cyanamide

Cyanamide is an organic compound with the formula H2N–CN. It is the simplest member of the cyanamide family, consisting of an amino group attached to a nitrile group. At room temperature it is a white, hygroscopic solid that is soluble in water and many polar solvents. It decomposes on heating and is sensitive to moisture.

Industrial production and occurrence: Cyanamide is manufactured on a large scale as an intermediate in the synthesis of guanidines, dicyandiamide, and various agrochemicals. The common commercial route uses calcium cyanamide (CaCN2), an intermediate produced from calcium carbide and nitrogen. In processing, CaCN2 is converted to cyanamide through hydrolysis and purification, yielding a product suitable for further chemical synthesis.

Chemical properties and handling: Cyanamide is a versatile building block in organic synthesis. It participates in condensation and cyclization reactions that form guanidines and related nitrogen-rich heterocycles; it also serves as a precursor to dicyandiamide. It is reactive toward electrophiles and can form stable adducts with various reagents. Storage should be in a dry, well-ventilated place, away from moisture and incompatibles. It is irritating to the skin, eyes, and respiratory tract; exposure should be minimized and appropriate personal protective equipment used.

Applications: In industry, cyanamide is used to produce dicyandiamide and guanidines; it serves as a building block for agrochemicals, polymers, and pharmaceutical intermediates.

Safety and regulation: Cyanamide is toxic and potentially hazardous in concentrated forms. It should be handled under appropriate controls and disposed of according to local regulations.

See also: Calcium cyanamide; Dicyandiamide; Guanidine.