Maleonitrile

Maleonitrile
	Skeletal formula of maleonitrile
Names
	IUPAC name (Z)-but-2-enedinitrile
	Preferred IUPAC name (2Z)-2-Butenedinitrile
	Other names Maleonitrile; Maleinic acid dinitrile;
Identifiers
CAS Number	928-53-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	558876;
EC Number	618-880-5;
PubChem CID	643777;
	InChI InChI=1S/C4H2N2/c5-3-1-2-4-6/h1-2H/b2-1- Key: KYPOHTVBFVELTG-UPHRSURJSA-N;
	SMILES C(=C\C#N)\C#N;
Properties
Chemical formula	C4H2N2
Molar mass	78.074 g·mol−1
Density	1.0 g/cm3
Boiling point	187.3 °C (369.1 °F; 460.4 K)
Hazards
Flash point	82.6 °C (180.7 °F; 355.8 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	20 mg/kg (intraperitoneal, mouse); 40 mg/kg (oral, rat);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Maleonitrile is an organic compound nitrile with the formula C₄H₂N₂.^[1]

Preparation and reactions

It can be prepared by reacting fumaronitrile with a nitrile base such as triethylamine, but any R(CN)x, where x is any positive integer, works. The following reaction diagram can be used.^[3]

fumaronitrile + R(CN)x → maleonitrile + R(CN)x

1 2 3 "(2Z)-2-Butenedinitrile". PubChem. National Center for Biotechnology Information. Retrieved 13 May 2026.
1 2 "(2Z)-2-Butenedinitrile". chemspider.com. ChemSpider. Retrieved 13 May 2026.
↑ US ceased WO1990009370A1, Young, Harold William, Jr., "Isomerization of fumaronitrile to maleonitrile", issued 1990-08-23, assigned to Dow Chemical Co
↑ Agúndez, M.; Bermúdez, C.; Cabezas, C.; Molpeceres, G.; Endo, Y.; Marcelino, N.; Tercero, B.; Guillemin, J.-C.; de Vicente, P.; Cernicharo, J. (August 2, 2024). "The rich interstellar reservoir of dinitriles: Detection of malononitrile and maleonitrile in TMC-1". Astronomy & Astrophysics. 688: L31. arXiv:2408.02843. Bibcode:2024A&A...688L..31A. doi:10.1051/0004-6361/202451525. ISSN 0004-6361.
↑ Victoria Corless (2024-11-12). "Scientists found 'nitriles' in an interstellar cloud — here's why that could be huge". Space.com. Retrieved 2025-01-07.