407852
tert-Butyldimethylsilyl cyanide
97%
Synonym(s):
tert-Butyl-cyano-dimethylsilane
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About This Item
Linear Formula:
(CH3)3CSi(CH3)2CN
CAS Number:
Molecular Weight:
141.29
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2234709
Assay:
97%
InChI
1S/C7H15NSi/c1-7(2,3)9(4,5)6-8/h1-5H3
SMILES string
CC(C)(C)[Si](C)(C)C#N
InChI key
CWAKIXKDPQTVTA-UHFFFAOYSA-N
assay
97%
mp
76-79 °C (lit.)
General description
tert-Butyldimethylsilyl cyanide (TBDMSCN) is a bulkier trialkylsilylcyanide. It participates in the cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes. Addition of TBDMSCN to sterically hindered ketones in the presence of Lewis acid or base catalyst has been studied. ZnI2-catalyzed addition of TBDSCN to 2,2-dimethylcyclohexanone, 2,2,6-trimethylcyclohexanone and 2,2,6,6-tetramethylcyclohexanone affords protected cyanohydrins.
Application
tert-Butyldimethylsilyl cyanide may be used as reagent for the formation of β-isonitrile alcohols via epoxides.
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Danger
hcodes
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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P(RNCH2CH2)N: efficient catalysts for the cyanosilylation of aldehydes and ketones.
Fetterly BM and Verkade JG.
Tetrahedron Letters, 46(46), 8061-8066 (2005)
The Journal of Organic Chemistry, 51, 5010-5010 (1986)
Addition of tert-butyldimethyl-or tert-butyldiphenylsilyl cyanide to hindered ketones.
Golinski M, et al.
The Journal of Organic Chemistry, 58(1), 159-164 (1993)
Benito Alcaide et al.
The Journal of organic chemistry, 72(21), 7980-7991 (2007-09-18)
The cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes with tert-butyldimethylsilyl cyanide was promoted by either molecular sieves or catalytic amount of sodium carbonate to give O-silylated beta-lactam cyanohydrins with good yield and diastereoselectivity. In contrast, Lewis acids did not effectively promote the cyanosilylation
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