Diaminomaleonitrile (DAMN) is an organic compound composed of two amino groups and two nitrile groups bonded to a central alkene unit. The systematic name reflects its relationship to maleic acid. DAMN forms by oligomerization of hydrogen cyanide. It is the starting point for the synthesis of several classes of heterocyclic compounds. It has been considered as a possible organic chemical present in prebiotic conditions.
Diaminomaleonitrile (DAMN) is an organic compound composed of two amino groups and two nitrile groups bonded to a central alkene unit. The systematic name reflects its relationship to maleic acid. DAMN forms by oligomerization of hydrogen cyanide. It is the starting point for the synthesis of several classes of heterocyclic compounds. It has been considered as a possible organic chemical present in prebiotic conditions.
== Isolation and synthesis == Diaminomaleonitrile was first isolated in 1873 as an impure black solid, when it was recognized as a derivative of hydrogen cyanide with the formula (HCN)x. It was identified as the tetramer (HCN)4 by ebullioscopy in 1923. The cis-configuration of the amino groups was shown in 1928 through reaction with glyoxal to give , and the full structure was shown in 1955 to be diaminomaleonitrile, as opposed to the isomeric aminoiminosuccinonitrile (AISN). 282x282px It can be prepared by cyanation of aminomalononitrile.
Discovered by embedding cosine similarity (sentence-transformers MiniLM, 384-dim).