Nitriles
Nitriles made from haloalkanes are useful intermediates because they can be reduced to amines or hydrolysed to carboxylic acids.
- Functional group
- C≡N
Overview
Cyanide-derived intermediates that add one carbon to the chain.
Nitriles made from haloalkanes are useful intermediates because they can be reduced to amines or hydrolysed to carboxylic acids.
The carbon in a nitrile group is part of the molecular carbon skeleton. Replacing a haloalkane leaving group with cyanide therefore adds one carbon; subsequent hydrolysis or reduction preserves that enlarged skeleton. Hydrolysis passes through an amide, while reduction gives a primary amine.
Identifiers
- Functional group
- C≡N
Chemical identifiers
- SMILES
- CC#N
Properties
- Connectivity
- Organic nitrile: R-C≡N; this is different from an isocyanide, R-N≡C.
- Hydrolysis product
- Acidic hydrolysis gives the carboxylic acid; alkaline hydrolysis gives a carboxylate until acid work-up.
Related compounds
- Acrylonitrile
One of the three monomers used to make ABS.
- Acetonitrile
A polar aprotic solvent whose nitrile group is also a reaction site.
- Propanenitrile
A three-carbon nitrile that retains its nitrile carbon in hydrolysis and reduction.
- Benzonitrile
Benzonitrile is an organic compound with the molecular formula C7H5N.
- Butanenitrile
A four-carbon nitrile whose terminal nitrile carbon is included in the chain length.
- 2-Hydroxypropanenitrile
The cyanohydrin of ethanal, with hydroxyl and nitrile groups attached to the same carbon.
- 2-Hydroxy-2-methylpropanenitrile
The cyanohydrin of propanone, retaining two equivalent methyl groups.
Connected reactions
- Cyanation: Chloroalkanes → Nitriles
Cyanide substitution forms a nitrile and extends the carbon chain by one carbon.
- Cyanation: Bromoalkanes → Nitriles
Cyanide substitution forms a nitrile and extends the carbon chain by one carbon.
- Cyanation: Iodoalkanes → Nitriles
Cyanide substitution forms a nitrile and extends the carbon chain by one carbon.
- Hydrolysis: Nitriles → Carboxylic acids
Nitriles can be hydrolysed to carboxylic acids, splitting the old aggregate nitrile-to-amide route into a single functional-group conversion.
- Reduction: Nitriles → Amines
Nitriles can be reduced to primary amines, separating the amine feedstock route from later amide or materials chemistry.
References
- Organic Chemistry: Chemistry of NitrilesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports nitrile reduction by two hydride additions to imine-anion and aluminium-stabilised dianion intermediates, followed by aqueous work-up to a primary amine; also documents nitrile hydrolysis through amide intermediates.
- ABS: monomers and manufacturing routesINEOS
- PubChem Compound Summary: Acetonitrile (CID 6342)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Propanenitrile (CID 7854)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Benzonitrile (CID 7505)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Butanenitrile (CID 8008)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.
- PubChem Compound Summary: 2-Hydroxypropanenitrile (CID 6572)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.
- PubChem Compound Summary: 2-Hydroxy-2-methylpropanenitrile (CID 6406)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.