51:
61:
310:
191:
538:
533:
518:
528:
523:
758:
753:
757:
865:
759:
38:
1108:
756:
1868:
1617:
974:
1979:
1250:
781:
2049:"The use of polystyrylsulfonyl chloride resin as a solid supported condensation reagent for the formation of esters: Synthesis of N--L-aspartic acid; α tert-butyl ester, β-(2-ethylphenyl]amino]ethyl ester"
546:
1726:
498:
774:
1743:
1453:
2073:
Stephanie Ganss; Julia
Pedronl; Alexandre Lumbroso; Günther Leonhardt-Lutterbeck; Antje Meißner; Siping Wei; Hans-Joachim Drexler; Detlef Heller; Bernhard Breit (2016).
680:
50:
839:
1131:
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in
60:
843:
672:
1888:
1142:
878:
1999:
2131:
2032:
1103:{\displaystyle x\ {\ce {MeCl + Si}}\longrightarrow {\begin{cases}{\ce {Me3SiCl}},\\{\ce {Me2SiCl2}},\\{\ce {MeSiCl3}},\\{\text{etc.}}\end{cases}}}
1870:
Using this approach, atmospheric nitrogen can be introduced into organic substrate. For example, tris(trimethylsilyl)amine reacts with α,δ,ω-tri
1649:
833:
349:
1358:
Trimethylsilyl chloride also reacts with carbanions to give trimethylsilyl derivatives. Lithium acetylides react to give trimethylsilyl
873:
676:
2260:
2170:
608:
788:
2153:
Philip
Boudjouk; Jeung-Ho So (1992). "Solvated and Unsolvated Anhydrous Metal Chlorides from Metal Chloride Hydrates".
2016:
1003:
960:, but substantial amounts of the trimethyl and monomethyl products are also obtained. The relevant reactions are (Me =
938:. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
2265:
324:
767:
1446:
Dehydration of metal chlorides with trimethylsilyl chloride in THF gives the solvate as illustrated by the case of
2105:
885:
1323:
the original functional group by removing the labile protons and decreasing the basicity of the heteroatom. The
148:
1363:
594:
257:
186:
2072:
1399:. Despite their hydrolytic instability, these compounds have found wide application in organic chemistry;
288:
652:
537:
2026:
604:
532:
660:
1729:
198:
2192:
1643:
1435:
1374:
813:
720:
305:
24:
460:
517:
2270:
1635:
957:
905:
2108:"One-Carbon Ring Expansion of Cycloalkanones to Conjugated Cycloalkenone: 2-Cyclohepten-1-one"
522:
2125:
1863:{\displaystyle {\ce {3 Me3SiCl + 3 Li}}+{\tfrac {1}{2}}\,{\ce {N2 -> (Me3Si)3N + 3 LiCl}}}
1631:
847:
620:
560:
510:
20:
2106:
Yoshihiko Ito, Shotaro Fujii, Masashi
Nakatuska, Fumio Kawamoto, and Takeo Saegusa (1979).
1737:
1642:, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). These compounds are produced by a
1639:
1612:{\displaystyle {\ce {CrCl3 * 6 H2O + 12 Me3SiCl -> CrCl3(THF)3 + 6 (Me3Si)2O + 12 HCl}}}
1447:
1281:
1136:
527:
266:
80:
2075:"Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters"
1252:
The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce
696:
664:
168:
8:
1420:
684:
114:
309:
190:
124:
2180:
1882:
1348:
628:
482:
2212:
2166:
2112:
2053:
2012:
1257:
19:"TMCS" redirects here. For the history of Ticketmaster Online–CitySearch (TMCS), see
2158:
2086:
2004:
1320:
688:
448:
372:
1412:
1265:
953:
644:
230:
2207:
2107:
2048:
616:
2162:
1424:
1393:
1344:
1313:
1112:
Typically about 2–4% of the product stream is the monochloride, which forms an
948:
856:
724:
636:
632:
2254:
2091:
2074:
2008:
1370:
648:
437:
427:
179:
37:
1626:
Trimethylsilyl chloride is used to prepare other trimethylsilyl halides and
656:
1627:
909:
780:
716:
1408:
1404:
1309:
802:
787:
700:
766:
704:
668:
1646:
between trimethylsilyl chloride and a salt of the (pseudo)halide (MX):
1427:
1396:
1297:
1285:
1132:
773:
692:
391:
199:
159:
956:
with a silicon-copper alloy. The principal target of this process is
712:
1400:
1253:
1113:
600:
578:
277:
1347:
can also be used to increase the volatility of a compound, enabling
855:
Except where otherwise noted, data are given for materials in their
1974:{\displaystyle {\ce {2 Me3SiCl + 2 Na -> 2 NaCl + Me3Si-SiMe3}}}
1733:
1416:
1381:
1343:
groups allow them to be easily removed afterwards ("deprotected").
1324:
1301:
1245:{\displaystyle {\ce {2 Me3SiCl + H2O -> Me3Si-O-SiMe3 + 2 HCl}}}
739:
732:
147:
1875:
1431:
1359:
1352:
1269:
640:
413:
217:
1997:
Röshe, L.; John, P.; Reitmeier, R. "Organic
Silicon Compounds".
566:
23:. For the Turtle Mountain Community School in North Dakota, see
2046:
1871:
1385:
1280:. Similarly, trimethylsilyl chloride is also used to silanize
1277:
1273:
961:
1996:
1308:
readily undergo reaction with trimethylsilyl chloride, giving
1630:, including trimethylsilyl fluoride, trimethylsilyl bromide,
1389:
1316:
1305:
1261:
241:
137:
612:
293:
54:
Ball-and-stick model of the trimethylsilyl chloride molecule
1378:
1096:
64:
Space-filling model of the trimethylsilyl chloride molecule
2152:
1366:. Such derivatives are useful protected forms of alkynes.
624:
574:
2241:
Silicon in
Organic, Organometallic, and Polymer Chemistry
2205:
1967:
1946:
1907:
1843:
1827:
1806:
1762:
1721:{\displaystyle {\ce {MX + Me3Si-Cl -> MCl + Me3Si-X}}}
1703:
1670:
1592:
1576:
1551:
1530:
1511:
1488:
1468:
1228:
1199:
1180:
1161:
1077:
1055:
1042:
1017:
586:
1783:
1891:
1746:
1652:
1456:
1260:
in alcohols, which find use in the mild synthesis of
1145:
977:
2243:. New York: John Wiley & Sons. pp. 193–194.
1728:
TMSCl, lithium, and nitrogen molecule react to give
1973:
1862:
1720:
1611:
1291:
1244:
1102:
16:Organosilicon compound with the formula (CH3)3SiCl
2252:
570:
229:
755:
123:
2000:Ullmann's Encyclopedia of Industrial Chemistry
728:
582:
2130:: CS1 maint: multiple names: authors list (
2031:: CS1 maint: multiple names: authors list (
1351:of normally nonvolatile substances such as
1881:Reduction of trimethylsilyl chloride give
946:TMSCl is prepared on a large scale by the
708:
308:
189:
167:
2090:
1929:
1919:
1896:
1855:
1794:
1774:
1751:
1604:
1560:
1500:
1477:
1237:
1150:
265:
2047:Norbert Zander and Ronald Frank (2005).
304:
2253:
821:400 °C (752 °F; 673 K)
807:−28 °C (−18 °F; 245 K)
432:−40 °C (−40 °F; 233 K)
180:
2238:
1990:
1126:
442:57 °C (135 °F; 330 K)
408:Colorless liquid, fumes in moist air
336:Key: IJOOHPMOJXWVHK-UHFFFAOYSA-N
21:IAC (company) § 1980s and 1990s
1415:can be used to return the original
333:InChI=1S/C3H9ClSi/c1-5(2,3)4/h1-3H3
220:
13:
2206:L. Birkofer and P. Wegner (1970).
2157:. Vol. 29. pp. 108–111.
1621:
1300:, polar functional groups such as
751:
59:
49:
14:
2282:
863:
536:
531:
526:
521:
516:
36:
1441:
1423:group at the alpha carbon. The
1292:Silylation in organic synthesis
859:(at 25 °C , 100 kPa).
2261:Reagents for organic chemistry
2232:
2199:
2146:
2099:
2066:
2039:
1923:
1833:
1814:
1809:
1684:
1582:
1563:
1541:
1535:
1517:
1186:
995:
941:
1:
1983:
1364:bis(trimethylsilyl)acetylene
7:
2227:, vol. 6, p. 1030
1430:can also be used as masked
1284:, making the surfaces more
45:
10:
2287:
2239:Brook, Michael A. (2000).
2163:10.1002/9780470132609.ch26
2141:, vol. 1, p. 327
18:
1730:tris(trimethylsilyl)amine
853:
825:
497:
492:
475:
365:
345:
320:
107:
91:
79:
74:
44:
35:
2266:Trimethylsilyl compounds
2092:10.15227/orgsyn.093.0367
2009:10.1002/14356007.a24_021
1644:salt metathesis reaction
1436:Mukaiyama aldol addition
1375:lithium diisopropylamide
595:Precautionary statements
31:Trimethylsilyl chloride
25:Belcourt School District
2003:. Weinheim: Wiley-VCH.
898:Trimethylsilyl chloride
840:Trimethylsilyl fluoride
461:Magnetic susceptibility
94:Trimethylsilyl chloride
85:Chlorotri(methyl)silane
2208:"Trimethylsilyl azide"
1975:
1864:
1722:
1636:trimethylsilyl cyanide
1613:
1246:
1104:
958:dimethyldichlorosilane
906:organosilicon compound
844:Trimethylsilyl bromide
762:
65:
55:
1976:
1865:
1732:, under catalysis by
1723:
1632:trimethylsilyl iodide
1614:
1310:trimethylsilyl ethers
1247:
1105:
902:chlorotrimethylsilane
848:Trimethylsilyl iodide
761:
100:Trimethylchlorosilane
96:Chlorotrimethylsilane
63:
53:
1889:
1744:
1738:chromium trichloride
1650:
1640:trimethylsilyl azide
1454:
1448:chromium trichloride
1282:laboratory glassware
1143:
1137:hexamethyldisiloxane
975:
924:, often abbreviated
912:), with the formula
744:(fire diamond)
81:Preferred IUPAC name
2155:Inorganic Syntheses
1969:
1948:
1909:
1845:
1829:
1808:
1764:
1705:
1672:
1594:
1578:
1553:
1532:
1513:
1490:
1470:
1434:equivalents in the
1369:In the presence of
1345:Trimethylsilylation
1319:. These new groups
1230:
1201:
1182:
1163:
1079:
1057:
1044:
1019:
449:Solubility in water
400:g/mol
32:
1971:
1957:
1936:
1897:
1883:hexamethyldisilane
1874:to give tricyclic
1860:
1817:
1812:
1796:
1792:
1752:
1718:
1693:
1660:
1609:
1566:
1561:
1533:
1520:
1501:
1478:
1458:
1349:gas chromatography
1296:By the process of
1242:
1218:
1189:
1170:
1151:
1127:Reactions and uses
1100:
1095:
1067:
1045:
1032:
1007:
952:, the reaction of
886:Infobox references
826:Related compounds
763:
488:Tetrahedral at Si
66:
56:
30:
2225:Collected Volumes
2213:Organic Syntheses
2172:978-0-470-13260-9
2139:Collected Volumes
2113:Organic Syntheses
2054:Organic Syntheses
2027:cite encyclopedia
1960:
1951:
1939:
1932:
1922:
1912:
1900:
1858:
1848:
1832:
1820:
1799:
1791:
1777:
1767:
1755:
1716:
1708:
1696:
1689:
1683:
1675:
1663:
1656:
1607:
1597:
1581:
1569:
1540:
1523:
1516:
1504:
1493:
1481:
1461:
1392:are converted to
1258:hydrochloric acid
1240:
1221:
1212:
1204:
1192:
1185:
1173:
1166:
1154:
1091:
1070:
1048:
1035:
1022:
1010:
993:
987:
983:
894:Chemical compound
892:
891:
561:Hazard statements
289:CompTox Dashboard
149:Interactive image
70:
69:
2278:
2245:
2244:
2236:
2230:
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1509:
1502:
1491:
1489:
1486:
1479:
1469:
1466:
1459:
1342:
1334:
1266:carboxylic acids
1251:
1249:
1248:
1243:
1241:
1238:
1229:
1226:
1219:
1217:
1210:
1209:
1202:
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1197:
1190:
1183:
1181:
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1162:
1159:
1152:
1122:
1109:
1107:
1106:
1101:
1099:
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1080:
1078:
1075:
1068:
1058:
1056:
1053:
1046:
1043:
1040:
1033:
1023:
1020:
1018:
1015:
1008:
994:
991:
985:
981:
970:
932:
923:
900:, also known as
876:
870:
867:
866:
792:
791:
783:
776:
769:
754:
734:
730:
726:
722:
718:
714:
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706:
702:
698:
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690:
686:
682:
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662:
658:
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646:
642:
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602:
588:
584:
580:
576:
572:
568:
540:
535:
530:
525:
520:
470:
421:
399:
373:Chemical formula
313:
312:
297:
295:
269:
233:
222:
201:
193:
182:
171:
151:
127:
46:
40:
33:
29:
2286:
2285:
2281:
2280:
2279:
2277:
2276:
2275:
2251:
2250:
2249:
2248:
2237:
2233:
2223:
2204:
2200:
2188:
2187:
2178:
2177:
2173:
2151:
2147:
2137:
2123:
2122:
2104:
2100:
2071:
2067:
2044:
2040:
2024:
2023:
2019:
1995:
1991:
1986:
1966:
1961:
1952:
1945:
1940:
1906:
1901:
1892:
1890:
1887:
1886:
1842:
1837:
1826:
1821:
1813:
1805:
1800:
1795:
1782:
1761:
1756:
1747:
1745:
1742:
1741:
1709:
1702:
1697:
1676:
1669:
1664:
1653:
1651:
1648:
1647:
1624:
1622:Other reactions
1591:
1586:
1575:
1570:
1562:
1550:
1545:
1534:
1529:
1524:
1510:
1505:
1487:
1482:
1467:
1462:
1457:
1455:
1452:
1451:
1444:
1413:dihydroxylation
1340:
1336:
1332:
1328:
1294:
1227:
1222:
1213:
1205:
1198:
1193:
1179:
1174:
1160:
1155:
1146:
1144:
1141:
1140:
1129:
1121:
1117:
1094:
1093:
1088:
1085:
1084:
1076:
1071:
1066:
1063:
1062:
1054:
1049:
1041:
1036:
1031:
1028:
1027:
1016:
1011:
1006:
999:
998:
984:
976:
973:
972:
969:
965:
954:methyl chloride
944:
930:
926:
921:
917:
913:
895:
888:
883:
882:
881: ?)
872:
868:
864:
860:
846:
842:
836:
818:
815:
797:
796:
795:
794:
789:
785:
778:
771:
764:
760:
752:
597:
563:
549:
513:
485:
483:Molecular shape
468:
464:
451:
419:
397:
385:
381:
375:
361:
358:
353:
352:
341:
338:
337:
334:
328:
327:
316:
298:
291:
272:
252:
236:
223:
211:
174:
154:
141:
130:
117:
103:
101:
99:
97:
95:
87:
86:
28:
17:
12:
11:
5:
2284:
2274:
2273:
2268:
2263:
2247:
2246:
2231:
2198:
2189:|journal=
2171:
2145:
2098:
2065:
2038:
2018:978-3527306732
2017:
1988:
1987:
1985:
1982:
1964:
1955:
1943:
1935:
1928:
1925:
1918:
1915:
1904:
1895:
1854:
1851:
1840:
1835:
1824:
1816:
1811:
1803:
1790:
1787:
1781:
1773:
1770:
1759:
1750:
1712:
1700:
1692:
1686:
1679:
1667:
1659:
1623:
1620:
1603:
1600:
1589:
1584:
1573:
1565:
1559:
1556:
1548:
1543:
1537:
1527:
1519:
1508:
1499:
1496:
1485:
1476:
1473:
1465:
1443:
1440:
1425:trimethylsilyl
1419:group with an
1394:trimethylsilyl
1338:
1330:
1314:trimethylsilyl
1293:
1290:
1236:
1233:
1225:
1216:
1208:
1196:
1188:
1177:
1169:
1158:
1149:
1128:
1125:
1119:
1097:
1087:
1086:
1083:
1074:
1065:
1064:
1061:
1052:
1039:
1030:
1029:
1026:
1014:
1005:
1004:
1002:
997:
990:
980:
967:
949:direct process
943:
940:
928:
919:
915:
893:
890:
889:
884:
862:
861:
857:standard state
854:
851:
850:
837:
831:
828:
827:
823:
822:
819:
812:
809:
808:
805:
799:
798:
786:
779:
772:
765:
750:
749:
748:
747:
745:
736:
735:
681:P305+P351+P338
673:P303+P361+P353
665:P301+P330+P331
598:
593:
590:
589:
564:
559:
556:
555:
550:
545:
542:
541:
514:
509:
506:
505:
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494:
490:
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486:
481:
478:
477:
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2271:Chlorosilanes
2269:
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1628:pseudohalides
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1371:triethylamine
1367:
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438:Boiling point
436:
435:
431:
429:
428:Melting point
426:
425:
422:g/cm, liquid
417:
415:
412:
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404:
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395:
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389:
377:
374:
370:
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364:
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306:DTXSID2024822
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181:ECHA InfoCard
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26:
22:
2240:
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2217:
2211:
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2154:
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2126:cite journal
2117:
2111:
2101:
2082:
2078:
2068:
2058:
2052:
2041:
1998:
1992:
1880:
1625:
1445:
1442:Dehydrations
1368:
1357:
1295:
1272:as well as,
1135:to give the
1130:
1111:
947:
945:
935:
925:
910:silyl halide
901:
897:
896:
814:Autoignition
740:
552:
499:
242:RTECS number
108:Identifiers
92:Other names
2085:: 367–384.
2045:Such as in
1428:enol ethers
1409:epoxidation
1405:double bond
1397:enol ethers
942:Preparation
834:halosilanes
816:temperature
803:Flash point
547:Signal word
405:Appearance
386:SiCl
366:Properties
187:100.000.819
2255:Categories
2079:Org. Synth
1984:References
1379:enolisable
1298:silylation
1286:lipophilic
1133:hydrolysis
511:Pictograms
476:Structure
392:Molar mass
267:62UO4690X6
160:ChemSpider
136:3D model (
115:CAS Number
2191:ignored (
2181:cite book
1954:−
1924:⟶
1810:⟶
1711:−
1685:⟶
1678:−
1518:⟶
1472:⋅
1401:oxidation
1382:aldehydes
1321:"protect"
1254:anhydrous
1215:−
1207:−
1187:⟶
1114:azeotrope
996:⟶
725:P403+P235
721:P403+P233
717:P370+P378
685:P308+P313
677:P304+P340
669:P302+P352
661:P301+P310
502:labelling
467:−77.36·10
357:C(C)(C)Cl
278:UN number
249:VV2710000
208:200-900-5
200:EC Number
1876:pyrroles
1736:wire or
1734:nichrome
1417:carbonyl
1362:such as
1325:lability
1302:alcohols
1270:nitriles
832:Related
741:NFPA 704
493:Hazards
463:(χ)
1872:ketones
1432:enolate
1421:alcohol
1403:of the
1386:ketones
1360:alkynes
1353:glucose
1327:of the
1278:ketones
1274:acetals
879:what is
877: (
471:cm/mol
454:Reacts
414:Density
218:PubChem
125:75-77-4
2169:
2015:
1390:esters
1317:amines
1306:amines
1262:esters
1118:MeSiCl
1069:MeSiCl
982:
962:methyl
904:is an
874:verify
871:
553:Danger
469:
420:
398:
396:108.64
350:SMILES
75:Names
2220:: 107
2120:: 113
2061:: 235
1276:from
1264:from
1116:with
936:TMSCl
418:0.856
325:InChI
282:1298
138:JSmol
98:TMSCl
2193:help
2167:ISBN
2132:link
2033:link
2013:ISBN
1959:SiMe
1931:NaCl
1911:SiCl
1857:LiCl
1766:SiCl
1522:CrCl
1515:SiCl
1460:CrCl
1388:and
1373:and
1341:Si−N
1335:and
1333:Si−O
1312:and
1304:and
1268:and
1220:SiMe
1165:SiCl
1090:etc.
1047:SiCl
1021:SiCl
986:MeCl
931:SiCl
922:SiCl
733:P501
729:P405
713:P363
709:P330
705:P322
701:P321
697:P312
693:P311
689:P310
657:P281
653:P280
649:P271
645:P270
641:P264
637:P261
633:P260
629:P243
625:P242
621:P241
617:P240
613:P233
609:P210
605:P202
601:P201
587:H351
583:H331
579:H314
575:H312
571:H301
567:H225
258:UNII
231:6397
169:6157
102:TMCS
2159:doi
2087:doi
2005:doi
1688:MCl
1634:,
1606:HCl
1539:THF
1411:or
1407:by
1355:.
1239:HCl
971:):
934:or
914:(CH
500:GHS
294:EPA
221:CID
2257::
2222:;
2218:50
2216:.
2210:.
2185::
2183:}}
2179:{{
2165:.
2136:;
2128:}}
2124:{{
2118:59
2116:.
2110:.
2083:93
2081:.
2077:.
2059:81
2057:.
2051:.
2029:}}
2025:{{
2011:.
1950:Si
1938:Me
1921:Na
1899:Me
1885::
1878:.
1831:Si
1819:Me
1776:Li
1754:Me
1740::
1707:Si
1695:Me
1682:Cl
1674:Si
1662:Me
1655:MX
1638:,
1602:12
1580:Si
1568:Me
1503:Me
1498:12
1450::
1438:.
1384:,
1377:,
1337:Me
1329:Me
1288:.
1203:Si
1191:Me
1153:Me
1139::
1123:.
1034:Me
1009:Me
992:Si
966:CH
964:,
927:Me
731:,
727:,
723:,
719:,
715:,
711:,
707:,
703:,
699:,
695:,
691:,
687:,
683:,
679:,
675:,
671:,
667:,
663:,
659:,
655:,
651:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
585:,
581:,
577:,
573:,
569:,
504::
2229:.
2195:)
2175:.
2161::
2143:.
2134:)
2095:.
2089::
2063:.
2035:)
2021:.
2007::
1963:3
1942:3
1934:+
1927:2
1917:2
1914:+
1903:3
1894:2
1853:3
1850:+
1847:N
1839:3
1834:)
1823:3
1815:(
1802:2
1798:N
1789:2
1786:1
1780:+
1772:3
1769:+
1758:3
1749:3
1715:X
1699:3
1691:+
1666:3
1658:+
1599:+
1596:O
1588:2
1583:)
1572:3
1564:(
1558:6
1555:+
1547:3
1542:)
1536:(
1526:3
1507:3
1495:+
1492:O
1484:2
1480:H
1475:6
1464:3
1339:3
1331:3
1235:2
1232:+
1224:3
1211:O
1195:3
1184:O
1176:2
1172:H
1168:+
1157:3
1148:2
1120:3
1082:,
1073:3
1060:,
1051:2
1038:2
1025:,
1013:3
1001:{
989:+
979:x
968:3
929:3
920:3
918:)
916:3
908:(
869:Y
790:W
782:2
775:3
768:3
384:9
382:H
380:3
378:C
296:)
292:(
140:)
27:.
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