7677-24-9

Description

Trimethylsilane cyanide is a colorless volatile liquid with almond odor, soluble in most organic solvents, such as dichloromethane, chloroform, etc.; it reacts violently with protic solvents such as water. This compound is used in organic synthesis as a replacement reagent for highly toxic HCN to introduce cyano groups into molecules. Trimethylsilyl cyanide (TMSCN) is a commercial reagent used as cyanide source for nucleophilic reactions. It is a clear colorless to yellow liquid, moisture sensitive, with a boiling point of 114–117 °C, which was first synthetized by the reaction of trimethylsilicon halides TMSX and AgCN in 1952.TMSCN is a versatile reagent that can be used in several different reactions, but it is generally used in nucleophilic additions to aldehydes, ketones and imines to form cyanohydrin silyl ethers (Scheme 1a) and α-aminonitriles in Strecker-type reactions (Scheme 1b).Reactions of Trimethylsilyl Cyanide

Uses

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).