Aminomalononitrile

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

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]

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

This easy conversion has been the source of some confusion.

References

^ Ruiz-Bermejo, Marta; Zorzano, María-Paz; Osuna-Esteban, Susana (2013). "Simple Organics and Biomonomers Identified in HCN Polymers: An Overview". Life. 3 (3): 421–448. Bibcode:2013Life....3..421R. doi:10.3390/life3030421. PMC 4187177. PMID 25369814.
^ Ferris, J. P.; Sanchez, R. A.; Mancuso, R. W. (1968). "Aminomalononitrile p-Toluenesulfonate". Organic Syntheses. 48: 1. doi:10.15227/orgsyn.048.0001.

[1] Ruiz-Bermejo, Marta; Zorzano, María-Paz; Osuna-Esteban, Susana (2013). "Simple Organics and Biomonomers Identified in HCN Polymers: An Overview". Life. 3 (3): 421–448. Bibcode:2013Life....3..421R. doi:10.3390/life3030421. PMC 4187177. PMID 25369814.

[2] Ferris, J. P.; Sanchez, R. A.; Mancuso, R. W. (1968). "Aminomalononitrile p-Toluenesulfonate". Organic Syntheses. 48: 1. doi:10.15227/orgsyn.048.0001.

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