8606. Sodium Cyanoborohydride

Nomenclature

CAS number: 25895-60-7
Sodium (cyano-C)trihydroborate(1); sodium borocyanohydride; sodium cyanohydridoborate.
CH3BNNa; mol wt 62.84.
C 19.11%, H 4.81%, B 17.20%, N 22.29%, Na 36.58%.
NaBH3CN.

Description and references

Reducing agent prepared from NaBH4 and HCN: R. C. Wade et al., Inorg. Chem. 9, 2146 (1970); R. C. Wade, DE 2028569 corresp to US 3667923 (1971, 1972 both to Ventron). Review of prepn, properties and use: C. F. Lane, Synthesis 1975, 135-146.

Properties

White, hygroscopic powder, mp 240-242° (dec). d28 1.199. Soly (g/100 g solvent) in water (29°): 212; in THF (28°): 37.2; in diglyme (25°): 17.6. Very sol in methanol; slightly sol in ethanol, isopropylamine; insol in ethyl ether, benzene, hexane. Stable in acid to pH 3; undergoes rapid hydrolysis in 12N HCl. Rate of hydrolysis 108 that of NaBH4.

Use

Selective reducing agent for aldehydes, ketones, oximes, enamines; does not reduce amides, ethers, lactones, nitriles, nitro compds and epoxides. Also used for reductive amination of ketones and aldehydes, reductive alkylation of amines and hydrazines, reductive displacement of halides and tosylates, deoxygenation of aldehydes and ketones. See Lane, loc. cit.