792:
291:
216:
791:
35:
580:
570:
575:
787:
889:
1229:, (organo-magnesium compounds), which are easier to handle and less flammable, replaced organo-zinc compounds in most laboratory syntheses. Due to differences in reactivity (as well as in reaction byproducts) between organo-zinc compounds and Grignard reagents, organo-zinc compounds may be preferred in some syntheses.
1074:, eventually causing blindness. If dimethylzinc contacts the skin, it causes thermal and acid burns by reacting with moisture on skin. Unless washed quickly, skin may be scarred. Ingestion, while unlikely, also causes immediate burns. Nausea, vomiting, cramps, and diarrhea may follow, and tissues may
1472:
A. Haaland; J. C. Green; G. S. McGrady; A. J. Downs; E. Gullo; M. J. Lyall; J. Timberlake; A. V. Tutukin; H. V. Volden; K.-A. Østby (2003). "The length, strength and polarity of metal–carbon bonds: dialkylzinc compounds studied by density functional theory calculations, gas electron diffraction and
793:
790:
815:
808:
588:
550:
1070:
and death. Eyes are immediately and severely irritated and burned by liquid, vapor, or dilute solutions. If not removed by thorough flushing with water, this chemical may permanently damage the
902:
702:
340:
706:
1606:
1225:. It was used for a long time to introduce methyl groups into organic molecules or to synthesize organometallic compounds containing methyl groups.
1427:
1205:
in an airtight vessel, a flame burst out when the seal was broken. In the laboratory, this synthesis method remains unchanged today, except that
638:
1543:
1129:
Dimethylzinc fire must be extinguished with dry sand. The fire reacts violently or explosively with water, generating very flammable
1287:
1244:
305:
34:
2140:
1118:
in air. It burns in air with a blue flame, giving off a garlic-like odor. The products of decomposition (fire smoke) include
1055:
616:
531:
2150:
2135:
690:
909:
822:
1599:
632:
248:
579:
2130:
1421:
John Bacsa; Felix Hanke; Sarah
Hindley; Rajesh Odedra; George R. Darling; Anthony C. Jones; Alexander Steiner (2011).
269:
650:
801:
1299:
1066:
Inhalation of dimethylzinc mist or vapor causes immediate irritation of the upper respiratory tract, and may cause
734:
2145:
1264:
1051:
1349:
1561:
837:
666:
569:
1592:
694:
574:
211:
1094:
1020:
1146:
674:
2065:
1636:
1198:
1177:
is ordered. The molecules are linear with Zn-C bond lengths measuring 192.7(6) pm. The structure of the
726:
602:
562:
62:
1078:
if not promptly treated. Upon heating, dimethylzinc vapor decomposes to irritating and toxic products.
754:
738:
1675:
1559:
Mohammad Afzaal; Mohammad A. Malik; Paul O’Brien (2007). "Preparation of zinc containing materials".
1337:
925:
481:
624:
1475:
286:
119:
1173:
high-temperature phase shows a two-dimensional disorder, while the low-temperature phase which is
662:
1859:
1218:
545:
Spontaneously ignites in air and violently reacts with water, evolving irritant and toxic fumes.
1157:. Improperly handled containers of dimethylzinc can explode, causing serious injuries or death.
678:
2013:
1539:
1454:
1345:
1226:
1222:
952:
193:
153:
1923:
1804:
1570:
1516:
1503:"Notiz über eine neue Reihe organischer Körper, welche Metalle, Phosphor u. s. w. enthalten"
1498:
1480:
1444:
1436:
1190:
1123:
929:
746:
612:
363:
722:
257:
1997:
1875:
1507:
868:
863:
1390:
129:
742:
290:
215:
173:
1931:
1911:
1854:
1828:
1771:
1703:
1615:
1449:
1422:
1233:
1031:
880:
620:
471:
2124:
1887:
1849:
1796:
1747:
1739:
1727:
1719:
1202:
1194:
1111:
968:
714:
507:
452:
432:
422:
204:
766:
730:
2081:
2045:
2029:
1985:
1899:
1841:
1836:
1779:
1755:
1711:
1695:
1407:
1043:
682:
456:
608:
237:
758:
686:
1969:
1763:
1326:
1008:
956:
646:
1791:
1683:
1174:
1170:
1134:
1133:
gas which can explode in air upon catching fire, and lung-irritating smoke of
1119:
1115:
654:
642:
442:
384:
184:
1520:
1341:
1178:
1086:
1067:
1047:
670:
491:
1458:
1440:
718:
17:
1330:
1241:
1138:
1082:
940:
821:
814:
807:
800:
773:
41:
1122:, which itself is not toxic, but its fumes can irritate lungs and cause
1232:
Its high vapor pressure has led to extensive uses in the production of
1142:
1130:
1035:
460:
412:
224:
1574:
1484:
1283:
1206:
1150:
1071:
1039:
1023:
976:
937:
448:
45:
1502:
879:
Except where otherwise noted, data are given for materials in their
1237:
1166:
1154:
1075:
979:
464:
164:
152:
142:
1584:
750:
1318:
1260:
1256:
1046:
of dimethylzinc is 230.13 K (−43.02 °C) ± 0.02 K. The
1027:
1007:
Sodium assists the reaction of the zinc with the methyl iodide.
972:
933:
762:
402:
49:
1588:
1322:
1295:
1291:
1252:
1248:
1090:
1423:"The Solid State Structures of Dimethylzinc and Diethylzinc"
274:
710:
698:
658:
1137:. Dimethylzinc fire reacts violently or explosively with
785:
897:
1026:, which has a characteristic disagreeable garlic-like
924:, also known as zinc methyl, DMZ, or DMZn, is a toxic
520:
129.20 J/(mol∙K) (liquid at 25 °C (77 °F))
1951:
1668:
1629:
1622:
1209:or copper compounds are used to activate the zinc.
1181:shows a very similar Zn-C distance of 193.0(2) pm.
1217:Dimethylzinc has been of great importance in the
236:
1236:, e.g. metalorganic chemical vapor deposition (
789:
128:
1169:the compound exists in two modifications. The
1600:
324:InChI=1/2CH3.Zn/h2*1H3;/rC2H6Zn/c1-3-2/h1-2H3
8:
951:. It belongs to the large series of similar
486:0.1627 W/(m∙K) at 70 °C (158 °F)
1948:
1626:
1607:
1593:
1585:
1385:
289:
214:
192:
26:
1448:
1383:
1381:
1379:
1377:
1375:
1373:
1371:
1369:
1367:
1365:
256:
1536:Organozinc reagents in organic synthesis
1508:Liebigs Annalen der Chemie und Pharmacie
1402:
1400:
1308:
1302:
1273:
1267:
1103:
1099:
1000:
996:
992:
988:
947:
943:
375:
371:
1428:Angewandte Chemie International Edition
1361:
496:0.807 mPa·s at 70 °F (21 °C)
345:
310:
285:
1201:. After heating a mixture of zinc and
427:−42 °C (−44 °F; 231 K)
205:
437:46 °C (115 °F; 319 K)
317:Key: AXAZMDOAUQTMOW-UHFFFAOYSA-N
172:
7:
1189:Dimethylzinc was first prepared by
1030:. It is a very reactive and strong
1019:Dimethylzinc is a colorless mobile
327:Key: AXAZMDOAUQTMOW-WPFVDKAYAX
227:
25:
1336:It is used as an accelerator in
1038:and often sold as a solution in
887:
578:
573:
568:
33:
883:(at 25 °C , 100 kPa).
1240:) for the preparation of wide
967:It is formed by the action of
532:Occupational safety and health
1:
1473:photoelectron spectroscopy".
1408:"Dimethylzinc (CAS 544-97-8)"
1081:Contact of dimethylzinc with
1050:molecule of dimethylzinc is
1247:semiconducting films (e.g.
1126:, severe injury, or death.
1089:. Dimethylzinc oxidises in
982:at elevated temperatures.
2167:
1350:methyltitanium trichloride
1011:is formed as a byproduct.
389:95.478 g/mol
1538:. Boca Raton: CRC Press.
877:
849:
549:
529:
524:
500:
356:
336:
301:
112:
104:Zinc trihydrogenmethanide
71:
61:
56:
32:
1952:Organozinc(II) compounds
1562:New Journal of Chemistry
1521:10.1002/jlac.18490710206
845:0 °F (−18 °C)
633:Precautionary statements
314:InChI=1S/2CH3.Zn/h2*1H3;
2141:Foul-smelling chemicals
1630:Organozinc(I) compounds
1093:very slowly, producing
459:; decomposes in water,
1441:10.1002/anie.201105099
1114:and can spontaneously
796:
417:1.386 g/cm at 10.5 °C
1534:Erdik, Ender (1996).
1290:semiconductors (e.g.
1199:University of Marburg
1193:during his work with
1110:Dimethylzinc is very
795:
2151:Pyrophoric materials
2136:Organozinc compounds
1338:rubber vulcanization
1095:methylzinc methoxide
1062:Toxicity and hazards
778:(fire diamond)
482:Thermal conductivity
1476:Dalton Transactions
1435:(49): 11685–11687.
1325:), which have many
1147:2,2-dichloropropane
1085:may form explosive
1034:. It is soluble in
926:organozinc compound
29:
2131:Methylating agents
910:Infobox references
850:Related compounds
797:
27:
2118:
2117:
2077:
2076:
1664:
1663:
1569:(12): 2029–2040.
1545:978-0-8493-9151-4
1479:(22): 4356–4366.
1346:methylating agent
1227:Grignard reagents
1223:organic compounds
1149:. It explodes in
1054:at Zn center and
918:Chemical compound
916:
915:
856:Related compounds
603:Hazard statements
397:Colorless liquid
270:CompTox Dashboard
154:Interactive image
16:(Redirected from
2158:
2146:Methyl complexes
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1575:10.1039/b712235g
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1485:10.1039/B306840B
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1418:
1412:
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1395:
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1191:Edward Frankland
1124:metal fume fever
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930:chemical formula
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501:Thermochemistry
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364:Chemical formula
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1306:
1300:
1286:precursors for
1278:
1271:
1265:
1215:
1197:in 1849 at the
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1163:
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932:
919:
912:
907:
906:
905: ?)
896:
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888:
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873:
869:Dimethylmercury
864:Dimethylcadmium
857:
842:
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243:
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159:
146:
135:
122:
108:
107:
83:Dimethylzincane
67:
52:
38:
23:
22:
15:
12:
11:
5:
2164:
2162:
2154:
2153:
2148:
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1616:Zinc compounds
1614:
1612:
1611:
1604:
1597:
1589:
1581:
1580:
1551:
1544:
1526:
1515:(2): 213–216.
1490:
1464:
1413:
1396:
1391:"Dimethylzinc"
1360:
1359:
1357:
1354:
1333:applications.
1234:semiconductors
1214:
1211:
1186:
1183:
1162:
1159:
1063:
1060:
1058:at C centers.
1032:reducing agent
1016:
1013:
1005:
1004:
964:
961:
917:
914:
913:
908:
886:
885:
881:standard state
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703:P303+P361+P353
695:P301+P330+P331
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472:Vapor pressure
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98:Zinc methanide
96:
95:Zinc carbanide
93:
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84:
81:
78:
77:2-Zincapropane
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1243:
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1230:
1228:
1224:
1220:
1212:
1210:
1208:
1204:
1203:methyl iodide
1200:
1196:
1195:Robert Bunsen
1192:
1184:
1182:
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1079:
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1037:
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1025:
1022:
1014:
1012:
1010:
985:
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981:
978:
974:
970:
969:methyl iodide
962:
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954:
942:
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935:
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927:
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904:
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508:Heat capacity
505:
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453:diethyl ether
450:
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423:Melting point
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206:ECHA InfoCard
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80:Dimethyl zinc
79:
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64:
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55:
51:
47:
43:
36:
31:
28:Dimethylzinc
19:
1957:
1566:
1560:
1554:
1535:
1529:
1512:
1506:
1499:E. Frankland
1493:
1474:
1467:
1432:
1426:
1416:
1335:
1310:
1303:
1275:
1268:
1231:
1216:
1188:
1164:
1128:
1109:
1080:
1065:
1044:triple point
1018:
1006:
966:
922:Dimethylzinc
921:
920:
838:Autoignition
774:
594:
551:
541:Main hazards
530:
512:
457:hydrocarbons
113:Identifiers
72:Other names
66:Dimethylzinc
1344:, and as a
1282:) and as p-
1167:solid state
1009:Zinc iodide
987:2 Zn + 2 CH
963:Preparation
957:diethylzinc
840:temperature
589:Signal word
535:(OHS/OSH):
447:Soluble in
394:Appearance
357:Properties
212:100.008.077
174:CHEBI:51497
101:Zinc methyl
18:Zinc methyl
2125:Categories
1356:References
1327:electronic
1175:monoclinic
1171:tetragonal
1135:zinc oxide
1120:zinc oxide
1112:pyrophoric
1056:tetragonal
1015:Properties
563:Pictograms
476:50.13 kPa
443:Solubility
385:Molar mass
258:8H6R0N8W2F
185:ChemSpider
141:3D model (
120:CAS Number
92:Methylzinc
63:IUPAC name
1342:fungicide
1219:synthesis
1179:gas-phase
1161:Structure
1087:peroxides
1068:pneumonia
1048:monomeric
991:I → Zn(CH
953:compounds
928:with the
755:P402+P404
747:P370+P378
707:P304+P340
651:P231+P232
554:labelling
492:Viscosity
44:, Black:
1998:Zn(CH(CH
1676:Zn(acac)
1669:Zinc(II)
1501:(1849).
1459:21919175
1331:photonic
1242:band gap
1139:methanol
1083:oxidants
1076:ulcerate
1021:volatile
975:or zinc-
955:such as
775:NFPA 704
525:Hazards
194:10254473
130:544-97-8
48:, Grey:
2014:Zn(C(CH
1623:Zinc(I)
1450:3326375
1340:, as a
1185:History
1165:In the
1143:ethanol
1131:methane
1040:hexanes
1036:alkanes
903:what is
901: (
461:ethanol
413:Density
407:Garlic
379:
225:PubChem
40:White:
1829:Zn(OH)
1806:Zn(ClO
1728:Zn(ClO
1712:Zn(CN)
1542:
1457:
1447:
1284:dopant
1207:copper
1151:oxygen
1116:ignite
1072:cornea
1052:linear
1042:. The
1024:liquid
977:sodium
898:verify
895:
595:Danger
449:xylene
341:SMILES
57:Names
2066:ZnICH
1986:Zn(CH
1958:Zn(CH
1780:Zn(NO
1772:ZnMoO
1740:ZnCrO
1288:III–V
1245:II–VI
1238:MOCVD
1155:ozone
1102:ZnOCH
999:+ ZnI
980:alloy
465:acids
370:Zn(CH
306:InChI
238:11010
165:ChEBI
143:JSmol
2046:Zn(C
2030:Zn(C
1990:COO)
1970:Zn(C
1855:ZnTe
1850:ZnSe
1842:ZnSO
1720:ZnCl
1704:ZnCO
1696:ZnBr
1684:Zn(N
1540:ISBN
1455:PMID
1329:and
1319:GaAs
1261:ZnTe
1257:ZnSe
1213:Uses
1153:and
1145:and
1028:odor
973:zinc
767:P501
763:P405
759:P403
751:P391
743:P363
739:P361
735:P338
731:P335
727:P334
723:P321
719:P317
715:P316
711:P305
699:P302
691:P280
687:P273
683:P264
679:P260
675:P243
671:P242
667:P241
663:P240
659:P235
655:P233
647:P223
643:P222
639:P210
625:H410
621:H314
617:H260
613:H250
609:H225
463:and
403:Odor
249:UNII
89:DMZn
2101:ZnO
1936:(PO
1924:ZnP
1837:ZnS
1797:ZnO
1792:ZnO
1764:ZnI
1756:ZnH
1748:ZnF
1645:(CH
1571:doi
1517:doi
1481:doi
1445:PMC
1437:doi
1348:in
1323:InP
1296:AlP
1292:AlN
1253:ZnS
1249:ZnO
1221:of
1091:air
971:on
552:GHS
275:EPA
228:CID
86:DMZ
2127::
2097:46
2088:24
1932:Zn
1912:Zn
1900:Zn
1892:As
1888:Zn
1880:Sb
1876:Zn
1860:Zn
1641:(C
1637:Zn
1567:31
1565:.
1513:71
1511:.
1505:.
1453:.
1443:.
1433:50
1431:.
1425:.
1399:^
1364:^
1352:.
1321:,
1317:,
1314:As
1309:1−
1307:Ga
1301:Al
1298:,
1294:,
1279:Te
1274:1−
1272:Hg
1266:Cd
1263:,
1259:,
1255:,
1251:,
1141:,
1107:.
1098:CH
959:.
934:Zn
765:,
761:,
757:,
753:,
749:,
745:,
741:,
737:,
733:,
729:,
725:,
721:,
717:,
713:,
709:,
705:,
701:,
697:,
693:,
689:,
685:,
681:,
677:,
673:,
669:,
665:,
661:,
657:,
653:,
649:,
645:,
641:,
623:,
619:,
615:,
611:,
556::
455:,
451:,
348:CC
50:Zn
2106:4
2092:H
2083:C
2070:I
2068:2
2060:2
2058:)
2056:3
2054:O
2052:5
2050:H
2048:3
2040:2
2038:)
2036:5
2034:H
2032:6
2024:2
2022:)
2020:3
2018:)
2016:3
2008:2
2006:)
2004:2
2002:)
2000:3
1992:2
1988:3
1980:2
1978:)
1976:5
1974:H
1972:2
1964:2
1962:)
1960:3
1942:2
1940:)
1938:4
1934:3
1926:2
1918:2
1916:P
1914:3
1906:2
1904:N
1902:3
1894:2
1890:3
1882:2
1878:3
1870:7
1868:O
1866:2
1864:P
1862:2
1844:4
1831:2
1820:2
1815:)
1811:4
1799:2
1786:2
1784:)
1782:3
1774:4
1766:2
1758:2
1750:2
1742:4
1734:2
1732:)
1730:3
1722:2
1714:2
1706:3
1698:2
1690:2
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1686:3
1678:2
1655:2
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1651:5
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1647:3
1643:5
1639:2
1608:e
1601:t
1594:v
1577:.
1573::
1548:.
1523:.
1519::
1487:.
1483::
1461:.
1439::
1410:.
1393:.
1311:x
1304:x
1276:x
1269:x
1104:3
1100:3
1001:2
997:2
995:)
993:3
989:3
948:2
946:)
944:3
941:H
938:C
936:(
893:N
824:W
816:3
809:4
802:3
515:)
513:C
511:(
376:2
374:)
372:3
277:)
273:(
145:)
46:C
42:H
20:)
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