Aminoacetaldehyde

Aminoacetaldehyde is a small organic molecule that contains both an amino group and an aldehyde group. The simplest form has the structure H2N-CH2-CHO, making it the two‑carbon amino aldehyde. As such, it is a reactive intermediate rather than a isolable, stable compound under ordinary conditions.

In practice, aminoacetaldehyde is usually generated in situ or used as a transient intermediate in chemical syntheses. It can be prepared by mild oxidation of 2‑aminoethanol (ethanolamine) or by other selective oxidation routes. In biological and prebiotic chemistry contexts, aminoacetaldehyde has been discussed as a possible intermediate in the processing of amino alcohols and in pathways related to amino acids and related metabolites.

The molecule’s reactivity reflects its dual functionality: the amino group can participate in nucleophilic reactions, while the aldehyde group can undergo nucleophilic addition and condensation to form Schiff bases. As a reactive aldehyde amine, aminoacetaldehyde tends to form imines with carbonyl partners and can be oxidized or reduced under appropriate conditions. Because of this reactivity, it is typically handled with care and is not usually stored for extended periods.

Overall, aminoacetaldehyde serves as a useful but highly reactive building block in organic synthesis and as a point of discussion in studies of amino alcohol metabolism and prebiotic chemistry.