Benzylamine

Benzylamine is the chemical compound with the formula C6H5CH2NH2. It consists of a benzyl group, C6H5CH2, attached to an amine functional group. This colorless liquid is a common precursor in organic synthesis.

Benzylamine is preprared by hydrogenation of benzonitrile.


 * Benzonitrile hydrogenation.svg

It is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis:
 * C6H5CH2NH2 +  2 RBr  →   C6H5CH2NR2  +  2 HBr
 * C6H5CH2NR2 +  H2  →   C6H5CH3  +  R2NH

Typically a base is employed in the first step to absorb the HBr (or related acid for other kinds of alkylating agents).