26:
35:
276:
169:
450:
455:
440:
445:
668:
1018:
for the analysis of various carboxylic compounds which are ubiquitous in nature. The fact that the reaction is rapid and occurs readily makes it attractive. However, it can form artifacts which complicate spectral interpretation. Such artifacts are usually the trimethylsilylmethyl esters,
1047:
Trimethylsilyldiazomethane is highly toxic. It has been implicated in the death of at least two chemists, a pharmaceutical worker in
Windsor, Nova Scotia and one in New Jersey. Inhalation of diazomethane is known to cause
463:
420:
1265:
Kühnel, E.; Laffan, D. D. P.; Lloyd-Jones, G. C.; Martínez del Campo, T.; Shepperson, I. R.; Slaughter, J. L. (2007). "Mechanism of Methyl
Esterification of Carboxylic Acids by Trimethylsilyldiazomethane".
908:
1302:
Armin
Presser & Antje Hüfner (2004). "Diazo(trimethylsilyl)methane – A Mild and Efficient Reagent for the Methylation of Carboxylic Acids and Alcohols in Natural Products".
681:
577:
1384:
775:
Trimethylsilyldiazomethane is useful for conversion of carboxylic acids to their methyl esters in high yield. The typical reaction conditions for this purpose use
787:
as the active methylating agent, by an acid-catalyzed reaction between trimethylsilyldiazomethane and the alcohol with trimethylsilyldiazomethane as byproduct:
325:
581:
756:
1483:
1106:
Seyferth, Dietmar; Menzel, Horst; Dow, Alan W.; Flood, Thomas C. (1972). "Trimethylsilyl-substituted diazoalkanes I. Trimethylsilyldiazomethane".
1436:
Murphy, N. G.; Varney, S. M.; Tallon, J. M.; Thompson, J. R.; Blanc, P. D. (2009). "Fatal
Occupational Exposure to Trimethylsilyl-Diazomethane".
513:
1015:
1354:
1498:
290:
1078:
Seyferth, Dietmar.; Dow, Alan W.; Menzel, Horst.; Flood, Thomas C. (1968). "Trimethylsilyldiazomethane and trimethylsilylcarbene".
114:
913:
When the methanol is omitted, substantial amounts of trimethylsilyl ester and trimethylmethyl ester products are formed as well.
107:
793:
1169:
1055:
It is possible that upon contact with water on the surface of the lung, trimethylsilyldiazomethane converts to diazomethane.
1035:
is present. Acid-catalysed methanolysis is necessary to achieve near-quantitative yields of the desired methyl esters, RCO
561:
25:
1370:
688:
509:
200:
499:
233:
454:
449:
1493:
254:
625:
920:
176:
1478:
760:
525:
194:
1134:
1408:
1245:
609:
439:
589:
164:
704:
585:
1337:
Moody, Christopher J.; Shioiri, Takayuki; Aoyama, Toyohiko (2011). "Diazo(trimethylsilyl)methyllithium".
533:
1488:
477:
444:
432:
47:
34:
744:
605:
593:
1438:
1108:
549:
271:
73:
521:
1454:
1319:
764:
629:
541:
126:
601:
537:
553:
1350:
1284:
1268:
1190:
1165:
1080:
732:
728:
644:
565:
1446:
1342:
1311:
1276:
1240:
1230:
1199:
1157:
1152:
Shioiri, Takayuki; Aoyama, Toyohiko; Snowden, Timothy (2001). "Trimethylsilyldiazomethane".
1116:
1088:
962:
The lithio compound is versatile. From it can be prepared other trimethylsilyldiazoalkanes:
617:
353:
146:
242:
83:
1049:
736:
573:
597:
275:
168:
1188:
Takayuki
Shioiri; Toyohiko Aoyama; Shigehiro Mori (1990). "Trimethylsilyldiazomethane".
720:
659:
505:
1120:
1006:
reacts with ketones and aldehydes to give, depending on the substituents, acetylenes.
1472:
1458:
1385:"N.S. probe into pharma worker's death finds vent hoods turned off in lab | SaltWire"
405:
157:
1323:
637:
927:
740:
545:
222:
1346:
1161:
916:
It also reacts with alcohols to give methyl ethers, whereas diazomethane may not.
650:
557:
613:
1450:
1315:
517:
384:
137:
1235:
1218:
1203:
569:
529:
1288:
1280:
1219:"Trimethylsilyldiazo[13C]methane: A Versatile C-Labelling Reagent"
1032:
776:
1092:
784:
780:
724:
491:
209:
177:
1409:"OSHA accident report regarding a trimethylsilyldiazomethane fatality"
838:
658:
Except where otherwise noted, data are given for materials in their
723:. Trimethylsilyldiazomethane, which is a commercially available,
113:
106:
96:
621:
633:
487:
483:
1052:; trimethylsilyldiazomethane is suspected to behave similarly.
259:
903:{\displaystyle {\ce {CH3OH\ +TMSCHN2->CH3OTMS\ +CH2N2}}}
783:. Under these conditions, diazomethane itself is generated
767:
variant, with C at the diazomethyl carbon, is also known.
896:
883:
861:
830:
808:
755:
Trimethylsilyldiazomethane can be prepared by treating
676:
1339:
E-EROS Encyclopedia of
Reagents for Organic Synthesis
1154:
e-EROS Encyclopedia of
Reagents for Organic Synthesis
796:
902:
1246:20.500.11820/c801073c-6b4b-4a85-be68-2c4313b6e53d
1014:It has also been employed widely in tandem with
221:
1217:Nottingham, Chris; Lloyd-Jones, Guy C. (2018).
82:
1073:
1071:
926:Trimethylsilyldiazomethane is deprotonated by
1260:
1258:
1256:
8:
1058:Trimethylsilyldiazomethane is nonexplosive.
410:96.0 °C (204.8 °F; 369.1 K)
299:InChI=1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
309:InChI=1/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
274:
167:
145:
17:
1431:
1429:
1244:
1234:
895:
890:
882:
877:
860:
855:
842:
840:
833:
829:
824:
807:
802:
797:
795:
241:
757:(trimethylsilyl)methylmagnesium chloride
1067:
330:
295:
270:
199:
923:with allyl sulfides and allyl amines.
739:. Its behavior is akin to the reagent
158:
302:Key: ONDSBJMLAHVLMI-UHFFFAOYSA-N
7:
1371:"Guilty plea in N.S. drug lab death"
1183:
1181:
312:Key: ONDSBJMLAHVLMI-UHFFFAOYAN
212:
839:
14:
919:The compound is a reagent in the
666:
453:
448:
443:
438:
371:
365:
33:
24:
662:(at 25 °C , 100 kPa).
377:
1484:Reagents for organic chemistry
747:(TMS) analog is nonexplosive.
359:
1:
1347:10.1002/047084289X.rd019.pub2
1162:10.1002/047084289X.rt298.pub2
1121:10.1016/S0022-328X(00)82916-2
1135:"Trimethylsilyldiazomethane"
61:Diazo(trimethylsilyl)methane
51:(Diazomethyl)trimethylsilane
1031:, formed when insufficient
19:Trimethylsilyldiazomethane
1515:
701:Trimethylsilyldiazomethane
201:Trimethylsilyldiazomethane
59:Trimethylsilyldiazomethane
1451:10.1080/15563650903076924
1316:10.1007/s00706-004-0188-4
719:. It is classified as a
656:
419:
414:
346:
321:
286:
66:
56:
46:
41:
32:
23:
1499:Trimethylsilyl compounds
1236:10.15227/orgsyn.095.0374
1204:10.15227/orgsyn.068.0001
1139:pubchem.ncbi.nlm.nih.gov
761:diphenyl phosphorazidate
500:Precautionary statements
400:greenish-yellow liquid
1281:10.1002/anie.200702131
904:
705:organosilicon compound
1269:Angew. Chem. Int. Ed.
921:Doyle–Kirmse reaction
905:
765:isotopically labelled
794:
707:with the formula (CH
1109:J. Organomet. Chem.
1093:10.1021/ja01006a055
898:
885:
863:
848:
832:
810:
392: g·mol
127:Beilstein Reference
20:
1494:Methylating agents
900:
886:
873:
851:
820:
798:
689:Infobox references
18:
1275:(37): 7075–7078.
1223:Organic Syntheses
1191:Organic Syntheses
1081:J. Am. Chem. Soc.
946:+ BuLi → (CH
889:
876:
869:
866:
854:
849:
847:
845:
823:
816:
813:
801:
733:methylating agent
729:organic chemistry
697:Chemical compound
695:
694:
645:Safety data sheet
478:Hazard statements
255:CompTox Dashboard
115:Interactive image
108:Interactive image
1506:
1463:
1462:
1433:
1424:
1423:
1421:
1419:
1405:
1399:
1398:
1396:
1395:
1389:www.saltwire.com
1381:
1375:
1374:
1367:
1361:
1360:
1341:. pp. 1–7.
1334:
1328:
1327:
1304:Chemical Monthly
1299:
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1185:
1176:
1175:
1149:
1143:
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1131:
1125:
1124:
1103:
1097:
1096:
1087:(4): 1080–1082.
1075:
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899:
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834:
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828:
821:
814:
811:
809:
806:
799:
737:carboxylic acids
679:
673:
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511:
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493:
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391:
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373:
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361:
354:Chemical formula
279:
278:
263:
261:
245:
225:
214:
203:
179:
171:
160:
149:
117:
110:
86:
37:
28:
21:
1514:
1513:
1509:
1508:
1507:
1505:
1504:
1503:
1479:Diazo compounds
1469:
1468:
1467:
1466:
1435:
1434:
1427:
1417:
1415:
1407:
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1402:
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1300:
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1254:
1216:
1215:
1211:
1187:
1186:
1179:
1172:
1151:
1150:
1146:
1133:
1132:
1128:
1105:
1104:
1100:
1077:
1076:
1069:
1064:
1050:pulmonary edema
1045:
1038:
1030:
1026:
1022:
1012:
1005:
1001:
997:
989:
985:
981:
978:+ RX → (CH
977:
973:
969:
957:
953:
949:
945:
941:
937:
792:
791:
773:
753:
718:
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685:
684: ?)
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100:
89:
76:
62:
60:
52:
12:
11:
5:
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1510:
1502:
1501:
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1491:
1486:
1481:
1471:
1470:
1465:
1464:
1439:Clin. Toxicol.
1425:
1400:
1376:
1362:
1356:978-0471936237
1355:
1329:
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1252:
1209:
1177:
1170:
1144:
1126:
1115:(2): 279–290.
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1044:
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837:
827:
819:
805:
772:
769:
752:
749:
745:trimethylsilyl
721:diazo compound
716:
712:
708:
696:
693:
692:
687:
665:
664:
660:standard state
657:
654:
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648:
641:
640:
578:P303+P361+P353
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1042:
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1034:
1017:
1009:
1007:
965:
964:
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933:
932:
931:
929:
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922:
917:
914:
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835:
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803:
790:
789:
788:
786:
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778:
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768:
766:
762:
758:
750:
748:
746:
742:
738:
734:
730:
726:
722:
706:
702:
690:
683:
678:
661:
655:
652:
651:External MSDS
649:
646:
643:
642:
504:
501:
497:
496:
482:
479:
475:
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465:
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423:
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409:
407:
406:Boiling point
404:
403:
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358:
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351:
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272:DTXSID8074653
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163:
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159:ECHA InfoCard
156:
155:
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128:
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55:
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45:
40:
36:
31:
27:
22:
16:
1489:Carbosilanes
1442:
1437:
1416:. Retrieved
1412:
1403:
1392:. Retrieved
1388:
1379:
1365:
1338:
1332:
1307:
1303:
1297:
1272:
1267:
1226:
1222:
1212:
1195:
1189:
1153:
1147:
1138:
1129:
1112:
1107:
1101:
1084:
1079:
1057:
1054:
1046:
1013:
1010:Applications
993:
961:
928:butyllithium
925:
918:
915:
912:
774:
754:
741:diazomethane
700:
699:
469:
421:
67:Identifiers
57:Other names
15:
1229:: 374–402.
751:Preparation
464:Signal word
397:Appearance
347:Properties
165:100.131.243
1473:Categories
1445:(7): 712.
1394:2022-05-03
1171:0471936235
1062:References
743:, but the
433:Pictograms
385:Molar mass
338:==C(C)(C)C
243:QI98HQO8C4
138:ChemSpider
95:3D model (
84:18107-18-1
74:CAS Number
48:IUPAC name
1459:218859698
1413:osha.gov/
771:Reactions
630:P403+P235
626:P403+P233
618:P370+P378
610:P332+P313
590:P308+P313
586:P307+P311
582:P304+P340
574:P302+P352
424:labelling
333:C(C)(C)#N
186:605-915-4
178:EC Number
1418:10 April
1324:93420685
1289:17691089
1033:methanol
836:→
777:methanol
727:used in
415:Hazards
132:1902903
785:in situ
781:solvent
779:as a co
725:reagent
703:is the
682:what is
680: (
390:114.223
210:PubChem
1457:
1353:
1322:
1287:
1168:
1043:Safety
1002:SiCLiN
990:+ LiX
974:SiCLiN
958:+ BuH
954:SiCLiN
868:
822:TMSCHN
815:
677:verify
674:
647:(SDS)
470:Danger
326:SMILES
223:167693
147:146699
42:Names
1455:S2CID
1320:S2CID
1310:(8).
1198:: 1.
1016:GC-MS
986:SiCRN
942:SiCHN
763:. An
759:with
731:as a
715:SiCHN
291:InChI
97:JSmol
1420:2020
1351:ISBN
1285:PMID
1166:ISBN
1039:Me.
1027:SiMe
865:OTMS
844:acid
638:P501
634:P405
622:P391
614:P362
606:P320
602:P314
598:P311
594:P310
570:P284
566:P281
562:P280
558:P273
554:P271
550:P270
546:P264
542:P261
538:P260
534:P243
530:P242
526:P241
522:P240
518:P233
514:P210
510:P202
506:P201
492:H370
488:H350
484:H330
234:UNII
195:MeSH
1447:doi
1343:doi
1312:doi
1308:135
1277:doi
1241:hdl
1231:doi
1200:doi
1158:doi
1117:doi
1089:doi
1019:RCO
994:(CH
966:(CH
934:(CH
735:of
422:GHS
260:EPA
213:CID
1475::
1453:.
1443:47
1428:^
1411:.
1387:.
1349:.
1318:.
1306:.
1283:.
1273:46
1255:^
1239:.
1227:95
1225:.
1221:.
1196:68
1194:.
1180:^
1164:.
1156:.
1137:.
1113:44
1085:90
1070:^
1023:CH
930::
875:CH
853:CH
812:OH
800:CH
636:,
632:,
628:,
624:,
620:,
616:,
612:,
608:,
604:,
600:,
596:,
592:,
588:,
584:,
580:,
576:,
572:,
568:,
564:,
560:,
556:,
552:,
548:,
544:,
540:,
536:,
532:,
528:,
524:,
520:,
516:,
512:,
508:,
490:,
486:,
426::
378:Si
369:10
1461:.
1449::
1422:.
1397:.
1373:.
1359:.
1345::
1326:.
1314::
1291:.
1279::
1249:.
1243::
1233::
1207:.
1202::
1174:.
1160::
1141:.
1123:.
1119::
1095:.
1091::
1037:2
1029:3
1025:2
1021:2
1004:2
1000:3
998:)
996:3
988:2
984:3
982:)
980:3
976:2
972:3
970:)
968:3
956:2
952:3
950:)
948:3
944:2
940:3
938:)
936:3
892:2
888:N
879:2
871:+
857:3
826:2
818:+
804:3
717:2
713:3
711:)
709:3
672:Y
375:2
372:N
366:H
363:4
360:C
262:)
258:(
99:)
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