Cyanogen bromide
Cyanogen bromide is a pseudohalogen compound with the formula C(Br)N. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds.
Synthesis, basic properties, and structure
The carbon atom in cyanogen bromide is 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).
If properly stored the pure material is long-term stable but like other cyanogen compounds it can undergo an exothermic trimerisation to form cyanuric bromide (c.f. cyanuric chloride). This reaction can be catalyzed by traces of bromine, metal salts, acids and bases.
Cyanogen bromide is hydrolyzed by water to release hydrogen cyanide and hypobromous acid
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