Cyanogen chloride

Cyanogen chloride is an inorganic compound with the formula NCCl. This linear, triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is widely used in biochemical analysis and preparation.

Synthesis, basic properties, structure

Cyanogen chloride is a molecule with the connectivity ClCN. Carbon and chlorine are linked by a single bond, and carbon and nitrogen by a triple bond. It is a linear molecule, as are the related cyanogen halides (NCF, NCBr, NCI). Cyanogen chloride is produced by the oxidation of sodium cyanide with chlorine. This reaction proceeds via the intermediate cyanogen ((CN)₂).

The compound trimerizes in the presence of acid to the heterocycle called cyanuric chloride.

Cyanogen chloride is slowly hydrolyzed by water to release cyanate and chloride ions

Applications in synthesis

Cyanogen chloride is a precursor to the sulfonyl cyanides and chlorosulfonyl isocyanate, a useful reagent in organic synthesis.