nitrile

Article

44 sections

Contents

Structure and basic properties
History
Nomenclature
Differentiation from related compounds
From organic halides and cyanide salts
Hydrocyanation
Dehydration of amides and others
Preparation from aldehydes and ketones
Oxidation of primary amines
Ammoxidation
Preparation of aromatic nitriles
Preparation of cyanohydrins
Preparation of acyl cyanides
Enantioselective synthesis of chiral nitriles
Other methods
Reactions
Hydrolysis
Reduction
Deprotonation
Nucleophiles
Miscellaneous methods and compounds
Complexation
Nitrile derivatives
Organic cyanamides
Nitrile oxides
Occurrence
Occurrence in plants
Nitriles from glucosinolates in cruciferous plants
Cyanohydrins and cyanogenic glycosides
Occurrence in animals
Occurrence in fungi
Occurrence in bacteria
Occurrence in space
Significance for the origin of life
Use
Use of hydrogen cyanide
Plastics production
Chemical-pharmaceutical industry and laboratories
Nitriles in medicine
Pharmaceuticals
Other uses
See also
References
External links

thumb|class=skin-invert-image|The structure of a nitrile: the functional group is highlighted blue

In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called "propionitrile" (or propanenitrile). The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.