Fumaronitrile

Fumaronitrile
Names
	Other names (2E)-2-Butenedinitrile
Identifiers
CAS Number	764-42-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1451833;
ChemSpider	553503;
ECHA InfoCard	100.011.020
EC Number	212-122-3;
PubChem CID	637930;
UN number	3439
CompTox Dashboard (EPA)	DTXSID7025342 ;
	InChI InChI=1S/C4H2N2/c5-3-1-2-4-6/h1-2H/b2-1+ Key: KYPOHTVBFVELTG-OWOJBTEDSA-N;
	SMILES C(=C/C#N)\C#N;
Properties
Chemical formula	C4H2N2
Molar mass	78.074 g·mol−1
Appearance	white solid
Density	1.249 g/cm3
Melting point	96.8 °C (206.2 °F; 369.9 K)
Boiling point	48 °C (118 °F; 321 K) 4 torr
Hazards
	GHS labelling:
Pictograms	‹ The template below (GHS skull and crossbones) is being considered for merging with GHS pictogram. See templates for discussion to help reach a consensus. ›
Signal word	Danger
Hazard statements	H301, H331
Precautionary statements	P261, P264, P270, P271, P301+P316, P304+P340, P316, P321, P330, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Fumaronitrile is an organic compound with the formula C₂H₂(CN)₂. It is a simple unsaturated dinitrile, an isomer of maleonitrile, which has cis cyanide groups.

Preparation and reactions

The compound was originally prepared by dehydration of the diamide of fumaric acid using phosphorus pentoxide.^[2]

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

References

↑ PubChem. "Fumaronitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-08-23.
↑ Keiser, E. H.; Kessler, J. J. (1912). "The Nitrile of Fumaric Acid". American Chemical Journal. 48: 523-8.{{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. Bibcode:1986JAChS.108.5771D. 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. Bibcode:2019NatCh..11..478M. doi:10.1038/s41557-019-0233-x. PMC 6538264. PMID 30936524.

[1] PubChem. "Fumaronitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-08-23.

[2] Keiser, E. H.; Kessler, J. J. (1912). "The Nitrile of Fumaric Acid". American Chemical Journal. 48: 523-8.{{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. Bibcode:1986JAChS.108.5771D. 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. Bibcode:2019NatCh..11..478M. doi:10.1038/s41557-019-0233-x. PMC 6538264. PMID 30936524.

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Preparation and reactions

References