Cyanogen Bromide - Synthesis, Basic Properties, and Structure

Synthesis, Basic Properties, and Structure

Although the formula is most commonly written CNBr, the carbon atom is actually bonded to bromine by a single bond and to nitrogen by a triple bond (i.e. Br–C≡N). The compound is linear and quite polar, but it does not spontaneously ionize in water. Therefore, it dissolves in both water and polar organic solvents.

Cyanogen bromide can be prepared by oxidation of sodium cyanide with bromine, which proceeds in two steps via the intermediate cyanogen ((CN)2 or N≡C–C≡N).

2 NaCN + Br2 → (CN)2 + 2 NaBr
(CN)2 + Br2 → 2 BrCN

Cyanogen bromide is hydrolyzed by water to release hydrogen cyanide and hypobromous acid

BrCN + H2O → HCN + HOBr

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