Acetone imine


Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula 2CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimine. This compound is mainly of academic interest.

Synthesis and reactions

Acetone imine is prepared by dehydrocyanation of the cyanoamine of acetone, which is prepared from acetone cyanohydrin. Dicyclohexylcarbodiimide serves as the scavenger for hydrogen cyanide:
The compound hydrolyzes readily:
This reactivity is characteristic of imines derived from ammonia. Methylene imine is also highly reactive, condensing to hexamethylenetetramine. Upon standing, the imine undergoes further condensation to give the tetrahydropyrimidine called acetonin, with loss of ammonia.
The imine of hexafluoroacetone, is by contrast robust.