// Workers AI · dad joke modeWhat did fumaronitrile say? "I'm bonded to you.
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| Names | |
|---|---|
| Other names
(2E)-2-Butenedinitrile | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.020 |
| EC Number |
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PubChem CID |
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| UN number | 3439 |
CompTox Dashboard (EPA) |
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| Properties | |
| 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:[1] | |
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| Danger | |
| H301, H331 | |
| 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).
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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
[edit]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
[edit]- ↑ 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.