Diaminomaleonitrile

Diaminomaleonitrile
Names
	IUPAC name (Z)-2,3-Diaminobut-2-enedinitrile
	Other names 2,3-Diaminomaleonitrile; Hydrogen cyanide tetramer
Identifiers
CAS Number	1187-42-4;
3D model (JSmol)	Interactive image;
ChemSpider	2006128;
ECHA InfoCard	100.013.361
PubChem CID	2723951;
CompTox Dashboard (EPA)	DTXSID0024923 ;
	InChI InChI=1S/C4H4N4/c5-1-3(7)4(8)2-6/h7-8H2/b4-3- Key: DPZSNGJNFHWQDC-ARJAWSKDSA-N;
	SMILES C(#N)/C(=C(\C#N)/N)/N;
Properties
Chemical formula	C4H4N4
Molar mass	108.104 g·mol−1
Melting point	178–179 °C (352–354 °F; 451–452 K)[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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.

The chemical can be formed by polymerization of hydrogen cyanide and can be used as the starting point for the synthesis of several classes of heterocyclic compounds. Therefore, it has been considered as a possible organic chemical present in prebiotic conditions.[2]

References

"Diaminomaleonitrile". Sigma-Aldrich.
Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. (2003). "The Chemistry of Diaminomaleonitrile and its Utility in Heterocyclic Synthesis". Tetrahedron. 59 (16): 2749–2763. doi:10.1016/S0040-4020(03)00153-4.

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[1] "Diaminomaleonitrile". Sigma-Aldrich.

[2] Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. (2003). "The Chemistry of Diaminomaleonitrile and its Utility in Heterocyclic Synthesis". Tetrahedron. 59 (16): 2749–2763. doi:10.1016/S0040-4020(03)00153-4.