33:
42:
266:
183:
24:
526:
521:
733:
1087:
Driess, Matthias; Pritzkow, Hans; Skipinski, Markus; Winkler, Uwe (1997). "Synthesis and Solid State
Structures of Sterically Congested Sodium and Cesium Silyl(fluorosilyl)phosphanide Aggregates and Structural Characterization of the Trimeric Sodium Bis(trimethylsilyl)amide".
534:
501:
791:
used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as
636:
1070:
Watson, B. T.; Lebel, H. "Sodium bis(trimethylsilyl)amide" in
Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
624:
746:
1221:
1179:
1137:
120:
741:
327:
632:
32:
1249:
694:
280:
688:
753:
1259:
1051:
482:
1200:
612:
628:
578:
178:
834:
Although the Na–N bond is polar covalent as a solid, when dissolved in nonpolar solvents this compound is
244:
608:
525:
41:
1254:
190:
823:
706:
261:
301:
InChI=1/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1/rC6H18NNaSi2/c1-9(2,3)7(8)10(4,5)6/h1-6H3
769:
930:
in a two step process that begins with N-alkylation followed by hydrolysis of the N–Si bonds:
911:
NaHMDS deprotonates compounds containing weakly acidic O–H, S–H, and N–H bonds. These include
520:
160:
1215:
1173:
1131:
548:
513:
54:
644:
616:
96:
8:
885:
265:
182:
86:
1161:"Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene"
835:
465:
140:
1207:
1165:
1123:
858:
715:
1201:
J. Christopher McWilliams, Fred J. Fleitz, Nan Zheng, and Joseph D. Armstrong, III.
222:
1099:
1075:
1071:
900:
819:
788:
640:
427:
350:
23:
1090:
787:. This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong
596:
1202:
1160:
1118:
904:
808:
724:
711:
588:
570:
584:
1243:
1119:"Preparation of (E)-1-Dimethylamino-3-tert-Butyldimethylsiloxy-1,3-Butadiene"
796:
600:
416:
406:
171:
1116:
1158:
923:
893:
889:
888:
of halocarbons. These carbene reagents add to alkenes to give substituted
912:
648:
652:
620:
438:
375:
191:
151:
1103:
660:
562:
233:
723:
Except where otherwise noted, data are given for materials in their
1011:
This method has been extended to aminomethylation via the reagent
668:
119:
1001:
881:
874:
804:
800:
592:
452:
448:
396:
209:
866:
604:
1086:
1005:
927:
916:
870:
815:
109:
249:
411:
171 to 175 °C (340 to 347 °F; 444 to 448 K)
558:
792:
682:
444:
311:
InChI=1S/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
1117:Sergey A. Kozmin, Shuwen He, and Viresh H. Rawal.
554:
421:202 °C (396 °F; 475 K) 2 mmHg
1159:Paul Binger, Petra Wedemann, and Udo H. Brinker.
1241:
566:
221:
1203:"Preparation of n-Butyl 4-Chlorophenyl Sulfide"
95:
1034:, which contains a displaceable methoxy group
664:
1220:: CS1 maint: multiple names: authors list (
1178:: CS1 maint: multiple names: authors list (
1136:: CS1 maint: multiple names: authors list (
852:
656:
264:
181:
159:
260:
1242:
799:, but also in aromatic solvents, like
172:
314:Key: WRIKHQLVHPKCJU-UHFFFAOYSA-N
294:Key: WRIKHQLVHPKCJU-UHFFFAOYSA-N
857:NaHMDS is used as a strong base in
304:Key: WRIKHQLVHPKCJU-JSJAVMDOAQ
212:
13:
695:Potassium bis(trimethylsilyl)amide
14:
1271:
289:InChI=1S/C6H18NSi2.Na/c1-8(2,3)7-
731:
689:Lithium bis(trimethylsilyl)amide
524:
519:
40:
31:
22:
17:Sodium bis(trimethylsilyl)amide
1052:Metal bis(trimethylsilyl)amides
814:NaHMDS is quickly destroyed by
766:Sodium bis(trimethylsilyl)amide
727:(at 25 °C , 100 kPa).
1194:
1152:
1110:
1080:
1076:10.1002/047084289X.rs071m.pub2
1064:
483:Occupational safety and health
1:
1057:
63:-(trimethylsilyl)silanaminide
829:
807:by virtue of the lipophilic
496:Highly flammable, corrosive
7:
1231:, vol. 10, p. 147
1189:, vol. 10, p. 231
1147:, vol. 10, p. 301
1045:
74:Sodium hexamethyldisilazane
72:Sodium hexamethyldisilazide
10:
1276:
838:, consisting of a central
1250:Bis(trimethylsilyl)amides
853:Applications in synthesis
721:
674:
500:
480:
475:
458:
343:
323:
276:
79:
69:
53:
48:
39:
30:
21:
824:bis(trimethylsilyl)amine
707:Lithium diisopropylamide
579:Precautionary statements
291:9(4,5)6;/h1-6H3;/q-1;+1
59:Sodium 1,1,1-trimethyl-
1260:Non-nucleophilic bases
770:organosilicon compound
861:. Typical reactions:
471:Triangular pyramidal
899:To deprotonation of
55:Preferred IUPAC name
886:dehydrohalogenation
428:Solubility in water
383: g·mol
141:Beilstein Reference
18:
754:Infobox references
675:Related compounds
441:in other solvents
433:Reacts with water
16:
1229:Collected Volumes
1208:Organic Syntheses
1187:Collected Volumes
1166:Organic Syntheses
1145:Collected Volumes
1124:Organic Syntheses
1104:10.1021/om970444c
1098:(23): 5108–5112.
901:phosphonium salts
859:organic synthesis
772:with the formula
762:Chemical compound
760:
759:
716:Potassium hydride
702:Related compounds
549:Hazard statements
335:C(C)(C)N()(C)(C)C
245:CompTox Dashboard
121:Interactive image
1267:
1255:Sodium compounds
1234:
1232:
1225:
1219:
1211:
1198:
1192:
1190:
1183:
1177:
1169:
1156:
1150:
1148:
1141:
1135:
1127:
1114:
1108:
1107:
1084:
1078:
1068:
1041:
1033:
996:
960:
922:NaHMDS converts
848:
820:sodium hydroxide
786:
744:
738:
735:
734:
670:
666:
662:
658:
654:
650:
646:
642:
638:
634:
630:
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
586:
572:
568:
564:
560:
556:
528:
523:
401:0.9 g/cm, solid
391:off-white solid
382:
369:
351:Chemical formula
269:
268:
253:
251:
225:
214:
193:
185:
174:
163:
123:
99:
44:
35:
26:
19:
15:
1275:
1274:
1270:
1269:
1268:
1266:
1265:
1264:
1240:
1239:
1238:
1237:
1227:
1213:
1212:
1199:
1195:
1185:
1171:
1170:
1157:
1153:
1143:
1129:
1128:
1115:
1111:
1091:Organometallics
1085:
1081:
1069:
1065:
1060:
1048:
1039:
1035:
1032:
1028:
1024:
1020:
1016:
1012:
995:
991:
987:
983:
979:
975:
971:
967:
963:
958:
954:
950:
947:+ RX → RN(Si(CH
946:
942:
938:
934:
905:Wittig reagents
865:To deprotonate
855:
847:
843:
839:
832:
785:
781:
777:
773:
763:
756:
751:
750:
749: ?)
740:
736:
732:
728:
714:
710:
703:
693:
691:
685:
581:
551:
537:
516:
493:
468:
466:Molecular shape
451:
430:
380:
368:
364:
360:
356:
353:
339:
336:
331:
330:
319:
316:
315:
312:
306:
305:
302:
296:
295:
292:
290:
284:
283:
272:
254:
247:
228:
215:
203:
166:
143:
126:
113:
102:
89:
75:
73:
65:
64:
12:
11:
5:
1273:
1263:
1262:
1257:
1252:
1236:
1235:
1193:
1151:
1109:
1079:
1062:
1061:
1059:
1056:
1055:
1054:
1047:
1044:
1037:
1030:
1026:
1022:
1018:
1014:
998:
997:
993:
989:
985:
981:
977:
973:
969:
965:
961:
956:
952:
948:
944:
940:
936:
909:
908:
897:
878:
854:
851:
845:
841:
831:
828:
783:
779:
775:
761:
758:
757:
752:
730:
729:
725:standard state
722:
719:
718:
712:Sodium hydride
704:
701:
698:
697:
686:
680:
677:
676:
672:
671:
637:P305+P351+P338
625:P303+P361+P353
617:P301+P330+P331
582:
577:
574:
573:
552:
547:
544:
543:
538:
533:
530:
529:
517:
512:
509:
508:
498:
497:
494:
491:
488:
487:
478:
477:
473:
472:
469:
464:
461:
460:
456:
455:
442:
435:
434:
431:
426:
423:
422:
419:
413:
412:
409:
403:
402:
399:
393:
392:
389:
385:
384:
378:
372:
371:
366:
362:
358:
354:
349:
346:
345:
341:
340:
338:
337:
334:
326:
325:
324:
321:
320:
318:
317:
313:
310:
309:
307:
303:
300:
299:
297:
293:
288:
287:
279:
278:
277:
274:
273:
271:
270:
257:
255:
243:
240:
239:
236:
230:
229:
227:
226:
218:
216:
208:
205:
204:
202:
201:
197:
195:
187:
186:
176:
168:
167:
165:
164:
156:
154:
148:
147:
144:
139:
136:
135:
132:
131:Abbreviations
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
92:
90:
85:
82:
81:
77:
76:
71:
67:
66:
58:
57:
51:
50:
46:
45:
37:
36:
28:
27:
9:
6:
4:
3:
2:
1272:
1261:
1258:
1256:
1253:
1251:
1248:
1247:
1245:
1230:
1223:
1217:
1210:
1209:
1204:
1197:
1188:
1181:
1175:
1168:
1167:
1162:
1155:
1146:
1139:
1133:
1126:
1125:
1120:
1113:
1105:
1101:
1097:
1093:
1092:
1083:
1077:
1073:
1067:
1063:
1053:
1050:
1049:
1043:
1009:
1007:
1003:
1000:where X is a
962:
933:
932:
931:
929:
925:
924:alkyl halides
920:
918:
914:
906:
903:, generating
902:
898:
895:
894:cyclopropenes
891:
890:cyclopropanes
887:
883:
879:
876:
872:
868:
864:
863:
862:
860:
850:
837:
827:
825:
821:
817:
812:
810:
806:
802:
798:
797:diethyl ether
794:
790:
771:
767:
755:
748:
743:
726:
720:
717:
713:
708:
705:
700:
699:
696:
690:
687:
684:
679:
678:
673:
583:
580:
576:
575:
553:
550:
546:
545:
542:
539:
536:
532:
531:
527:
522:
518:
515:
511:
510:
506:
504:
499:
495:
490:
489:
485:
484:
479:
474:
470:
467:
463:
462:
457:
454:
450:
446:
443:
440:
437:
436:
432:
429:
425:
424:
420:
418:
417:Boiling point
415:
414:
410:
408:
407:Melting point
405:
404:
400:
398:
395:
394:
390:
387:
386:
379:
377:
374:
373:
355:
352:
348:
347:
342:
333:
332:
329:
322:
308:
298:
286:
285:
282:
275:
267:
263:
262:DTXSID5061451
259:
258:
256:
246:
242:
241:
237:
235:
232:
231:
224:
220:
219:
217:
211:
207:
206:
199:
198:
196:
194:
189:
188:
184:
180:
177:
175:
173:ECHA InfoCard
170:
169:
162:
158:
157:
155:
153:
150:
149:
145:
142:
138:
137:
133:
130:
129:
122:
118:
117:
115:
111:
106:
105:
98:
94:
93:
91:
88:
84:
83:
78:
68:
62:
56:
52:
47:
43:
38:
34:
29:
25:
20:
1228:
1216:cite journal
1206:
1196:
1186:
1174:cite journal
1164:
1154:
1144:
1132:cite journal
1122:
1112:
1095:
1089:
1082:
1066:
1010:
1004:and R is an
999:
921:
913:cyanohydrins
910:
877:derivatives.
873:to generate
856:
833:
813:
765:
764:
540:
502:
492:Main hazards
481:
80:Identifiers
70:Other names
60:
980:O → O(Si(CH
535:Signal word
486:(OHS/OSH):
388:Appearance
344:Properties
179:100.012.713
1244:Categories
1058:References
514:Pictograms
459:Structure
439:Solubility
376:Molar mass
152:ChemSpider
108:3D model (
87:CAS Number
935:NaN(Si(CH
880:Generate
830:Structure
774:NaN(Si(CH
633:P304+P340
629:P304+P312
621:P302+P352
613:P301+P312
505:labelling
357:NaN(Si(CH
234:UN number
200:213-983-8
192:EC Number
97:1070-89-9
1046:See also
964:RN(Si(CH
882:carbenes
836:trimeric
818:to form
811:groups.
692:(LiHMDS)
476:Hazards
161:21169873
146:3629917
1021:N(Si(CH
1002:halogen
875:enolate
867:ketones
805:toluene
801:benzene
768:is the
747:what is
745: (
683:cations
453:toluene
449:benzene
397:Density
381:183.377
370:
223:2724254
210:PubChem
134:NaHMDS
928:amines
917:thiols
871:esters
849:ring.
742:verify
739:
681:Other
541:Danger
328:SMILES
49:Names
1006:alkyl
992:+ RNH
959:+ NaX
816:water
709:(LDA)
281:InChI
238:3263
110:JSmol
1222:link
1180:link
1138:link
915:and
892:and
869:and
822:and
803:and
789:base
669:P501
665:P405
661:P363
657:P330
653:P322
649:P321
645:P312
641:P310
609:P280
605:P273
601:P271
597:P270
593:P264
589:P261
585:P260
571:H412
567:H332
563:H314
559:H312
555:H302
1100:doi
1072:doi
1042:–.
1017:OCH
976:+ H
926:to
884:by
809:TMS
795:or
793:THF
503:GHS
445:THF
250:EPA
213:CID
1246::
1226:;
1218:}}
1214:{{
1205:.
1184:;
1176:}}
1172:{{
1163:.
1142:;
1134:}}
1130:{{
1121:.
1096:16
1094:.
1036:CH
1013:CH
1008:.
919:.
840:Na
826:.
667:,
663:,
659:,
655:,
651:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
569:,
565:,
561:,
557:,
507::
447:,
1233:.
1224:)
1191:.
1182:)
1149:.
1140:)
1106:.
1102::
1074::
1040:O
1038:3
1031:2
1029:)
1027:3
1025:)
1023:3
1019:2
1015:3
994:2
990:2
988:)
986:3
984:)
982:3
978:2
974:2
972:)
970:3
968:)
966:3
957:2
955:)
953:3
951:)
949:3
945:2
943:)
941:3
939:)
937:3
907:.
896:.
846:3
844:N
842:3
784:2
782:)
780:3
778:)
776:3
737:N
367:2
365:)
363:3
361:)
359:3
252:)
248:(
112:)
61:N
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
amide.png)
amide_Structural_formula_V1.svg)
amide_trimer_from_crystal.png)
