O
822:4
817:H
813:2
808:C
785:3
783:H
781:2
759:n
754:n
749:2
745:2
743:H
741:n
736:n
731:2
722:n
717:2
713:2
709:n
671:t
663:t
660:k
656:2
644:O
642:2
640:D
637:k
635:/
633:O
631:2
629:H
626:k
622:D
619:k
617:/
615:H
612:k
610:(
574:(
559:3
555:2
553:H
544:2
542:H
536:3
534:H
482:H
480:O
476:2
473:H
470:C
421:Y
372:4
370:H
368:2
366:C
267:)
263:(
135:)
35:.
20:)
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