Cyanotrimethylsilane

CAS 7677-24-9, Cat. No EN300-29571
Reagent for cyanosilylation

Cyanotrimethylsilane
EN300-29571

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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

Selected publication

  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

 

 

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