737:
212:
139:
392:
382:
24:
387:
577:
789:
Mio, Matthew J.; Kopel, Lucas C.; Braun, Julia B.; Gadzikwa, Tendai L.; Hull, Kami L.; Brisbois, Ronald G.; Markworth, Christopher J.; Grieco, Paul A. (2002). "One-Pot
Synthesis of Symmetrical and Unsymmetrical Bisarylethynes by a Modification of the Sonogashira Coupling Reaction".
400:
362:
502:
590:
494:
879:
268:
498:
893:
H. G. Viehe (1959), "Heterosubstituierte
Acetylene, III. Nucleophile Substitutionen und Halogen-Metall-Austauschreaktionen an Dreifachbindungen",
450:
773:
668:
932:
226:
486:
694:
Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds:
597:
444:
190:
722:
534:
391:
922:
146:
462:
88:
522:
518:
381:
703:
510:
736:
386:
134:
852:
Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1987). "1,4-Bis(trimethylsilyl)buta-1,3-diyne".
613:
470:
927:
873:
688:
659:. Using this protected alkyne, as opposed to acetylene itself, prevents further coupling reactions. The
414:
374:
709:
Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of
660:
652:
506:
36:
207:
54:
458:
895:
538:
474:
482:
829:
809:
769:
680:
676:
640:
553:
900:
861:
834:
801:
761:
699:
530:
291:
514:
116:
792:
672:
490:
64:
211:
138:
721:
Trimethylsilylacetylene was first synthesized in 1959 by Heinz Günter Viehe. He reduced
23:
568:
632:. A colorless liquid, "tms acetylene", as it is also called, is used as a source of "
916:
730:
726:
710:
695:
347:
127:
756:
Godson C. Nwokogu; Saskia
Zemolka; Florian Dehme (2007). "Trimethylsilylacetylene".
546:
683:
Sonogashira coupling, in which the phenylacetylene derivative reacts with a second
478:
765:
420:
178:
684:
436:
559:
526:
454:
316:
107:
904:
865:
838:
432:
656:
633:
466:
813:
428:
827:
Andrew B. Holmes, Chris N. Sporikou (1987). "Trimethylsilylacetylene".
337:
165:
147:
805:
424:
687:
after in-situ deprotection. A less expensive alternative reagent is
567:
Except where otherwise noted, data are given for materials in their
87:
77:
675:
derivatives. Trimethylsilylacetylene is also used to synthesize
664:
542:
899:(in German), vol. 92, no. 12, pp. 3064–3075,
735:
195:
585:
691:, which after alkynylation is deprotected with base.
177:
63:
8:
878:: CS1 maint: multiple names: authors list (
733:and proceeded with subsequent hydrolysis.
210:
137:
115:
15:
627:
623:
619:
748:
273:
252:InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
245:InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
235:InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
231:
206:
871:
128:
352:53 °C (127 °F; 326 K)
255:Key: CWMFRHBXRUITQE-UHFFFAOYSA-N
238:Key: CWMFRHBXRUITQE-UHFFFAOYSA-N
7:
651:Trimethylsilylacetylene is used in
168:
14:
575:
390:
385:
380:
303:
22:
723:chloro(trimethylsilyl)acetylene
571:(at 25 °C , 100 kPa).
309:
297:
1:
766:10.1002/047084289X.rt288.pub2
663:can then be cleaved off with
702:, followed by reaction with
949:
565:
361:
356:
284:
264:
222:
47:
35:
30:
21:
933:Trimethylsilyl compounds
905:10.1002/cber.19590921209
866:10.15227/orgsyn.065.0052
839:10.15227/orgsyn.065.0061
445:Precautionary statements
41:Ethynyltri(methyl)silane
17:Trimethylsilylacetylene
704:trimethylsilyl chloride
610:Trimethylsilylacetylene
740:
614:organosilicon compound
739:
689:2-methylbut-3-yn-2-ol
655:as the equivalent of
653:Sonogashira couplings
698:of acetylene with a
661:trimethylsilyl group
37:Preferred IUPAC name
324: g·mol
18:
896:Chemische Berichte
741:
598:Infobox references
16:
923:Ethynyl compounds
854:Organic Syntheses
830:Organic Syntheses
806:10.1021/ol026266n
800:(19): 3199–3202.
775:978-0-471-93623-7
725:by reaction with
679:derivatives in a
677:diphenylacetylene
641:organic synthesis
616:with the formula
606:Chemical compound
604:
603:
554:Safety data sheet
415:Hazard statements
332:colorless liquid
191:CompTox Dashboard
89:Interactive image
940:
908:
907:
890:
884:
883:
877:
869:
849:
843:
841:
824:
818:
817:
786:
780:
779:
753:
700:Grignard reagent
631:
588:
582:
579:
578:
548:
544:
540:
536:
532:
528:
524:
520:
516:
512:
508:
504:
500:
496:
492:
488:
484:
480:
476:
472:
468:
464:
460:
456:
452:
438:
434:
430:
426:
422:
394:
389:
384:
323:
311:
305:
299:
292:Chemical formula
215:
214:
199:
197:
181:
170:
149:
141:
130:
119:
91:
67:
26:
19:
948:
947:
943:
942:
941:
939:
938:
937:
913:
912:
911:
892:
891:
887:
870:
851:
850:
846:
826:
825:
821:
793:Organic Letters
788:
787:
783:
776:
755:
754:
750:
746:
719:
673:phenylacetylene
649:
637:
629:
625:
621:
617:
607:
600:
595:
594:
593: ?)
584:
580:
576:
572:
447:
417:
403:
377:
321:
308:
302:
294:
280:
277:
272:
271:
260:
257:
256:
253:
247:
246:
240:
239:
236:
230:
229:
218:
200:
193:
184:
171:
159:
122:
94:
81:
70:
57:
43:
42:
12:
11:
5:
946:
944:
936:
935:
930:
925:
915:
914:
910:
909:
885:
844:
819:
781:
774:
747:
745:
742:
718:
715:
648:
645:
635:
605:
602:
601:
596:
574:
573:
569:standard state
566:
563:
562:
557:
550:
549:
503:P305+P351+P338
495:P303+P361+P353
448:
443:
440:
439:
418:
413:
410:
409:
404:
399:
396:
395:
378:
373:
370:
369:
359:
358:
354:
353:
350:
344:
343:
340:
334:
333:
330:
326:
325:
319:
313:
312:
306:
300:
295:
290:
287:
286:
282:
281:
279:
278:
275:
267:
266:
265:
262:
261:
259:
258:
254:
251:
250:
248:
244:
243:
241:
237:
234:
233:
225:
224:
223:
220:
219:
217:
216:
203:
201:
189:
186:
185:
183:
182:
174:
172:
164:
161:
160:
158:
157:
153:
151:
143:
142:
132:
124:
123:
121:
120:
112:
110:
104:
103:
100:
99:Abbreviations
96:
95:
93:
92:
84:
82:
75:
72:
71:
69:
68:
60:
58:
53:
50:
49:
45:
44:
40:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
945:
934:
931:
929:
926:
924:
921:
920:
918:
906:
902:
898:
897:
889:
886:
881:
875:
867:
863:
859:
855:
848:
845:
840:
836:
832:
831:
823:
820:
815:
811:
807:
803:
799:
795:
794:
785:
782:
777:
771:
767:
763:
759:
752:
749:
743:
738:
734:
732:
731:diethyl ether
728:
727:phenyllithium
724:
716:
714:
712:
711:1,3-butadiyne
707:
705:
701:
697:
696:deprotonation
692:
690:
686:
682:
678:
674:
670:
666:
662:
658:
654:
646:
644:
642:
638:
615:
611:
599:
592:
587:
570:
564:
561:
560:External MSDS
558:
555:
552:
551:
449:
446:
442:
441:
419:
416:
412:
411:
408:
405:
402:
398:
397:
393:
388:
383:
379:
376:
372:
371:
367:
365:
360:
355:
351:
349:
348:Boiling point
346:
345:
341:
339:
336:
335:
331:
328:
327:
320:
318:
315:
314:
296:
293:
289:
288:
283:
274:
270:
263:
249:
242:
232:
228:
221:
213:
209:
208:DTXSID7061435
205:
204:
202:
192:
188:
187:
180:
176:
175:
173:
167:
163:
162:
155:
154:
152:
150:
145:
144:
140:
136:
133:
131:
129:ECHA InfoCard
126:
125:
118:
114:
113:
111:
109:
106:
105:
101:
98:
97:
90:
86:
85:
83:
79:
74:
73:
66:
62:
61:
59:
56:
52:
51:
46:
38:
34:
29:
25:
20:
928:Carbosilanes
894:
888:
874:cite journal
857:
853:
847:
828:
822:
797:
791:
784:
757:
751:
720:
708:
693:
650:
609:
608:
406:
363:
48:Identifiers
685:aryl halide
401:Signal word
329:Appearance
285:Properties
135:100.012.655
917:Categories
744:References
375:Pictograms
342:0.69 g/mL
317:Molar mass
276:C#C(C)(C)C
108:ChemSpider
76:3D model (
55:CAS Number
657:acetylene
539:P403+P235
535:P403+P233
531:P370+P378
523:P337+P313
519:P332+P313
499:P304+P340
491:P302+P352
366:labelling
156:213-919-9
148:EC Number
65:1066-54-2
814:12227748
671:to form
357:Hazards
717:History
681:one-pot
612:is the
591:what is
589: (
338:Density
166:PubChem
860:: 52.
833:: 61.
812:
772:
586:verify
583:
556:(SDS)
407:Danger
322:98.220
269:SMILES
31:Names
639:" in
227:InChI
179:66111
117:59499
102:TMSA
78:JSmol
880:link
810:PMID
770:ISBN
758:EROS
665:TBAF
547:P501
543:P405
527:P362
515:P321
511:P312
507:P310
487:P280
483:P271
479:P264
475:P261
471:P243
467:P242
463:P241
459:P240
455:P233
451:P210
437:H335
433:H319
429:H318
425:H315
421:H225
901:doi
862:doi
835:doi
802:doi
762:doi
729:in
669:DBU
667:or
647:Use
626:SiC
618:(CH
364:GHS
196:EPA
169:CID
919::
876:}}
872:{{
858:65
856:.
808:.
796:.
768:.
760:.
713:.
706:.
643:.
634:HC
545:,
541:,
537:,
533:,
529:,
525:,
521:,
517:,
513:,
509:,
505:,
501:,
497:,
493:,
489:,
485:,
481:,
477:,
473:,
469:,
465:,
461:,
457:,
453:,
435:,
431:,
427:,
423:,
368::
310:Si
307:10
903::
882:)
868:.
864::
842:.
837::
816:.
804::
798:4
778:.
764::
636:2
630:H
628:2
624:3
622:)
620:3
581:Y
304:H
301:5
298:C
198:)
194:(
80:)
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