515:
1581:
270:
195:
556:
49:
2810:
1563:
4899:
2774:
39:
1572:
2798:
2786:
406:
579:
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
587:
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.
833:
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
1026:
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".
1080:
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".
977:
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
2123:
1893:
1853:
1345:
2054:
2029:
2019:
2871:
3562:
3552:
3547:
2425:
1753:
1694:
1602:
4261:
3804:
3572:
3567:
3557:
3490:
3480:
3474:
2514:
2330:
2265:
2205:
2133:
2039:
1933:
1803:
1758:
1429:
2594:
3819:
3809:
3542:
3532:
3500:
3495:
3485:
2059:
1903:
1873:
4246:
3697:
3537:
3469:
3458:
1989:
1969:
1642:
2014:
419:
3527:
1111:
4500:
4241:
3403:
1652:
1354:
2009:
1338:
4933:
4505:
4495:
3392:
1679:
2225:
1622:
1773:
326:
1684:
1331:
2552:
1868:
1149:
1082:
591:
Vinyl alcohol can be stabilized by controlling the water concentration in the system and utilizing the kinetic favorability of the
584:
is another example of a substance that is stable when rigorously pure, but decomposes rapidly due to catalysis by trace moisture.)
2084:
1843:
1763:
904:
873:
2465:
1181:
414:
2847:
2717:
1128:
4850:
4650:
2617:
1147:; Francis, J. N.; Frenz, B. A.; Tsutsui, M. (1973). "Structure of a dihapto(vinyl alcohol) complex of platinum(II)".
284:
426:
4879:
2742:
537:) by 42.7 kJ/mol. Vinyl alcohol gas isomerizes to the aldehyde with a half-life of 30 min at room temperature.
941:
Keith, J. A.; Henry, P. M. (2009). "The
Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations".
4745:
3839:
3782:
2667:
2702:
227:
190:
48:
4793:
3145:
3017:
1898:
863:
576:
248:
152:
4855:
4154:
3085:
3080:
647:
O). Studies show that the tautomerization process is significantly inhibited at ambient temperatures (
4874:
4865:
4845:
3075:
2657:
2652:
1833:
1224:
572:
4928:
4199:
2697:
477:
immediately upon isolation near room temperature. It is not a practical precursor to any compound.
265:
38:
4730:
4096:
2777:
896:
4735:
3120:
3070:
3065:
2840:
2632:
1597:
1507:
1384:
1379:
596:
514:
4770:
4159:
2687:
2662:
2300:
1918:
1465:
943:
4860:
3157:
3130:
2748:
2732:
2357:
1728:
1699:
1580:
1404:
1038:
992:
835:
761:
486:
236:
172:
68:
8:
4884:
4236:
4179:
4141:
3814:
3799:
3777:
3125:
3037:
2937:
2856:
2692:
2672:
2485:
2175:
1663:
1527:
1502:
1470:
1389:
822:
132:
108:
98:
1042:
996:
269:
194:
4798:
4779:
4655:
4271:
4116:
4111:
4106:
4101:
3856:
3722:
3188:
3027:
2919:
2886:
2790:
2712:
2682:
2627:
2504:
2480:
1979:
1913:
1778:
1738:
1589:
1552:
1512:
1491:
1434:
1409:
1309:
1062:
1256:
Kleimeier, N. Fabian; Kaiser, Ralf I. (2021). "Interstellar
Enolization-Acetaldehyde (
4902:
4833:
4754:
4266:
3869:
3848:
3824:
3772:
3767:
3670:
3650:
3640:
3630:
3625:
3110:
3042:
2978:
2911:
2906:
2833:
2737:
2320:
2220:
2190:
2108:
1848:
1733:
1689:
1637:
1444:
1439:
1371:
1313:
1301:
1124:
1054:
1029:
1008:
959:
900:
869:
830:
677:
4774:
1323:
1066:
4303:
4251:
4194:
4021:
3968:
3864:
3762:
3665:
3635:
3615:
3605:
3463:
3115:
2814:
2802:
2722:
2622:
2527:
2475:
1908:
1783:
1748:
1669:
1657:
1617:
1522:
1455:
1293:
1233:
1158:
1144:
1116:
1091:
1046:
1000:
983:
951:
888:
454:
349:
216:
4838:
4807:
4740:
4707:
4660:
4645:
4313:
4007:
4002:
3963:
3687:
3655:
3620:
3170:
3105:
3100:
3095:
3090:
3032:
2997:
2896:
2410:
2385:
1923:
1863:
1647:
1547:
1532:
1517:
1424:
1414:
785:
490:
4923:
4869:
4784:
4640:
4189:
4149:
3834:
3610:
3600:
3595:
3585:
3452:
3414:
3397:
3381:
3337:
3326:
3320:
3165:
3060:
2950:
2647:
2612:
2395:
2285:
2250:
2235:
2170:
2165:
2064:
1964:
1883:
1858:
1823:
1768:
1743:
1612:
1460:
818:
788:
564:
397:
555:
4917:
4823:
4722:
4281:
4256:
4228:
4171:
3994:
3942:
3829:
3757:
3752:
3590:
3425:
3419:
3408:
3348:
3342:
3331:
3022:
2970:
2945:
2677:
2532:
2415:
2390:
2371:
2315:
2153:
2148:
1888:
1878:
1838:
1713:
1607:
1562:
1537:
1419:
1399:
1120:
681:
674:
581:
388:
183:
1050:
4712:
4088:
3747:
3315:
3140:
2753:
2607:
2460:
2400:
2380:
2352:
2280:
2160:
2143:
2098:
2049:
1954:
1674:
1627:
1475:
1305:
1297:
1284:
1058:
1012:
963:
955:
826:
635:= 12). Deuterium stabilization can be accomplished through hydrolysis of a
580:
only be stored for minutes to hours before it isomerizes to acetaldehyde. (
560:
506:
474:
1177:
4828:
4802:
4692:
4539:
4131:
4126:
4121:
3912:
3386:
3309:
3303:
2727:
2637:
2602:
2569:
2495:
2470:
2310:
2215:
2185:
2069:
1984:
1974:
1704:
1632:
859:
640:
1162:
1095:
4789:
4702:
4697:
4602:
4403:
4333:
4209:
4031:
3932:
3742:
3737:
3707:
3702:
3660:
3375:
3258:
3248:
3238:
3193:
2927:
2901:
2881:
2642:
2584:
2547:
2522:
2420:
2230:
2093:
1178:"Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space"
1004:
685:
368:
163:
4597:
4587:
4569:
4423:
4214:
4069:
3922:
3732:
3727:
3717:
3712:
3692:
3297:
3269:
3263:
3253:
3243:
3198:
2574:
2439:
2275:
2079:
1959:
1813:
1788:
655:
592:
396:
Except where otherwise noted, data are given for materials in their
4676:
4592:
4564:
4549:
4544:
4485:
4480:
4464:
4393:
4383:
4353:
4343:
4323:
4059:
4055:
4035:
4017:
3984:
3892:
3228:
3009:
2983:
2542:
2454:
2255:
2118:
2103:
2074:
1943:
1718:
1542:
1486:
1480:
1449:
1394:
1362:
1238:
1206:
502:
496:
461:
131:
4554:
4534:
4490:
4446:
4373:
4363:
4204:
4184:
4045:
3902:
3233:
3180:
3135:
3052:
2958:
2891:
2707:
2537:
2490:
2449:
2405:
2347:
2342:
2305:
2295:
2290:
2245:
2240:
2180:
2113:
2004:
1999:
1949:
1828:
1818:
1571:
203:
21:
17:
1025:
976:
865:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
4620:
4413:
3645:
2758:
2579:
2561:
2024:
1994:
1496:
792:
765:
639:
precursor in the presence of a slight stoichiometric excess of
636:
468:
458:
143:
4559:
1793:
1723:
857:
689:
121:
253:
2825:
921:
868:(6th ed.), New York: Wiley-Interscience, p. 101,
567:) proceeds via the intermediacy of a vinyl alcohol complex.
450:
1143:
821:) to be detected in space. Its stability in the (dilute)
1109:
Hallensleben ML (2000). "Polyvinyl
Compounds, Others".
680:(PVA or PVOH) is made indirectly by polymerization of
668:
1353:
1207:"Microwave Detection of Interstellar Vinyl Alcohol,
887:
779:
1251:
1249:
665:= 42 minutes for first-order hydrolysis kinetics.
493:at a temperature of 900 °C and low pressure.
673:Because of the instability of vinyl alcohol, the
501:Under normal conditions, vinyl alcohol converts (
4915:
1246:
575:by a 1,3-hydrogen migration is forbidden by the
497:Tautomerization of vinyl alcohol to acetaldehyde
215:
1255:
825:shows that its tautomerization does not happen
107:
1112:Ullmann's Encyclopedia of Industrial Chemistry
1079:
2841:
1339:
485:Vinyl alcohol can be formed by the pyrolytic
1204:
1108:
919:
658:of the enol form can easily be increased to
473:, it is a labile compound that converts to
2848:
2834:
1346:
1332:
1200:
1198:
940:
764:are known that contain vinyl alcohol as a
268:
193:
171:
1237:
922:"CCCBDB NIST Standard Reference Database"
692:bonds (Ac = acetyl; HOAc = acetic acid):
235:
1150:Journal of the American Chemical Society
1083:Journal of the American Chemical Society
891:; Greeves, Nick; Warren, Stuart (2012).
554:
1195:
853:
851:
829:, a fact attributed to the size of the
264:
4916:
1102:
934:
791:in 2001, the last of the three stable
184:
4934:Organic compounds with 2 carbon atoms
2829:
1327:
1205:Turner, B. E.; Apponi, A. J. (2001).
529:) is more stable than vinyl alcohol (
313:Key: IMROMDMJAWUWLK-UHFFFAOYSA-N
296:Key: IMROMDMJAWUWLK-UHFFFAOYSA-N
151:
3995:Polyhydric alcohols (sugar alcohols)
1182:National Radio Astronomy Observatory
1175:
848:
669:Relationship to poly(vinyl alcohol)
521:At room temperature, acetaldehyde (
206:
13:
2718:Nexus for Exoplanet System Science
784:Vinyl alcohol was detected in the
47:
37:
14:
4945:
4651:2-Methyl-2-propyl-1,3-propanediol
2618:Atomic and molecular astrophysics
1355:Molecules detected in outer space
1176:Blue, Charles (October 1, 2001).
780:Occurrence in interstellar medium
4898:
4897:
2808:
2796:
2784:
2773:
2772:
1579:
1570:
1561:
513:
404:
4880:Nucleophilic conjugate addition
2743:Polycyclic aromatic hydrocarbon
1169:
400:(at 25 °C , 100 kPa).
310:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
303:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
293:InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
52:Ball-and-stick model of ethenol
1137:
1073:
1019:
970:
913:
881:
755:
1:
4851:Fischer–Speier esterification
3783:Propylene glycol methyl ether
2668:Extraterrestrial liquid water
841:
768:. One example is Pt(acac)(η-C
445:(IUPAC name; not ethanol) or
42:Structural formula of ethenol
2855:
559:The industrial synthesis of
480:
7:
3018:4-Methylcyclohexanemethanol
1899:Protonated hydrogen cyanide
33:
10:
4950:
4856:Williamson ether synthesis
4155:2,4-Dichlorobenzyl alcohol
3086:2-(2-Methoxyethoxy)ethanol
3081:2-(2-Methoxyethoxy)ethanol
373:44.053 g/mol
15:
4893:
4875:Friedel-Crafts alkylation
4866:Nucleophilic substitution
4846:Nucleophilic substitution
4816:
4763:
4721:
4685:
4669:
4633:
4611:
4578:
4525:
4518:
4473:
4455:
4437:
4289:
4280:
4223:
4168:
4140:
4087:
3993:
3977:
3956:
3885:
3878:
3790:
3679:
3509:
3434:
3357:
3279:
3210:
3179:
3076:2-(2-Ethoxyethoxy)ethanol
3051:
3008:
2996:
2969:
2936:
2870:
2863:
2767:
2658:Earliest known life forms
2653:Diffuse interstellar band
2593:
2513:
2438:
2329:
2264:
2204:
2132:
2124:Protonated cyanoacetylene
2038:
1932:
1894:Protonated carbon dioxide
1854:Hydromagnesium isocyanide
1802:
1588:
1559:
1370:
1361:
1225:The Astrophysical Journal
394:
377:
342:
322:
280:
91:
79:
67:
62:
32:
4097:2,2-Dimethylpropan-1-ol
3153:-Diisopropylaminoethanol
2703:Iron–sulfur world theory
2698:Photodissociation region
2401:Methyl-cyano-diacetylene
1121:10.1002/14356007.a21_743
981:CHO photodissociation".
817:(after acetaldehyde and
16:Not to be confused with
4731:1,3-Difluoro-2-propanol
2778:Category:Astrochemistry
2368:, fullerene, buckyball)
2055:Cyanobutadiynyl radical
2030:Silicon-carbide cluster
2020:Protonated formaldehyde
1115:. Weinheim: Wiley-VCH.
1051:10.1126/science.1220712
897:Oxford University Press
577:Woodward–Hoffmann rules
4736:2,2,2-Trifluoroethanol
3121:Aminoethylethanolamine
3071:2,2,2-Trifluoroethanol
3066:2,2,2-Trichloroethanol
2791:Outer space portal
2633:Circumstellar envelope
1598:Aluminium(I) hydroxide
1508:Phosphorus mononitride
1385:Aluminium monofluoride
1380:Aluminium monochloride
1298:10.1002/cphc.202100111
956:10.1002/anie.200902194
597:kinetic isotope effect
568:
53:
43:
4160:3-Nitrobenzyl alcohol
2688:Interplanetary medium
2663:Extraterrestrial life
2301:Octatetraynyl radical
1919:Tricarbon monosulfide
1466:Magnesium monohydride
1269:) and Vinyl Alcohol (
944:Angew. Chem. Int. Ed.
573:keto–enol tautomerism
558:
51:
41:
4861:Elimination reaction
3563:1-Heptatetracontanol
3553:1-Pentatetracontanol
3548:1-Tetratetracontanol
3455:(melissyl / myricyl)
3422:(cluytyl / montanyl)
3131:Dimethylethanolamine
2815:Chemistry portal
2803:Astronomy portal
2749:RNA world hypothesis
2733:PAH world hypothesis
2426:Heptatrienyl radical
2358:Buckminsterfullerene
2246:Methylcyanoacetylene
1754:Silicon carbonitride
1729:Methylidynephosphane
1695:Magnesium isocyanide
1603:Aluminium isocyanide
1405:Carbon monophosphide
1282:) as a Case Study".
836:galactic cosmic rays
69:Preferred IUPAC name
4885:Transesterification
4262:Palmitoleyl alcohol
4237:3-Methyl-3-pentanol
4180:Cetostearyl alcohol
4117:3-Methylbutan-2-ol
4112:3-Methylbutan-1-ol
4107:2-Methylbutan-2-ol
4102:2-Methylbutan-1-ol
3886:Monohydric alcohols
3815:3-Methyl-3-pentanol
3805:2-Methylheptan-2-ol
3800:2-Methyl-2-pentanol
3573:1-Nonatetracontanol
3568:1-Octatetracontanol
3558:1-Hexatetracontanol
3491:1-Heptatriacontanol
3481:1-Pentatriacontanol
3475:1-Tetratriacontanol
3161:-Methylethanolamine
3126:Diethylethanolamine
3038:Methylazoxymethanol
2955:Methanol poisoning
2693:Interstellar medium
2673:Forbidden mechanism
2486:Hydrogen isocyanide
2176:Hexatriynyl radical
1759:c-Silicon dicarbide
1664:Hydrogen isocyanide
1528:Silicon monosulfide
1503:Phosphorus monoxide
1471:Methylidyne radical
1430:Fluoromethylidynium
1390:Aluminium(II) oxide
1163:10.1021/ja00789a011
1096:10.1021/ja00088a051
1043:2012Sci...337.1203A
1037:(6099): 1203–1206.
997:2011NatCh...3..443H
899:. pp. 456–57.
858:Smith, Michael B.;
823:interstellar medium
654:≈ 10 M/s), and the
29:
4780:Carbonyl reduction
4656:Diethylpropanediol
4272:tert-Butyl alcohol
3978:Trihydric alcohols
3820:3-Methyloctan-3-ol
3810:2-Methylhexan-2-ol
3723:3-Methyl-2-butanol
3543:1-Tritetracontanol
3533:1-Hentetracontanol
3501:1-Nonatriacontanol
3496:1-Octatriacontanol
3486:1-Hexatriacontanol
3334:(cetyl / palmityl)
3189:2-Methyl-1-butanol
3028:Cyclohexylmethanol
2887:2-Methyl-1-butanol
2713:Molecules in stars
2683:Intergalactic dust
2628:Circumstellar dust
2570:Naphthalene cation
2505:Trihydrogen cation
2481:Hydrogen deuteride
2406:Methyltriacetylene
2241:Hexapentaenylidene
2060:E-Cyanomethanimine
1980:Cyclopropenylidene
1914:Tricarbon monoxide
1904:Silicon tricarbide
1874:Methylene amidogen
1864:Isothiocyanic acid
1779:Thioxoethenylidene
1739:Trihydrogen cation
1553:Titanium(II) oxide
1513:Potassium chloride
1492:Sulfur mononitride
1435:Helium hydride ion
1410:Carbon monosulfide
1005:10.1038/nchem.1052
920:R.D. Johnson III.
569:
449:, is the simplest
427:Infobox references
378:Related compounds
54:
44:
27:
4911:
4910:
4834:Alcohol oxidation
4755:Trifluoromethanol
4629:
4628:
4514:
4513:
4267:tert-Amyl alcohol
4247:Linolenyl alcohol
4142:Aromatic alcohols
4083:
4082:
3957:Dihydric alcohols
3870:Triphenylmethanol
3825:Diacetone alcohol
3773:Pinacolyl alcohol
3698:2-Deoxyerythritol
3671:Veratrole alcohol
3651:Propargyl alcohol
3641:Phenethyl alcohol
3631:Nicotinyl alcohol
3626:Neopentyl alcohol
3581:
3580:
3538:1-Dotetracontanol
3470:1-Tritriacontanol
3459:1-Hentriacontanol
3111:2-Mercaptoethanol
3043:Trifluoromethanol
2992:
2991:
2979:Isopropyl alcohol
2907:Phenethyl alcohol
2872:Alcohols found in
2823:
2822:
2738:Pseudo-panspermia
2434:
2433:
2381:Cyanodecapentayne
2321:N-Methylformamide
2296:Methyldiacetylene
2221:Aminoacetonitrile
2191:Methyl isocyanate
2109:Methyl isocyanide
1990:Isocyanoacetylene
1970:Cyanoformaldehyde
1849:Hydrogen peroxide
1734:Potassium cyanide
1690:Magnesium cyanide
1643:Disilicon carbide
1638:Dicarbon monoxide
1445:Hydrogen fluoride
1440:Hydrogen chloride
1292:(12): 1229–1236.
1180:(Press release).
950:(48): 9038–9049.
906:978-0-19-927029-3
893:Organic Chemistry
889:Clayden, Jonathan
875:978-0-471-72091-1
831:activation energy
678:polyvinyl alcohol
435:Chemical compound
433:
432:
384:Related compounds
249:CompTox Dashboard
133:Interactive image
58:
57:
4941:
4901:
4900:
4523:
4522:
4519:Terpene alcohols
4304:Methylene glycol
4287:
4286:
4252:Linoleyl alcohol
4195:Myristyl alcohol
4022:Propylene glycol
3969:Propylene glycol
3883:
3882:
3865:Triphenylethanol
3778:Pirkle's alcohol
3763:Diphenylmethanol
3666:Vanillyl alcohol
3636:Perillyl alcohol
3616:Furfuryl alcohol
3606:Cinnamyl alcohol
3464:1-Dotriacontanol
3116:2-Methoxyethanol
3006:
3005:
2874:alcoholic drinks
2868:
2867:
2850:
2843:
2836:
2827:
2826:
2813:
2812:
2811:
2801:
2800:
2799:
2789:
2788:
2787:
2776:
2775:
2723:Organic compound
2623:Chemical formula
2528:Dihydroxyacetone
2476:Hydrogen cyanide
2161:Cyanodiacetylene
2015:Propadienylidene
1909:Thioformaldehyde
1784:Titanium dioxide
1749:Sodium hydroxide
1670:Hydrogen sulfide
1658:Hydrogen cyanide
1618:Carbonyl sulfide
1583:
1574:
1565:
1523:Silicon monoxide
1456:Hydroxyl radical
1368:
1367:
1348:
1341:
1334:
1325:
1324:
1318:
1317:
1281:
1279:
1278:
1268:
1266:
1265:
1253:
1244:
1243:
1241:
1232:(2): L207–L210.
1219:
1217:
1216:
1202:
1193:
1192:
1190:
1188:
1173:
1167:
1166:
1141:
1135:
1134:
1106:
1100:
1099:
1090:(9): 4073–4074.
1077:
1071:
1070:
1023:
1017:
1016:
984:Nature Chemistry
974:
968:
967:
938:
932:
931:
929:
928:
917:
911:
910:
895:(2nd ed.).
885:
879:
878:
855:
816:
814:
813:
805:
804:
751:
714:
571:The uncatalyzed
551:
536:
528:
517:
472:
417:
411:
408:
407:
350:Chemical formula
273:
272:
257:
255:
239:
219:
208:
197:
186:
175:
155:
135:
111:
34:
30:
26:
4949:
4948:
4944:
4943:
4942:
4940:
4939:
4938:
4929:Vinyl compounds
4914:
4913:
4912:
4907:
4889:
4839:Glycol cleavage
4812:
4808:Ziegler process
4759:
4741:2-Fluoroethanol
4717:
4681:
4665:
4661:Ethylene glycol
4646:1,5-Pentanediol
4625:
4613:
4607:
4580:
4574:
4527:
4510:
4474:Glycylglycitols
4469:
4457:
4451:
4439:
4433:
4429:
4419:
4409:
4399:
4389:
4379:
4369:
4359:
4349:
4339:
4329:
4319:
4314:Ethylene glycol
4309:
4297:
4293:
4276:
4227:
4225:
4219:
4170:
4164:
4136:
4079:
4075:
4065:
4051:
4041:
4027:
4013:
4008:Ethylene glycol
4003:Pentaerythritol
3989:
3973:
3964:Ethylene glycol
3952:
3948:
3938:
3928:
3918:
3908:
3898:
3879:Hydric alcohols
3874:
3792:
3786:
3688:1-Phenylethanol
3681:
3675:
3656:Salicyl alcohol
3621:Isoamyl alcohol
3577:
3528:1-Tetracontanol
3521:
3517:
3513:
3511:
3505:
3446:
3442:
3438:
3436:
3430:
3369:
3365:
3361:
3359:
3353:
3291:
3287:
3283:
3281:
3275:
3222:
3218:
3214:
3212:
3206:
3175:
3171:Tribromoethanol
3106:2-Fluoroethanol
3101:2-Ethoxyethanol
3096:2-Chloroethanol
3091:2-Butoxyethanol
3047:
3033:Methoxymethanol
2999:
2988:
2965:
2938:Medical alcohol
2932:
2897:Isoamyl alcohol
2873:
2859:
2854:
2824:
2819:
2809:
2807:
2797:
2795:
2785:
2783:
2763:
2589:
2565:
2556:
2509:
2499:
2442:
2430:
2411:Propionaldehyde
2386:Ethylene glycol
2375:
2367:
2363:
2334:
2332:
2325:
2281:Cyanohexatriyne
2267:
2260:
2207:
2200:
2135:
2128:
2088:
2041:
2034:
2005:Methoxy radical
1935:
1928:
1924:Thiocyanic acid
1805:
1798:
1708:
1648:Ethynyl radical
1584:
1578:
1577:
1576:
1575:
1569:
1568:
1567:
1566:
1557:
1548:Sulfur monoxide
1533:Sodium chloride
1518:Silicon carbide
1425:Diatomic carbon
1415:Carbon monoxide
1357:
1352:
1322:
1321:
1277:
1274:
1273:
1272:
1270:
1264:
1261:
1260:
1259:
1257:
1254:
1247:
1215:
1212:
1211:
1210:
1208:
1203:
1196:
1186:
1184:
1174:
1170:
1142:
1138:
1131:
1107:
1103:
1078:
1074:
1024:
1020:
980:
975:
971:
939:
935:
926:
924:
918:
914:
907:
886:
882:
876:
856:
849:
844:
812:
809:
808:
807:
803:
800:
799:
798:
796:
786:molecular cloud
782:
775:
771:
762:metal complexes
758:
745:
739:
735:
727:
721:
717:
713:
707:
703:
696:
671:
664:
653:
646:
634:
632:
623:
621:
612:
605:
549:
545:
541:
534:
530:
526:
522:
499:
491:ethylene glycol
483:
466:
457:
436:
429:
424:
423:
422: ?)
413:
409:
405:
401:
385:
362:
358:
352:
338:
335:
330:
329:
318:
315:
314:
311:
305:
304:
298:
297:
294:
288:
287:
276:
258:
251:
242:
222:
209:
178:
158:
138:
125:
114:
101:
87:
85:
84:Hydroxyethylene
83:
75:
74:
25:
12:
11:
5:
4947:
4937:
4936:
4931:
4926:
4909:
4908:
4906:
4905:
4894:
4891:
4890:
4888:
4887:
4882:
4877:
4872:
4870:carbonyl group
4863:
4858:
4853:
4848:
4843:
4842:
4841:
4831:
4826:
4820:
4818:
4814:
4813:
4811:
4810:
4805:
4796:
4787:
4785:Ether cleavage
4782:
4777:
4767:
4765:
4761:
4760:
4758:
4757:
4752:
4750:-butyl alcohol
4743:
4738:
4733:
4727:
4725:
4723:Fluoroalcohols
4719:
4718:
4716:
4715:
4710:
4705:
4700:
4695:
4689:
4687:
4683:
4682:
4680:
4679:
4673:
4671:
4667:
4666:
4664:
4663:
4658:
4653:
4648:
4643:
4641:1,4-Butanediol
4637:
4635:
4631:
4630:
4627:
4626:
4624:
4623:
4617:
4615:
4609:
4608:
4606:
4605:
4600:
4595:
4590:
4584:
4582:
4576:
4575:
4573:
4572:
4567:
4562:
4557:
4552:
4547:
4542:
4537:
4531:
4529:
4520:
4516:
4515:
4512:
4511:
4509:
4508:
4503:
4501:Maltotetraitol
4498:
4493:
4488:
4483:
4477:
4475:
4471:
4470:
4468:
4467:
4461:
4459:
4453:
4452:
4450:
4449:
4443:
4441:
4435:
4434:
4432:
4431:
4427:
4421:
4417:
4411:
4407:
4401:
4397:
4391:
4387:
4381:
4377:
4371:
4367:
4361:
4357:
4351:
4347:
4341:
4337:
4331:
4327:
4321:
4317:
4311:
4307:
4300:
4298:
4295:
4291:
4284:
4282:Sugar alcohols
4278:
4277:
4275:
4274:
4269:
4264:
4259:
4254:
4249:
4244:
4242:Erucyl alcohol
4239:
4233:
4231:
4229:fatty alcohols
4221:
4220:
4218:
4217:
4212:
4207:
4202:
4197:
4192:
4190:Lauryl alcohol
4187:
4182:
4176:
4174:
4172:fatty alcohols
4166:
4165:
4163:
4162:
4157:
4152:
4150:Benzyl alcohol
4146:
4144:
4138:
4137:
4135:
4134:
4129:
4124:
4119:
4114:
4109:
4104:
4099:
4093:
4091:
4085:
4084:
4081:
4080:
4078:
4077:
4073:
4067:
4063:
4053:
4049:
4043:
4039:
4029:
4025:
4015:
4011:
4005:
3999:
3997:
3991:
3990:
3988:
3987:
3981:
3979:
3975:
3974:
3972:
3971:
3966:
3960:
3958:
3954:
3953:
3951:
3950:
3946:
3940:
3936:
3930:
3926:
3920:
3916:
3910:
3906:
3900:
3896:
3889:
3887:
3880:
3876:
3875:
3873:
3872:
3867:
3862:
3860:-Butyl alcohol
3854:
3846:
3844:-butyl alcohol
3837:
3835:Methylpentynol
3832:
3827:
3822:
3817:
3812:
3807:
3802:
3796:
3794:
3788:
3787:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3683:
3677:
3676:
3674:
3673:
3668:
3663:
3658:
3653:
3648:
3643:
3638:
3633:
3628:
3623:
3618:
3613:
3611:Crotyl alcohol
3608:
3603:
3601:Benzyl alcohol
3598:
3596:Anisyl alcohol
3593:
3588:
3586:2-Ethylhexanol
3582:
3579:
3578:
3576:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3524:
3522:
3519:
3515:
3510:Straight-chain
3507:
3506:
3504:
3503:
3498:
3493:
3488:
3483:
3478:
3472:
3467:
3461:
3456:
3453:1-Triacontanol
3449:
3447:
3444:
3440:
3435:Straight-chain
3432:
3431:
3429:
3428:
3423:
3417:
3415:1-Heptacosanol
3412:
3406:
3404:1-Pentacosanol
3401:
3398:1-Tetracosanol
3395:
3390:
3384:
3382:1-Heneicosanol
3379:
3372:
3370:
3367:
3363:
3358:Straight-chain
3355:
3354:
3352:
3351:
3346:
3340:
3338:1-Heptadecanol
3335:
3329:
3327:1-Pentadecanol
3324:
3321:1-Tetradecanol
3318:
3313:
3307:
3301:
3294:
3292:
3289:
3285:
3280:Straight-chain
3277:
3276:
3274:
3273:
3267:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3225:
3223:
3220:
3216:
3211:Straight-chain
3208:
3207:
3205:
3204:
3196:
3191:
3185:
3183:
3177:
3176:
3174:
3173:
3168:
3166:Phenoxyethanol
3163:
3155:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3088:
3083:
3078:
3073:
3068:
3063:
3061:1-Aminoethanol
3057:
3055:
3049:
3048:
3046:
3045:
3040:
3035:
3030:
3025:
3020:
3014:
3012:
3003:
2994:
2993:
2990:
2989:
2987:
2986:
2981:
2975:
2973:
2971:Toxic alcohols
2967:
2966:
2964:
2963:
2962:
2961:
2953:
2951:Methylpentynol
2948:
2942:
2940:
2934:
2933:
2931:
2930:
2925:
2923:-Butyl alcohol
2917:
2909:
2904:
2899:
2894:
2889:
2884:
2878:
2876:
2865:
2864:By consumption
2861:
2860:
2853:
2852:
2845:
2838:
2830:
2821:
2820:
2818:
2817:
2805:
2793:
2781:
2768:
2765:
2764:
2762:
2761:
2756:
2751:
2746:
2740:
2735:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2648:Cosmochemistry
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2613:Astrochemistry
2610:
2605:
2599:
2597:
2591:
2590:
2588:
2587:
2582:
2577:
2572:
2567:
2563:
2559:
2554:
2550:
2545:
2540:
2535:
2530:
2525:
2519:
2517:
2511:
2510:
2508:
2507:
2502:
2497:
2493:
2488:
2483:
2478:
2473:
2468:
2466:Formyl radical
2463:
2458:
2452:
2446:
2444:
2436:
2435:
2432:
2431:
2429:
2428:
2423:
2418:
2413:
2408:
2403:
2398:
2396:Methyl acetate
2393:
2388:
2383:
2378:
2373:
2369:
2365:
2361:
2355:
2350:
2345:
2339:
2337:
2327:
2326:
2324:
2323:
2318:
2313:
2308:
2303:
2298:
2293:
2288:
2286:Dimethyl ether
2283:
2278:
2272:
2270:
2262:
2261:
2259:
2258:
2253:
2251:Methyl formate
2248:
2243:
2238:
2236:Glycolaldehyde
2233:
2228:
2223:
2218:
2212:
2210:
2202:
2201:
2199:
2198:
2193:
2188:
2183:
2178:
2173:
2171:Glycolonitrile
2168:
2166:Ethylene oxide
2163:
2158:
2157:
2156:
2146:
2140:
2138:
2130:
2129:
2127:
2126:
2121:
2116:
2111:
2106:
2101:
2096:
2091:
2086:
2082:
2077:
2072:
2067:
2065:Cyclopropenone
2062:
2057:
2052:
2046:
2044:
2036:
2035:
2033:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1965:Cyanoacetylene
1962:
1957:
1952:
1947:
1940:
1938:
1930:
1929:
1927:
1926:
1921:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1884:Methyl radical
1881:
1876:
1871:
1866:
1861:
1859:Isocyanic acid
1856:
1851:
1846:
1841:
1836:
1831:
1826:
1824:Isocyanic acid
1821:
1816:
1810:
1808:
1800:
1799:
1797:
1796:
1791:
1786:
1781:
1776:
1771:
1769:Sulfur dioxide
1766:
1761:
1756:
1751:
1746:
1744:Sodium cyanide
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1702:
1697:
1692:
1687:
1682:
1677:
1672:
1667:
1661:
1655:
1653:Formyl radical
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1613:Carbon dioxide
1610:
1605:
1600:
1594:
1592:
1586:
1585:
1560:
1558:
1556:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1494:
1489:
1484:
1478:
1473:
1468:
1463:
1461:Iron(II) oxide
1458:
1453:
1447:
1442:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1387:
1382:
1376:
1374:
1365:
1359:
1358:
1351:
1350:
1343:
1336:
1328:
1320:
1319:
1275:
1262:
1245:
1239:10.1086/324762
1213:
1194:
1168:
1136:
1130:978-3527306732
1129:
1101:
1072:
1018:
991:(6): 443−448.
978:
969:
933:
912:
905:
880:
874:
846:
845:
843:
840:
827:unimolecularly
819:ethylene oxide
810:
801:
781:
778:
773:
769:
757:
754:
753:
752:
741:
737:
733:
723:
719:
715:
709:
705:
704:=CHOAc → (CH
701:
670:
667:
662:
651:
644:
630:
628:
619:
617:
610:
603:
565:Wacker process
553:
552:
547:
543:
532:
524:
519:
518:
498:
495:
489:of water from
482:
479:
464:
441:, also called
434:
431:
430:
425:
403:
402:
398:standard state
395:
392:
391:
386:
383:
380:
379:
375:
374:
371:
365:
364:
360:
356:
353:
348:
345:
344:
340:
339:
337:
336:
333:
325:
324:
323:
320:
319:
317:
316:
312:
309:
308:
306:
302:
301:
299:
295:
292:
291:
283:
282:
281:
278:
277:
275:
274:
261:
259:
247:
244:
243:
241:
240:
232:
230:
224:
223:
221:
220:
212:
210:
202:
199:
198:
188:
180:
179:
177:
176:
168:
166:
160:
159:
157:
156:
148:
146:
140:
139:
137:
136:
128:
126:
119:
116:
115:
113:
112:
104:
102:
97:
94:
93:
89:
88:
81:
77:
76:
72:
71:
65:
64:
60:
59:
56:
55:
45:
28:Vinyl alcohol
9:
6:
4:
3:
2:
4946:
4935:
4932:
4930:
4927:
4925:
4922:
4921:
4919:
4904:
4896:
4895:
4892:
4886:
4883:
4881:
4878:
4876:
4873:
4871:
4867:
4864:
4862:
4859:
4857:
4854:
4852:
4849:
4847:
4844:
4840:
4837:
4836:
4835:
4832:
4830:
4827:
4825:
4824:Deprotonation
4822:
4821:
4819:
4815:
4809:
4806:
4804:
4800:
4797:
4795:
4791:
4788:
4786:
4783:
4781:
4778:
4776:
4772:
4769:
4768:
4766:
4762:
4756:
4753:
4751:
4749:
4744:
4742:
4739:
4737:
4734:
4732:
4729:
4728:
4726:
4724:
4720:
4714:
4711:
4709:
4706:
4704:
4701:
4699:
4696:
4694:
4691:
4690:
4688:
4684:
4678:
4675:
4674:
4672:
4668:
4662:
4659:
4657:
4654:
4652:
4649:
4647:
4644:
4642:
4639:
4638:
4636:
4632:
4622:
4619:
4618:
4616:
4610:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4585:
4583:
4579:Sesquiterpene
4577:
4571:
4568:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4543:
4541:
4538:
4536:
4533:
4532:
4530:
4524:
4521:
4517:
4507:
4504:
4502:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4479:
4478:
4476:
4472:
4466:
4463:
4462:
4460:
4454:
4448:
4445:
4444:
4442:
4436:
4425:
4422:
4415:
4412:
4405:
4402:
4395:
4392:
4385:
4382:
4375:
4372:
4365:
4362:
4355:
4352:
4345:
4342:
4335:
4332:
4325:
4322:
4315:
4312:
4305:
4302:
4301:
4299:
4288:
4285:
4283:
4279:
4273:
4270:
4268:
4265:
4263:
4260:
4258:
4257:Oleyl alcohol
4255:
4253:
4250:
4248:
4245:
4243:
4240:
4238:
4235:
4234:
4232:
4230:
4222:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4177:
4175:
4173:
4167:
4161:
4158:
4156:
4153:
4151:
4148:
4147:
4145:
4143:
4139:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4103:
4100:
4098:
4095:
4094:
4092:
4090:
4089:Amyl alcohols
4086:
4071:
4068:
4061:
4057:
4054:
4047:
4044:
4037:
4033:
4030:
4023:
4019:
4016:
4009:
4006:
4004:
4001:
4000:
3998:
3996:
3992:
3986:
3983:
3982:
3980:
3976:
3970:
3967:
3965:
3962:
3961:
3959:
3955:
3944:
3943:Cetyl alcohol
3941:
3934:
3931:
3924:
3921:
3914:
3911:
3904:
3901:
3894:
3891:
3890:
3888:
3884:
3881:
3877:
3871:
3868:
3866:
3863:
3861:
3859:
3855:
3853:
3852:-Amyl alcohol
3851:
3847:
3845:
3843:
3838:
3836:
3833:
3831:
3830:Ethchlorvynol
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3803:
3801:
3798:
3797:
3795:
3793:alcohols (3°)
3789:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3758:Cyclopropanol
3756:
3754:
3753:Cyclopentanol
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3682:alcohols (2°)
3678:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3591:Allyl alcohol
3589:
3587:
3584:
3583:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3525:
3523:
3508:
3502:
3499:
3497:
3494:
3492:
3489:
3487:
3484:
3482:
3479:
3476:
3473:
3471:
3468:
3465:
3462:
3460:
3457:
3454:
3451:
3450:
3448:
3433:
3427:
3426:1-Nonacosanol
3424:
3421:
3420:1-Octacosanol
3418:
3416:
3413:
3410:
3409:1-Hexacosanol
3407:
3405:
3402:
3399:
3396:
3394:
3391:
3388:
3385:
3383:
3380:
3377:
3374:
3373:
3371:
3356:
3350:
3349:1-Nonadecanol
3347:
3344:
3343:1-Octadecanol
3341:
3339:
3336:
3333:
3332:1-Hexadecanol
3330:
3328:
3325:
3322:
3319:
3317:
3314:
3311:
3308:
3305:
3302:
3299:
3296:
3295:
3293:
3278:
3271:
3268:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3226:
3224:
3209:
3203:
3201:
3197:
3195:
3192:
3190:
3187:
3186:
3184:
3182:
3178:
3172:
3169:
3167:
3164:
3162:
3160:
3156:
3154:
3152:
3148:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3079:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3058:
3056:
3054:
3050:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3023:Aminomethanol
3021:
3019:
3016:
3015:
3013:
3011:
3007:
3004:
3001:
2995:
2985:
2982:
2980:
2977:
2976:
2974:
2972:
2968:
2960:
2957:
2956:
2954:
2952:
2949:
2947:
2946:Ethchlorvynol
2944:
2943:
2941:
2939:
2935:
2929:
2926:
2924:
2922:
2918:
2916:
2915:-Amyl alcohol
2914:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2879:
2877:
2875:
2869:
2866:
2862:
2858:
2851:
2846:
2844:
2839:
2837:
2832:
2831:
2828:
2816:
2806:
2804:
2794:
2792:
2782:
2780:
2779:
2770:
2769:
2766:
2760:
2757:
2755:
2752:
2750:
2747:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2678:Homochirality
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2600:
2598:
2596:
2592:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2566:
2560:
2558:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2533:Methoxyethane
2531:
2529:
2526:
2524:
2521:
2520:
2518:
2516:
2512:
2506:
2503:
2501:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2456:
2453:
2451:
2448:
2447:
2445:
2441:
2437:
2427:
2424:
2422:
2419:
2417:
2416:Butyronitrile
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2391:Ethyl formate
2389:
2387:
2384:
2382:
2379:
2377:
2370:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2340:
2338:
2336:
2328:
2322:
2319:
2317:
2316:Propionitrile
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2273:
2271:
2269:
2263:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2213:
2211:
2209:
2203:
2197:
2196:Vinyl alcohol
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2155:
2154:Vinyl cyanide
2152:
2151:
2150:
2149:Acrylonitrile
2147:
2145:
2142:
2141:
2139:
2137:
2131:
2125:
2122:
2120:
2117:
2115:
2114:Pentynylidyne
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2047:
2045:
2043:
2037:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2010:Methylenimine
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1945:
1942:
1941:
1939:
1937:
1931:
1925:
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1890:
1889:Propynylidyne
1887:
1885:
1882:
1880:
1879:Methyl cation
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1839:Fulminic acid
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1811:
1809:
1807:
1801:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1715:
1714:Nitrous oxide
1712:
1710:
1703:
1701:
1698:
1696:
1693:
1691:
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1671:
1668:
1665:
1662:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1608:Amino radical
1606:
1604:
1601:
1599:
1596:
1595:
1593:
1591:
1587:
1582:
1573:
1564:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1538:Sodium iodide
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1498:
1495:
1493:
1490:
1488:
1485:
1482:
1479:
1477:
1474:
1472:
1469:
1467:
1464:
1462:
1459:
1457:
1454:
1451:
1448:
1446:
1443:
1441:
1438:
1436:
1433:
1431:
1428:
1426:
1423:
1421:
1420:Cyano radical
1418:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1400:Carbon cation
1398:
1396:
1393:
1391:
1388:
1386:
1383:
1381:
1378:
1377:
1375:
1373:
1369:
1366:
1364:
1360:
1356:
1349:
1344:
1342:
1337:
1335:
1330:
1329:
1326:
1315:
1311:
1307:
1303:
1299:
1295:
1291:
1287:
1286:
1252:
1250:
1240:
1235:
1231:
1227:
1226:
1221:
1201:
1199:
1183:
1179:
1172:
1164:
1160:
1157:(8): 2483–6.
1156:
1152:
1151:
1146:
1145:Cotton, F. A.
1140:
1132:
1126:
1122:
1118:
1114:
1113:
1105:
1097:
1093:
1089:
1085:
1084:
1076:
1068:
1064:
1060:
1056:
1052:
1048:
1044:
1040:
1036:
1032:
1031:
1022:
1014:
1010:
1006:
1002:
998:
994:
990:
986:
985:
973:
965:
961:
957:
953:
949:
946:
945:
937:
923:
916:
908:
902:
898:
894:
890:
884:
877:
871:
867:
866:
861:
854:
852:
847:
839:
837:
832:
828:
824:
820:
794:
790:
789:Sagittarius B
787:
777:
767:
763:
749:
744:
731:
726:
716:
712:
699:
695:
694:
693:
691:
687:
683:
682:vinyl acetate
679:
676:
675:thermoplastic
666:
661:
657:
650:
642:
638:
627:
616:
609:
602:
598:
594:
589:
585:
583:
582:Carbonic acid
578:
574:
566:
562:
557:
540:
539:
538:
516:
512:
511:
510:
508:
504:
494:
492:
488:
478:
476:
470:
463:
460:
456:
452:
448:
444:
440:
439:Vinyl alcohol
428:
421:
416:
399:
393:
390:
389:Allyl alcohol
387:
382:
381:
376:
372:
370:
367:
366:
354:
351:
347:
346:
341:
332:
331:
328:
321:
307:
300:
290:
289:
286:
279:
271:
267:
266:DTXSID8051467
263:
262:
260:
250:
246:
245:
238:
234:
233:
231:
229:
226:
225:
218:
214:
213:
211:
205:
201:
200:
196:
192:
189:
187:
185:ECHA InfoCard
182:
181:
174:
170:
169:
167:
165:
162:
161:
154:
150:
149:
147:
145:
142:
141:
134:
130:
129:
127:
123:
118:
117:
110:
106:
105:
103:
100:
96:
95:
90:
82:Hydroxyethene
78:
70:
66:
61:
50:
46:
40:
36:
35:
31:
23:
19:
4771:Substitution
4764:Preparations
4747:
4713:Stigmasterol
4708:β-Sitosterol
4506:Polyglycitol
4496:Maltotriitol
4456:Cyclic sugar
4224:Branched and
4132:Pentan-3-ol
4127:Pentan-2-ol
4122:Pentan-1-ol
3857:
3849:
3841:
3748:Cyclohexanol
3400:(lignoceryl)
3393:1-Tricosanol
3316:1-Tridecanol
3272:(pelargonic)
3199:
3158:
3150:
3146:
3141:Ethanolamine
2920:
2912:
2771:
2754:Spectroscopy
2608:Astrobiology
2461:Formaldehyde
2353:Benzonitrile
2195:
2144:Acetaldehyde
2099:Methanethiol
2050:Acetonitrile
1955:Carbodiimide
1834:Formaldehyde
1829:Cyanoethynyl
1680:Iron cyanide
1675:Hydroperoxyl
1476:Nitric oxide
1289:
1285:ChemPhysChem
1283:
1229:
1223:
1187:December 20,
1185:. Retrieved
1171:
1154:
1148:
1139:
1110:
1104:
1087:
1081:
1075:
1034:
1028:
1021:
988:
982:
972:
947:
942:
936:
925:. Retrieved
915:
892:
883:
864:
860:March, Jerry
783:
759:
747:
742:
729:
724:
710:
697:
684:followed by
672:
659:
648:
625:
614:
607:
600:
590:
586:
570:
561:acetaldehyde
546:C=CHOH → H
520:
507:acetaldehyde
503:tautomerizes
500:
484:
475:acetaldehyde
446:
442:
438:
437:
92:Identifiers
80:Other names
4829:Protonation
4746:Nonafluoro-
4693:Cholesterol
4670:Trialcohols
4540:Citronellol
4526:Monoterpene
4438:Deoxy sugar
4226:unsaturated
3913:Isopropanol
3840:Nonafluoro-
3768:Isopropanol
3387:1-Docosanol
3378:(arachidyl)
3310:1-Dodecanol
3304:1-Undecanol
2728:Outer space
2638:Cosmic dust
2603:Abiogenesis
2515:Unconfirmed
2471:Heavy water
2311:Ethanethiol
2226:Cyanoallene
2216:Acetic acid
2186:Methylamine
2070:Diacetylene
1985:Formic acid
1975:Cyanomethyl
1633:Diazenylium
1623:CCP radical
1499:(molecular)
1483:(molecular)
1452:(molecular)
756:As a ligand
641:heavy water
487:elimination
453:. With the
343:Properties
191:100.008.350
153:ChEMBL76101
4918:Categories
4790:Hydrolysis
4775:haloalkane
4703:Lanosterol
4698:Ergosterol
4634:Dialcohols
4603:Patchoulol
4404:Galactitol
4334:Erythritol
4210:Tridecanol
4032:Erythritol
3933:1-Pentanol
3743:3-Pentanol
3738:2-Pentanol
3708:3-Heptanol
3703:2-Heptanol
3661:Tryptophol
3466:(lacceryl)
3376:1-Icosanol
3323:(myristyl)
3306:(hendecyl)
3259:1-Heptanol
3249:1-Pentanol
3239:1-Propanol
3194:Isobutanol
2928:Tryptophol
2902:Isobutanol
2882:1-Propanol
2643:Cosmic ray
2585:Silylidyne
2548:Hemolithin
2523:Anthracene
2440:Deuterated
2421:Pyrimidine
2231:Ethanimine
2094:Ketenimine
1950:Butadiynyl
1774:Thioformyl
1628:Chloronium
927:2014-08-30
842:References
686:hydrolysis
595:-produced
369:Molar mass
237:GO1N1ZPR3B
164:ChemSpider
120:3D model (
99:CAS Number
4817:Reactions
4799:Hydration
4612:Diterpene
4598:Nerolidol
4588:Bisabolol
4570:Terpineol
4424:Volemitol
4215:Undecanol
4169:Saturated
4070:Volemitol
3923:1-Butanol
3733:2-Octanol
3728:2-Nonanol
3718:3-Hexanol
3713:2-Hexanol
3693:2-Butanol
3680:Secondary
3512:saturated
3437:saturated
3389:(behenyl)
3360:saturated
3345:(stearyl)
3298:1-Decanol
3282:saturated
3270:1-Nonanol
3264:1-Octanol
3254:1-Hexanol
3244:1-Butanol
3213:saturated
2575:Phosphine
2443:molecules
2376:fullerene
2276:Acetamide
2080:Formamide
1960:Cyanamide
1814:Acetylene
1789:Tricarbon
1700:Methylene
1685:Isoformyl
1590:Triatomic
1363:Molecules
1314:233447839
736:O → (CH
656:half-life
593:deuterium
481:Synthesis
447:ethylenol
86:Ethylenol
4903:Category
4677:Glycerol
4614:alcohols
4593:Farnesol
4581:alcohols
4565:Rhodinol
4550:Linalool
4545:Geraniol
4528:alcohols
4486:Lactitol
4481:Maltitol
4465:Inositol
4458:alcohols
4440:alcohols
4394:Sorbitol
4384:Mannitol
4354:Arabitol
4344:Threitol
4324:Glycerol
4060:Sorbitol
4056:Mannitol
4036:Threitol
4018:Glycerol
3985:Glycerol
3893:Methanol
3791:Tertiary
3477:(geddyl)
3312:(lauryl)
3300:(capric)
3266:(capryl)
3229:Methanol
3202:-Butanol
3010:Methanol
3000:alcohols
2984:Methanol
2857:Alcohols
2562:Linear C
2543:Graphene
2455:Ammonium
2256:Acrolein
2119:Propynal
2104:Methanol
2075:Ethylene
1944:Ammonium
1719:Nitroxyl
1543:Sulfanyl
1487:Imidogen
1481:Nitrogen
1450:Hydrogen
1395:Argonium
1372:Diatomic
1306:33913232
1067:42079807
1059:22903524
1013:21602858
964:19834921
862:(2007),
760:Several
613:= 4.75,
363:O
109:557-75-5
4794:epoxide
4686:Sterols
4555:Menthol
4535:Borneol
4491:Isomalt
4447:Fucitol
4374:Xylitol
4364:Ribitol
4205:Octanol
4200:Nonanol
4185:Decanol
4046:Xylitol
3903:Ethanol
3411:(ceryl)
3234:Ethanol
3181:Butanol
3136:Ethanol
3053:Ethanol
2998:Primary
2959:Ethanol
2892:Ethanol
2708:Kerogen
2595:Related
2538:Glycine
2491:Propyne
2450:Ammonia
2348:Benzene
2343:Acetone
2335:or more
2306:Propene
2291:Ethanol
2181:Propyne
2000:Methane
1869:Ketenyl
1819:Ammonia
1280:CCH(OH)
1039:Bibcode
1030:Science
993:Bibcode
793:isomers
776:OH)Cl.
722:−CHOAc)
708:−CHOAc)
688:of the
455:formula
443:ethenol
420:what is
418: (
204:PubChem
73:Ethenol
22:ethynol
18:ethanol
4803:alkene
4621:Phytol
4414:Iditol
3646:Prenol
2759:Tholin
2580:Pyrene
2025:Silane
1995:Ketene
1497:Oxygen
1312:
1304:
1127:
1065:
1057:
1011:
962:
903:
872:
766:ligand
740:−CHOH)
637:ketene
550:CC(O)H
535:C=CHOH
527:CC(O)H
415:verify
412:
327:SMILES
144:ChEMBL
63:Names
4924:Enols
4560:Nerol
2745:(PAH)
2333:atoms
2268:atoms
2208:atoms
2206:Eight
2136:atoms
2134:Seven
2042:atoms
1936:atoms
1806:atoms
1794:Water
1724:Ozone
1666:(HNC)
1660:(HCN)
1310:S2CID
1218:=CHOH
1063:S2CID
690:ester
505:) to
285:InChI
217:11199
173:10726
122:JSmol
4748:tert
3858:tert
3850:tert
3842:tert
3002:(1°)
2921:tert
2913:tert
2266:Nine
1934:Five
1844:HCCN
1804:Four
1764:SiNC
1302:PMID
1189:2006
1125:ISBN
1055:PMID
1009:PMID
960:PMID
901:ISBN
870:ISBN
750:HOAc
451:enol
334:OC=C
228:UNII
4868:of
4801:of
4792:of
4773:of
4294:— C
3518:— C
3443:— C
3366:— C
3288:— C
3219:— C
2557:NCO
2457:ion
2364:, C
2331:Ten
2040:Six
1946:ion
1294:doi
1267:CHO
1234:doi
1230:561
1159:doi
1117:doi
1092:doi
1088:100
1047:doi
1035:337
1001:doi
952:doi
795:of
718:(CH
663:1/2
254:EPA
207:CID
20:or
4920::
4426:(C
4416:(C
4406:(C
4396:(C
4386:(C
4376:(C
4366:(C
4356:(C
4346:(C
4336:(C
4326:(C
4316:(C
4306:(C
4072:(C
4062:(C
4058:,
4048:(C
4038:(C
4034:,
4024:(C
4020:,
4010:(C
3947:16
3945:(C
3935:(C
3925:(C
3915:(C
3905:(C
3895:(C
3520:49
3516:40
3445:39
3441:30
3368:29
3364:20
3290:19
3286:10
2374:70
2366:60
2362:60
2360:(C
2085:HC
1308:.
1300:.
1290:22
1288:.
1258:CH
1248:^
1228:.
1222:.
1209:CH
1197:^
1155:95
1153:.
1123:.
1086:.
1061:.
1053:.
1045:.
1033:.
1007:.
999:.
987:.
958:.
948:48
850:^
838:.
746:+
728:+
700:CH
643:(D
509::
467:CH
4430:)
4428:7
4420:)
4418:6
4410:)
4408:6
4400:)
4398:6
4390:)
4388:6
4380:)
4378:5
4370:)
4368:5
4360:)
4358:5
4350:)
4348:4
4340:)
4338:4
4330:)
4328:3
4320:)
4318:2
4310:)
4308:1
4296:7
4292:1
4290:C
4076:)
4074:7
4066:)
4064:6
4052:)
4050:5
4042:)
4040:4
4028:)
4026:3
4014:)
4012:2
3949:)
3939:)
3937:5
3929:)
3927:4
3919:)
3917:3
3909:)
3907:2
3899:)
3897:1
3514:C
3439:C
3362:C
3284:C
3221:9
3217:1
3215:C
3200:n
3159:N
3151:N
3149:,
3147:N
2849:e
2842:t
2835:v
2564:5
2555:2
2553:H
2500:D
2498:2
2496:N
2372:C
2089:N
2087:4
1709:H
1707:2
1705:N
1347:e
1340:t
1333:v
1316:.
1296::
1276:2
1271:H
1263:3
1242:.
1236::
1220:"
1214:2
1191:.
1165:.
1161::
1133:.
1119::
1098:.
1094::
1069:.
1049::
1041::
1015:.
1003::
995::
989:3
979:3
966:.
954::
930:.
909:.
815:O
811:4
806:H
802:2
797:C
774:3
772:H
770:2
748:n
743:n
738:2
734:2
732:H
730:n
725:n
720:2
711:n
706:2
702:2
698:n
660:t
652:t
649:k
645:2
633:O
631:2
629:D
626:k
624:/
622:O
620:2
618:H
615:k
611:D
608:k
606:/
604:H
601:k
599:(
563:(
548:3
544:2
542:H
533:2
531:H
525:3
523:H
471:H
469:O
465:2
462:H
459:C
410:Y
361:4
359:H
357:2
355:C
256:)
252:(
124:)
24:.
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