Maleonitrile
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| Names | |
|---|---|
| IUPAC name
(Z)-but-2-enedinitrile | |
| Preferred IUPAC name
(2Z)-2-Butenedinitrile | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| EC Number |
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PubChem CID |
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| Properties | |
| 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) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]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
[edit]Maleonitrile was detected from interstellar cloud TMC-1 by its spectral emissions.[5][6]
References
[edit]- 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.