CH2NH2

CH2NH2 is a chemical notation that commonly denotes the aminomethyl group, -CH2NH2, a functional substituent consisting of a methylene carbon attached to an amino group. In this usage, it is not a discrete standalone molecule but a fragment found in a wide range of organic compounds. The aminomethyl group is best recognized in benzylamines, such as benzylamine (Ph-CH2-NH2), where the group is linked to an aromatic ring through the methylene carbon. The presence of the amino group endows the molecule with basic, nucleophilic character, as the nitrogen can be protonated to form ammonium salts and participate in acylation and other reactions; the methylene carbon also offers a site for further transformations.

Synthesis and occurrence: In synthetic chemistry, the aminomethyl group can be introduced via reductive amination of aldehydes or ketones with ammonia or ammonium sources, or through nucleophilic substitution of benzyl halides with ammonia or amines. It frequently appears in pharmaceuticals, agrochemicals, and dyes as part of benzylamine derivatives and related structures.

Reactivity and applications: Amine functionality makes these compounds versatile building blocks for further chemical elaboration, including amide formation, alkylation, and various coupling reactions. The -CH2NH2 moiety can influence solubility, basicity, and binding properties in biological contexts, contributing to the utility of aminomethyl-containing molecules in medicinal chemistry.

Safety: Amine-containing compounds can be irritants and possess characteristic odors; appropriate handling and ventilation are advised.

See also: Methylene group, Methylamine, Benzyl group, Benzylamine, Aminomethylation.