Cyanamide

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug in Canada, Europe, and Japan. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2). Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug in Canada, Europe, and Japan. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2). Containing both a nucleophilic and electrophilic site within the same molecule, cyanamide undergoes various reactions with itself. Cyanamide exists as two tautomers, one with the connectivity N≡C–NH2 and the other with the formula HN=C=NH ('carbodiimide' tautomer). The N≡C–NH2 form dominates, but in a few reactions (e.g. silylation) the diimide form appears to be important. Cyanamide dimerizes to give 2-cyanoguanidine (dicyandiamide). This dimerization is disfavored by acids and is inhibited by low temperatures. The cyclic trimer is called melamine. Cyanamide is produced by hydrolysis of calcium cyanamide, which in turn is prepared from calcium carbide via the Frank-Caro process.