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407852 Sigma-Aldrich

tert-Butyldimethylsilyl cyanide

97%

Synonym: tert-Butyl-cyano-dimethylsilane

  • CAS Number 56522-24-8

  • Linear Formula (CH3)3CSi(CH3)2CN

  • Molecular Weight 141.29

  •  Beilstein/REAXYS Number 2234709

  •  MDL number MFCD00054923

  •  PubChem Substance ID 24865490

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C6 to C7, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds - Organic Building Blocks,
Quality Level   100
assay   97%
mp   76-79 °C (lit.)
SMILES string   CC(C)(C)[Si](C)(C)C#N
InChI   1S/C7H15NSi/c1-7(2,3)9(4,5)6-8/h1-5H3
InChI key   CWAKIXKDPQTVTA-UHFFFAOYSA-N

Description

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.

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGI
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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