Aminomalononitrile

Aminomalononitrile (AMN) is the organic compound with the formula H₂NCH(CN)₂. The compound can be viewed as an amine-substituted malononitrile. It 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.^[1] Aminomalononitrile has been prepared by reduction of the oxime: HONC=(CN)₂ with aluminium amalgam. The compound is used in situ but can be isolated as its tosylate salt [H₃NCH(CN)₂]OTs where ^-OTs is CH₃C₆H₄SO−3.^[2]

Aminomalononitrile

Names
Other names 2-aminomalononitrile, AMN
Identifiers
CAS Number	5181-05-5
3D model (JSmol)	Interactive image
ChemSpider	133313
PubChem CID	151258
CompTox Dashboard (EPA)	DTXSID40199760
InChI InChI=1S/C3H3N3/c4-1-3(6)2-5/h3H,6H2 Key: GXDKXRIMUVUELI-UHFFFAOYSA-N
SMILES C(#N)C(C#N)N
Properties
Chemical formula	C3H3N3
Molar mass	81.078 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

This easy conversion has been the source of some confusion.