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
Appearance	colorless solid
Density	1.234 g/cm3
Melting point	32 °C (90 °F; 305 K)
Boiling point	110–112 °C (230–234 °F; 383–385 K) 20 torr
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 with the formula C₂H₂(CN)₂.^[1] It is a simple unsaturated dinitrile, an isomer of fumaronitrile, which has trans cyanide groups.

Preparation and reactions

The compound was originally prepared by dehydration of maleamide (a derivative of maleic acid) using phosphorus pentoxide.^[2]

Maleonitrile is an electrophilic alkene and a good dienophile.^[3] It participates in metal-catalyzed alkene metathesis reactions.^[4]

Interstellar occurrence

Maleonitrile was detected from interstellar cloud TMC-1 by its spectral emissions.^[5]^[6]

References

1 2 3 "(2Z)-2-Butenedinitrile". PubChem. National Center for Biotechnology Information. Retrieved 13 May 2026.
↑ de Wolf, J.; van de Straete, L. (1935). "Maleonitrile et Fumaronitrile" [Maleonitrile and Fumaronitrile.]. Bulletin de la Classe des Sciences, Academie Royale de Belgique. 21: 216-25.{{cite journal}}: CS1 maint: multiple names: authors list (link)
↑ Dewar, Michael J. S.; Olivella, Santiago.; Stewart, James J. P. (1986). "Mechanism of the Diels-Alder reaction: Reactions of butadiene with ethylene and cyanoethylenes". Journal of the American Chemical Society. 108 (19): 5771–5779. doi:10.1021/ja00279a018. PMID 22175326.
↑ Mu, Yucheng; Nguyen, Thach T.; Koh, Ming Joo; Schrock, Richard R.; Hoveyda, Amir H. (2019). "E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis". Nature Chemistry. 11 (5): 478–487. doi:10.1038/s41557-019-0233-x. PMC 6538264. PMID 30936524.
↑ 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.

[PubChem-1] 1 2 3 "(2Z)-2-Butenedinitrile". PubChem. National Center for Biotechnology Information. Retrieved 13 May 2026.

[2] Wolf, J.; van de Straete, L. (1935). "Maleonitrile et Fumaronitrile" [Maleonitrile and Fumaronitrile.]. Bulletin de la Classe des Sciences, Academie Royale de Belgique. 21: 216-25.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Dewar, Michael J. S.; Olivella, Santiago.; Stewart, James J. P. (1986). "Mechanism of the Diels-Alder reaction: Reactions of butadiene with ethylene and cyanoethylenes". Journal of the American Chemical Society. 108 (19): 5771–5779. doi:10.1021/ja00279a018. PMID 22175326.

[4] Mu, Yucheng; Nguyen, Thach T.; Koh, Ming Joo; Schrock, Richard R.; Hoveyda, Amir H. (2019). "E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis". Nature Chemistry. 11 (5): 478–487. doi:10.1038/s41557-019-0233-x. PMC 6538264. PMID 30936524.

[5] 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.

[6] 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.

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