358:
219:
36:
628:
633:
618:
623:
856:
860:
27:
1061:
861:
859:
641:
1203:
at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of
598:
877:
771:
862:
763:
1962:
1690:
1628:
988:
2021:
1991:
1969:
1074:
1715:
1897:
Yoffe, David; Frim, Ron; Ukeles, Shmuel D.; Dagani, Michael J.; Barda, Henry J.; Benya, Theodore J.; Sanders, David C. (2013). "Bromine
Compounds".
1973:
407:
1806:
Lemar, Katey M.; Passa, Ourania; Aon, Miguel A.; Cortassa, Sonia; Müller, Carsten T.; Plummer, Sue; O'Rourke, Brian; Lloyd, David (2005).
884:
767:
1951:
1914:
1643:
707:
1069:
1732:
1657:
1870:
1127:, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a
372:
870:
1986:
1930:
1081:
1371:
1344:
579:
1575:. It is significantly more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a
701:
305:
214:
1348:
632:
1713:
Ludger Krähling; Jürgen Krey; Gerald
Jakobson; Johann Grolig; Leopold Miksche (2002). "Allyl Compounds".
1336:
336:
176:
751:
35:
1375:
1364:
1012:
999:
627:
538:
755:
2006:
226:
2011:
907:
823:
353:
1784:
561:
617:
136:
1403:
196:
2016:
1549:
1447:
1423:
1395:
1128:
719:
655:
610:
799:
795:
622:
314:
48:
1043:
779:
118:
8:
1871:"Studies on the effect of some eradicants on mycorrhizal development in forest nurseries"
1143:
1124:
94:
84:
1778:
357:
218:
156:
26:
1846:
1807:
1407:
1109:
727:
1712:
1910:
1851:
1833:
1750:
1728:
1653:
1588:
1415:
1411:
1324:
1159:
1037:
803:
1902:
1841:
1823:
1759:
1720:
1360:
1155:
1105:
517:
430:
1906:
1356:
1332:
1281:
1196:
920:
739:
278:
715:
1808:"Allyl alcohol and garlic (Allium sativum) extract produce oxidative stress in
1340:
1200:
1166:
1052:
827:
731:
528:
1958:
1624:
962:
944:
2000:
1837:
1763:
1724:
1682:
1568:
1489:
1313:
1274:
1208:
743:
506:
496:
207:
1855:
1383:
1136:
1828:
883:
815:
1576:
1572:
1561:
1528:
1387:
1339:. Other methods include carbon-carbon bond-forming reactions such as the
1305:
1301:
1285:
1162:
1132:
896:
783:
1265:
Hydrolysis of this acetate gives allyl alcohol. In alternative fashion,
869:
787:
759:
1565:
1542:
1379:
1097:
876:
775:
455:
227:
187:
811:
1649:
1482:
1474:
1467:
1317:
1266:
1204:
325:
1051:
Except where otherwise noted, data are given for materials in their
1553:
1451:
1443:
1309:
1297:
1270:
842:
253:
1956:
1622:
835:
117:
1537:
1463:
1427:
1399:
1131:
to many specialized compounds such as flame-resistant materials,
735:
486:
265:
661:
1557:
1419:
1391:
747:
167:
1488:
Allyl alcohol is the precursor in the commercial synthesis of
689:
1687:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1546:
1459:
1455:
1431:
1355:
is another route. Some of these methods are achieved by the
1352:
1328:
1140:
807:
289:
147:
107:
1783:(2nd ed.). London: Macmillan and Co., Limited. p.
711:
341:
1478:
1025:
681:
476:
244:
723:
1532:
1748:
Oliver Kamm & C. S. Marvel (1941). "Allyl alcohol".
1394:
cloves (producing from garlic in two ways: firstly by a
693:
673:
1747:
1195:
Allyl alcohol can also be made by the rearrangement of
1139:. Allyl alcohol is the smallest representative of the
1987:
State of
Michigan public information on allyl alcohol
1963:
National
Institute for Occupational Safety and Health
1896:
1805:
1691:
National
Institute for Occupational Safety and Health
1629:
National
Institute for Occupational Safety and Health
1466:
esters are prepared from allyl alcohol, e.g. diallyl
677:
1641:
669:
135:
1998:
665:
277:
1280:In principle, allyl alcohol can be obtained by
858:
819:
93:
1899:Ullmann's Encyclopedia of Industrial Chemistry
1716:Ullmann's Encyclopedia of Industrial Chemistry
1154:Allyl alcohol is produced commercially by the
831:
685:
1970:Institut national de recherche et de sécurité
1386:. Today a Allyl alcohol can be formed after
1370:Allyl alcohol was first prepared in 1856 by
1323:Allyl alcohols in general are prepared by
791:
356:
217:
195:
2022:Substances discovered in the 19th century
1845:
1827:
1789:Practical Organic Chemistry Cohen Julius.
1708:
1706:
1704:
1702:
1700:
313:
1957:NIOSH Pocket Guide to Chemical Hazards.
1931:"National Technical Information Service"
1868:
1623:NIOSH Pocket Guide to Chemical Hazards.
1019:TWA 2 ppm (5 mg/m) ST 4 ppm (10 mg/m)
1952:International Chemical Safety Card 0095
1618:
1616:
1614:
1612:
1610:
1608:
1606:
1604:
352:
1999:
1697:
915:378 °C (712 °F; 651 K)
208:
1776:
1645:CRC Handbook of Chemistry and Physics
1442:Allyl alcohol is converted mainly to
1312:or glyceric formate, either of which
1291:
511:97 °C (207 °F; 370 K)
384:Key: XXROGKLTLUQVRX-UHFFFAOYSA-N
175:
155:
1801:
1799:
1797:
1635:
1601:
901:21 °C (70 °F; 294 K)
394:Key: XXROGKLTLUQVRX-UHFFFAOYAC
381:InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2
268:
252:
13:
1935:US Environmental Protection Agency
1199:, a reaction that is catalyzed by
854:
391:InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2
14:
2033:
1945:
1862:
1794:
1992:Occupational exposure guidelines
1642:Haynes, William M., ed. (2016).
1059:
631:
626:
621:
616:
442:
34:
25:
1978:Fiche toxicologique n° 156
1923:
1890:
1437:
1055:(at 25 °C , 100 kPa).
1770:
1741:
1675:
1666:
1345:Morita-Baylis-Hillman reaction
580:Occupational safety and health
448:
436:
16:Organic compound (CH2=CHCH2OH)
1:
1907:10.1002/14356007.a04_405.pub2
1594:
1149:
993:(US health exposure limits):
7:
1780:Practical Organic Chemistry
1582:
933:or concentration (LD, LC):
10:
2038:
1365:Mislow-Evans rearrangement
1165:through the hydrolysis of
593:Highly toxic, lachrymator
1522:
1349:Ramberg-Bäcklund reaction
1049:
987:
975:1000 ppm (rabbit, 3.5 hr)
929:
597:
577:
572:
423:
403:
368:
77:
59:
47:
42:
33:
24:
1764:10.15227/orgsyn.001.0015
1725:10.1002/14356007.a01_425
702:Precautionary statements
1719:. Weinheim: Wiley-VCH.
1392:garlic (Allium sativum)
1308:to give (respectively)
977:1000 ppm (monkey, 4 hr)
969:1000 ppm (mammal, 1 hr)
951:80 mg/kg (rat, orally)
562:Magnetic susceptibility
1777:Cohen, Julius (1900).
1672:Allyl alcohol toxicity
1347:, or a variant of the
865:
1829:10.1099/mic.0.28095-0
1550:alcohol dehydrogenase
1477:and can be used as a
1462:. Also, a variety of
1448:chemical intermediate
973:207 ppm (mouse, 2 hr)
864:
1450:in the synthesis of
1414:and secondly by the
979:1060 ppm (rat, 1 hr)
963:median concentration
847:(fire diamond)
49:Preferred IUPAC name
1869:Laiho Mikola, O.P.
1541:, allyl alcohol is
1475:herbicidal activity
1454:, glycidyl ethers,
1408:diallyl trisulphide
1351:. Hydrogenation of
1296:In the laboratory,
1277:gives the alcohol.
1269:can be oxidized to
983:76 ppm (rat, 8 hr)
981:165 ppm (rat, 4 hr)
518:Solubility in water
463: g·mol
21:
1556:, which can cause
1473:Allyl alcohol has
1412:diallyl disulphide
1406:products such as
1292:Laboratory methods
1110:structural formula
1082:Infobox references
1028:(Immediate danger)
971:76 ppm (rat, 8 hr)
866:
19:
1974:Alcool allylique.
1916:978-3-527-30385-4
1901:. pp. 1–31.
1878:helda.helsinki.fi
1822:(10): 3257–3265.
1751:Organic Syntheses
1648:(97th ed.).
1589:Propargyl alcohol
1571:and depletion of
1527:Allyl alcohol is
1396:self-condensation
1337:organic peroxides
1331:compounds, using
1325:allylic oxidation
1090:Chemical compound
1088:
1087:
1038:Safety data sheet
656:Hazard statements
568:-36.70·10 cm/mol
471:colorless liquid
337:CompTox Dashboard
119:Interactive image
2029:
2007:Primary alcohols
1983:
1966:
1939:
1938:
1927:
1921:
1920:
1894:
1888:
1887:
1885:
1884:
1875:
1866:
1860:
1859:
1849:
1831:
1810:Candida albicans
1803:
1792:
1791:
1774:
1768:
1766:
1745:
1739:
1738:
1710:
1695:
1694:
1679:
1673:
1670:
1664:
1663:
1652:. p. 5–88.
1639:
1633:
1632:
1620:
1518:
1361:Wharton reaction
1333:selenium dioxide
1261:
1191:
1182:Cl + NaOH → CH
1122:
1106:organic compound
1072:
1066:
1063:
1062:
921:Explosive limits
886:
879:
872:
857:
837:
833:
829:
825:
821:
817:
813:
809:
805:
801:
797:
793:
789:
785:
781:
777:
773:
769:
765:
761:
757:
753:
749:
745:
741:
737:
733:
729:
725:
721:
717:
713:
709:
695:
691:
687:
683:
679:
675:
671:
667:
663:
635:
630:
625:
620:
462:
450:
444:
438:
431:Chemical formula
361:
360:
345:
343:
317:
281:
270:
256:
229:
221:
210:
199:
179:
159:
139:
121:
97:
38:
29:
22:
18:
2037:
2036:
2032:
2031:
2030:
2028:
2027:
2026:
2012:Allyl compounds
1997:
1996:
1981:
1948:
1943:
1942:
1929:
1928:
1924:
1917:
1895:
1891:
1882:
1880:
1873:
1867:
1863:
1804:
1795:
1775:
1771:
1746:
1742:
1735:
1711:
1698:
1683:"Allyl alcohol"
1681:
1680:
1676:
1671:
1667:
1660:
1640:
1636:
1621:
1602:
1597:
1585:
1525:
1516:
1512:
1508:
1504:
1500:
1496:
1481:eradicant) and
1440:
1372:Auguste Cahours
1357:Luche reduction
1294:
1282:dehydrogenation
1259:
1255:
1251:
1247:
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1215:
1197:propylene oxide
1189:
1185:
1181:
1177:
1173:
1152:
1120:
1116:
1112:
1091:
1084:
1079:
1078:
1077: ?)
1068:
1064:
1060:
1056:
1029:
1016:
1003:
982:
980:
978:
976:
974:
972:
970:
966:
960:
948:
942:
912:
909:
891:
890:
889:
888:
881:
874:
867:
863:
855:
704:
658:
644:
613:
590:
565:
554:
547:
520:
460:
447:
441:
433:
419:
416:
411:
410:
399:
396:
395:
392:
386:
385:
382:
376:
375:
364:
346:
339:
320:
300:
284:
271:
259:
239:
202:
182:
162:
142:
124:
111:
100:
87:
73:
71:
70:Allylic alcohol
69:
67:
65:
63:
55:
54:
17:
12:
11:
5:
2035:
2025:
2024:
2019:
2014:
2009:
1995:
1994:
1989:
1984:
1980:. Paris:INRS.
1967:
1954:
1947:
1946:External links
1944:
1941:
1940:
1922:
1915:
1889:
1861:
1793:
1769:
1740:
1734:978-3527306732
1733:
1696:
1674:
1665:
1659:978-1498754286
1658:
1634:
1599:
1598:
1596:
1593:
1592:
1591:
1584:
1581:
1524:
1521:
1520:
1519:
1514:
1510:
1506:
1502:
1498:
1439:
1436:
1376:August Hofmann
1341:Prins reaction
1293:
1290:
1263:
1262:
1257:
1253:
1249:
1245:
1241:
1237:
1233:
1229:
1225:
1221:
1217:
1201:potassium alum
1193:
1192:
1187:
1183:
1179:
1175:
1167:allyl chloride
1151:
1148:
1118:
1114:
1102:prop-2-en-1-ol
1089:
1086:
1085:
1080:
1058:
1057:
1053:standard state
1050:
1047:
1046:
1041:
1034:
1033:
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1021:
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772:P305+P351+P338
764:P303+P361+P353
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531:
529:Vapor pressure
525:
524:
521:
516:
513:
512:
509:
503:
502:
501:−129 °C
499:
493:
492:
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114:
112:
105:
102:
101:
99:
98:
90:
88:
83:
80:
79:
75:
74:
68:Vinyl carbinol
61:
57:
56:
53:Prop-2-en-1-ol
52:
51:
45:
44:
40:
39:
31:
30:
20:Allyl alcohol
15:
9:
6:
4:
3:
2:
2034:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2004:
2002:
1993:
1990:
1988:
1985:
1979:
1975:
1971:
1968:
1964:
1960:
1955:
1953:
1950:
1949:
1936:
1932:
1926:
1918:
1912:
1908:
1904:
1900:
1893:
1879:
1872:
1865:
1857:
1853:
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1701:
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1570:
1567:
1563:
1559:
1555:
1551:
1548:
1544:
1540:
1539:
1534:
1530:
1505:OH + HBr → CH
1495:
1494:
1493:
1491:
1490:allyl bromide
1486:
1484:
1480:
1476:
1471:
1469:
1465:
1464:polymerizable
1461:
1457:
1453:
1449:
1446:, which is a
1445:
1435:
1433:
1429:
1425:
1421:
1417:
1413:
1409:
1405:
1404:decomposition
1401:
1397:
1393:
1389:
1385:
1381:
1377:
1373:
1368:
1366:
1362:
1358:
1354:
1350:
1346:
1342:
1338:
1334:
1330:
1326:
1321:
1320:to allylol.
1319:
1315:
1314:decarboxylate
1311:
1307:
1303:
1299:
1289:
1287:
1283:
1278:
1276:
1275:hydrogenation
1273:, which upon
1272:
1268:
1214:
1213:
1212:
1210:
1209:allyl acetate
1206:
1202:
1198:
1172:
1171:
1170:
1168:
1164:
1161:
1157:
1147:
1145:
1142:
1138:
1134:
1130:
1126:
1123:. Like many
1111:
1107:
1103:
1099:
1095:
1094:Allyl alcohol
1083:
1076:
1071:
1054:
1048:
1045:
1044:External MSDS
1042:
1039:
1036:
1035:
1031:
1027:
1023:
1022:
1018:
1015:(Recommended)
1014:
1010:
1009:
1005:
1002:(Permissible)
1001:
997:
996:
992:
991:
986:
968:
964:
955:
954:
950:
946:
937:
936:
932:
928:
924:
922:
919:
918:
914:
911:
905:
904:
900:
898:
895:
894:
887:
880:
873:
849:
846:
845:
841:
840:
706:
703:
699:
698:
660:
657:
653:
652:
649:
646:
643:
639:
638:
634:
629:
624:
619:
615:
612:
608:
607:
603:
601:
596:
592:
587:
586:
582:
581:
576:
571:
567:
563:
559:
558:
550:
544:
540:
537:
536:
532:
530:
527:
526:
522:
519:
515:
514:
510:
508:
507:Boiling point
505:
504:
500:
498:
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66:1-Propen-3-ol
64:2-Propen-1-ol
62:Allyl alcohol
58:
50:
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41:
37:
32:
28:
23:
2017:Hepatotoxins
1977:
1934:
1925:
1898:
1892:
1881:. Retrieved
1877:
1864:
1819:
1816:Microbiology
1815:
1809:
1788:
1779:
1772:
1755:
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1714:
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1668:
1644:
1637:
1569:mitochondria
1562:microtubules
1536:
1526:
1487:
1472:
1441:
1438:Applications
1398:reaction of
1384:allyl iodide
1369:
1322:
1306:formic acids
1300:reacts with
1295:
1279:
1264:
1194:
1163:corporations
1153:
1137:plasticizers
1101:
1093:
1092:
989:
930:
908:Autoignition
843:
647:
599:
589:Main hazards
578:
542:
290:RTECS number
177:ChEMBL234926
78:Identifiers
60:Other names
1982:(in French)
1577:lachrymator
1573:glutathione
1543:metabolized
1529:hepatotoxic
1388:trituration
1133:drying oils
945:median dose
931:Lethal dose
910:temperature
897:Flash point
642:Signal word
583:(OHS/OSH):
491:0.854 g/ml
468:Appearance
424:Properties
215:100.003.156
157:CHEBI:16605
72:Weed drench
2001:Categories
1883:2024-01-24
1595:References
1566:hepatocyte
1380:hydrolysis
1363:, and the
1150:Production
1098:IUPAC name
925:2.5–18.0%
611:Pictograms
456:Molar mass
315:3W678R12M0
188:ChemSpider
106:3D model (
85:CAS Number
1972:(2004). "
1838:1465-2080
1650:CRC Press
1483:fungicide
1468:phthalate
1424:precursor
1318:dehydrate
1267:propylene
1205:propylene
1190:OH + NaCl
1129:precursor
1108:with the
828:P403+P235
824:P403+P233
816:P370+P378
800:P337+P313
796:P332+P313
768:P304+P340
760:P302+P352
756:P301+P310
602:labelling
523:Miscible
326:UN number
297:BA5075000
236:203-470-7
228:EC Number
1965:(NIOSH).
1856:16207909
1693:(NIOSH).
1631:(NIOSH).
1583:See also
1554:acrolein
1452:glycerol
1444:glycidol
1418:between
1416:reaction
1402:and its
1310:dioxalin
1298:glycerol
1286:propanol
1271:acrolein
1240:H → CH
1144:alcohols
1125:alcohols
1104:) is an
844:NFPA 704
573:Hazards
564:(χ)
533:17 mmHg
197:13872989
95:107-18-6
1959:"#0017"
1937:. 1984.
1847:2711876
1625:"#0017"
1564:of rat
1560:to the
1538:in vivo
1428:allicin
1400:allicin
1141:allylic
1075:what is
1073: (
1032:20 ppm
551:15.5 (H
539:Acidity
487:Density
266:PubChem
1913:
1854:
1844:
1836:
1758:: 15.
1731:
1656:
1558:damage
1523:Safety
1513:Br + H
1460:amines
1458:, and
1456:esters
1430:, and
1422:, the
1420:alliin
1353:enones
1343:, the
1302:oxalic
1135:, and
1070:verify
1067:
1040:(SDS)
1006:2 ppm
648:Danger
461:58.080
408:SMILES
254:C02001
168:ChEMBL
137:B00381
129:3DMet
43:Names
1874:(PDF)
1547:liver
1531:. In
1509:=CHCH
1501:=CHCH
1432:water
1329:allyl
1244:=CHCH
1220:=CHCH
1186:=CHCH
1178:=CHCH
1160:Shell
1117:=CHCH
990:NIOSH
415:C=CCO
373:InChI
330:1098
148:ChEBI
108:JSmol
1911:ISBN
1852:PMID
1834:ISSN
1729:ISBN
1654:ISBN
1533:rats
1479:weed
1410:and
1374:and
1316:and
1232:+ CH
1224:+ 1/
1158:and
1156:Olin
1026:IDLH
836:P501
832:P405
820:P391
812:P363
808:P362
804:P361
792:P330
788:P322
784:P321
780:P312
776:P311
752:P280
748:P273
744:P271
740:P270
736:P264
732:P261
728:P243
724:P242
720:P241
716:P240
712:P233
708:P210
694:H400
690:H335
686:H331
682:H319
678:H315
674:H311
670:H302
666:H301
662:H225
477:Odor
306:UNII
279:7858
245:KEGG
1903:doi
1842:PMC
1824:doi
1820:151
1760:doi
1721:doi
1552:to
1545:by
1492::
1434:).
1426:of
1390:of
1382:of
1378:by
1335:or
1327:of
1304:or
1288:.
1284:of
1256:+ H
1252:CCH
1207:to
1013:REL
1000:PEL
600:GHS
555:O)
342:EPA
269:CID
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1961:.
1933:.
1909:.
1876:.
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818:,
814:,
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794:,
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546:a
543:K
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446:6
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440:3
437:C
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340:(
110:)
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