trimethylsilanecarbonitrile

EN300-29571

Product class

Building Blocks

CAS number

7677-24-9

MW

99.21

Purity

95%

Stock Availability

EU, DE, UA

Lead time

1-5 days delivery time

Reagent for cyanosilylation

Cyanotrimethylsilane is a reagent that enables cyanosilylation of saturated and unsaturated aldehydes and ketones. It colorless liquid with a low boiling point of 118 ℃, which in contact with water produces hydrogen cyanide, but is stable in an inert atmosphere[1]. Soluble in organic solvents (CH2Cl2, CHCl3) but reacts rapidly to any protic solvents. Aldehydes and ketones are readily transformed into the corresponding cyanohydrin trimethylsilyl ethers with high yield when treated with cyanotrimethylsilane in the presence of Lewis acids. Enantioselective and/or diastereoselective formation of cyanohydrins and their derivatives is also possible if the reaction involves chiral ligands and metal catalysts[2]. In addition, cyanotrimethylsilane can be used for cyanation in 1,4-addition with α,β-unsaturated ketones in the presence of base.

Synonyms: trimethylsilyl cyanide; TMSCN

1. Cyanotrimethylsilane. Groutas W. C.; Jin Z.; Zhang H. Encyclopedia of Reagents for Organic Synthesis 2011. DOI: 10.1002/047084289X.rc276 2. Enantioselective Cyanation of Benzylic C–H Bonds via Copper-Catalyzed Radical Relay. Zhang W.; Wang F.; McCann S. D.; Wang D.; Chen P.; Stahl S. S.; Liu G. Science 2016, 353 (6303), 1014–1018. DOI: 10.1126/science.aaf7783

Name:

trimethylsilanecarbonitrile

SMILES:

C[Si](C)(C)C#N

CAS number:

7677-24-9

CLogP:

0.608

ACD number:

MFCD00001765

Dangerous good:

Yes

Class:

Lab Reagents

Formula:

C₄H₉NSi

Subclass:

Nitriles

MW:

99.21

Product class:

Building Blocks