Trimethylsilyl cyanide #CAS7677-24-9

Trimethylsilyl cyanide #CAS7677-24-9

TMSCN, chemically known as Trimethylsilylcyanide or Cyanotrimethylsilane, is a colorless liquid with an almond-like taste. It is soluble in most organic solvents, such as dichloromethane and chloroform, but reacts violently with proton-containing solvents such as water.

Application of Trimethylsilyl cyanide

Cyanotrimethylsilane is a highly versatile reagent that reacts with a multitude of functional groups to yield an array of products and/or highly valuable synthetic intermediates. Aldehydes and ketones are readily transformed into the corresponding cyanohydrin trimethylsilyl ethers when treated with cyanotrimethylsilane in the presence of Lewis acids (eq 1), triethylamine,or solid bases such as CaF2 or hydroxyapatite. The products can be readily hydrolyzed to the corresponding cyanohydrins. The cyanosilylation of aromatic aldehydes can be achieved with high enantioselectivity in the presence of catalytic amounts of a modified Sharpless catalyst consisting of titanium tetraisopropoxide and L-(+)-diisopropyl tartrate (eq 2).Catalysis with chiral titanium reagents yields aliphatic and aromatic cyanohydrins in high chemical and optical yields (eq 3). Cyanohydrins can be subsequently transformed into a variety of useful synthetic intermediates (eq 4).

Trimethylsilyl Cyanide is used as a reagent in the synthesis of optically active cyanohydrins. Used in the preparation of Reissert compounds, which represent reactive polyamides. Toxic to humans.

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