Sodium Cyanoborohydride
Title: Sodium Cyanoborohydride
CAS Registry Number: 25895-60-7
CAS Name: Sodium (cyano-C)trihydroborate(1-)
Additional Names: sodium borocyanohydride; sodium cyanohydridoborate
Molecular Formula: CH3BNNa
Molecular Weight: 62.84
Percent Composition: C 19.11%, H 4.81%, B 17.20%, N 22.29%, Na 36.58%
Line Formula: NaBH3CN
Literature 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 10-8 that of NaBH4.
Melting point: mp 240-242° (dec)
Density: d28 1.199
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.

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