carbonitrile

Carbonitrile, commonly referred to as a nitrile, is an organic compound featuring the cyano group (-C≡N) bonded to a carbon skeleton. The general formula is R-CN, where R denotes an alkyl or aryl group. The simplest member is acetonitrile (ethanenitrile, CH3-CN), with many other examples such as benzonitrile (Ph-CN) and propionitrile (CH3CH2-CN). The cyano group is linear and highly polar, contributing to the characteristic reactivity and solvent properties of nitriles.

Nitriles are versatile in chemistry. They are typically obtained or synthesized by methods such as substitution of alkyl halides with cyanide salts, dehydration of amides, or conversion of aldehydes or ketones to cyanohydrins followed by dehydration. They can be hydrolyzed under acidic or basic conditions to yield carboxylic acids (or their salts) and ammonia or ammonium in the process. Reduction of nitriles, using hydrogenation or hydride reagents, affords primary amines (R-CH2-NH2). Nitriles can also participate in various carbon–carbon bond-forming reactions and can serve as synthetic intermediates in pharmaceuticals, agrochemicals, and materials.

Applications of nitriles are broad. Acetonitrile is a widely used polar aprotic solvent in chromatography and synthesis. Acrylonitrile, produced from propene, is a key monomer for polyacrylonitrile polymers used in fibers and plastics. Other nitriles serve as intermediates for fragrances, dyes, and agrochemicals.

Safety and handling considerations are important, as many nitriles can be toxic and may release toxic species upon degradation or metabolism. Proper ventilation and standard chemical-handling precautions are advised.