Hydroxymethylamine

Hydroxymethylamine, also called aminomethanol, is the simple amino alcohol with formula CH5NO and structure HO-CH2-NH2. It consists of a hydroxyl and an amino group attached to the same carbon atom. The compound is usually encountered as a reactive intermediate rather than a stable isolated material.

Preparation and occurrence: Hydroxymethylamine is typically generated in situ by combining formaldehyde with ammonia or aqueous ammonia solutions. In many reactions involving formaldehyde and ammonia, hydroxymethylamine forms transiently and either equilibrates with formaldehyde and ammonia or proceeds to further products. It is difficult to purify because it readily polymerizes or decomposes.

Stability and reactions: Hydroxymethylamine is prone to decomposition to formaldehyde and ammonia, especially upon heating or catalysis. In aqueous solution, it is in equilibrium with CH2O and NH3 and can participate as a nucleophile at the amino group or as a source of the hydroxymethyl moiety in subsequent reactions, such as formation of ureas or other amination products under appropriate conditions.

Applications: In practice, hydroxymethylamine is mainly of interest as a reactive intermediate in aldehyde–amine chemistry and in some synthetic sequences where in situ generation of amine–alcohol functionality is desired.

Safety: It is a reactive, irritant compound and should be handled with appropriate protective equipment. It can release ammonia and formaldehyde under certain conditions, and thus should be prepared and used in ventilated facilities.