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212849 Sigma-Aldrich

Trimethylsilyl cyanide

98%

Synonym: Cyanotrimethylsilane, TMSCN

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Properties

Related Categories Building Blocks, C1 to C5, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds - Organic Building Blocks,
InChI Key   LEIMLDGFXIOXMT-UHFFFAOYSA-N
assay   98%
refractive index   n20/D 1.392 (lit.)
bp   114-117 °C(lit.)
mp   8-11 °C (lit.)
density   0.793 g/mL at 20 °C (lit.)

Description

General description

Trimethylsilyl cyanide participates in carbonyl aminomethylation via α-silyloxy nitriles.

Application

Trimethylsilyl cyanide was used:
• for derivatization of complex metabolite mixtures by GC-MS
• as cyanide source in enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones
• as reagent for the cyanosilylation of aldehydes in near quantitative yield via catalysis by silylene-bridged rare earth oxide complexes
• in asymmetric cyanosilylation with chiral dinuclear Ti(IV) complexes

Packaging

25 g in Sure/Seal™

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
Contact with water liberates toxic gas.
RIDADR 
UN 3384 3(6.1) / PGI
WGK Germany 
3
Flash Point(F) 
33.8 °F
Flash Point(C) 
1 °C

Documents

Certificate of Analysis

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Certificate of Origin

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Protocols & Articles

Articles

Acids and Bases

Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This product line ranges from Brønsted and Lewis acids, ...
Chemfiles Volume 1 Article 3

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used al...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers
15

References

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