Amines
Amines can be prepared from haloalkanes and can be further alkylated to quaternary ammonium compounds.
- Functional group
- C-N
Overview
Nitrogen nucleophiles and precursors to ammonium salts.
Amines can be prepared from haloalkanes and can be further alkylated to quaternary ammonium compounds.
The nitrogen lone pair makes amines bases and nucleophiles. Protonation gives ammonium ions; alkylation forms carbon-nitrogen bonds. Their relative basicity depends on substituents and solvent, so one universal primary/secondary/tertiary ranking is misleading.
Identifiers
- Functional group
- C-N
Chemical identifiers
- SMILES
- CCN
Properties
- Acid-base change
- Protonation is reversible and changes charge without adding carbon.
- Acylation boundary
- Primary and secondary amines can form neutral amides; tertiary amines lack an N-H bond and are often used as bases.
Related compounds
- Methylamine
A primary amine that forms methylammonium salts on protonation.
- Ethylamine
A primary alkylamine that acts as both a base and a nucleophile.
- Propylamine
Propan-1-amine, a primary amine with a three-carbon chain.
- Isopropylamine
Isopropylamine is an organic compound with the molecular formula C3H9N.
- Dimethylamine
A secondary amine with two methyl groups and one N–H bond.
- Trimethylamine
A tertiary amine with a nitrogen lone pair but no N–H bond.
- Diethylamine
Diethylamine is an organic compound with the molecular formula C4H11N.
- Triethylamine
A tertiary organic base with three ethyl groups attached to nitrogen.
- Benzylamine
Benzylamine is an organic compound with the molecular formula C7H9N.
- Ethylenediamine
A two-carbon diamine with an amino group at each end.
Connected reactions
- Amination: Chloroalkanes → Amines
Ammonia substitutes chloride to form a primary amine; excess ammonia limits further alkylation.
- Amination: Bromoalkanes → Amines
Ammonia substitutes bromide to form a primary amine; excess ammonia limits further alkylation.
- Amination: Iodoalkanes → Amines
Ammonia substitutes iodide to form a primary amine; excess ammonia limits further alkylation.
- Alkylation: Amines → Quaternary ammonium compounds
Amines can be further alkylated to permanent cationic quaternary ammonium groups used in antimicrobial and ion-exchange materials.
- Reduction: Nitriles → Amines
Nitriles can be reduced to primary amines, separating the amine feedstock route from later amide or materials chemistry.
- Acylation co reactant: Amines → N-substituted amides
Amines are acylated by acyl chlorides to form N-substituted amides.
- Weak base equilibrium: Amines → Aqueous alkylammonium ions
Amines are weak bases in water and form alkylammonium and hydroxide ions.
- Salt formation: Amines → Amine salts
Amines react with acids to form alkylammonium salts.
- Copper(II) complex formation: Amines → Copper-amine complexes
Amines react with aqueous copper(II) ions and form a deep-blue complex in excess amine.
References
- Organic Chemistry: Basicity of AminesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.
- Organic Chemistry: Chemistry of Acid HalidesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports acid-halide preparation with thionyl chloride and nucleophilic acyl substitution chemistry, including tetrahedral intermediates, hydrolysis, alcoholysis and amine acylation at acid chlorides.
- PubChem Compound Summary: Methylamine (CID 6329)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Ethylamine (CID 6341)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Propylamine (CID 7852)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Isopropylamine (CID 6363)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Dimethylamine (CID 674)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Trimethylamine (CID 1146)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Diethylamine (CID 8021)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Triethylamine (CID 8471)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Benzylamine (CID 7504)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Ethylenediamine (CID 3301)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.