Aminomalononitrile

Aminomalononitrile (AMN) is the organic compound with the formula . As the name indicates, it can be viewed as an amine-substituted malononitrile.

AMN is of some interest to the study of the chemical origin of life because it represents a trimer of HCN, speculated to be a progenitor of nucleic acids.

Aminomalononitrile has been prepared by reduction of the oxime with aluminium amalgam. The compound can be used in situ or isolated as the tosylate salt ( where -OTs is ):

AMN reacts with cyanide to give diaminomaleonitrile, a tetramer of HCN:

This easy conversion has been the source of some confusion.

References