2-Furonitrile
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| Names | |
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IUPAC name
furan-2-carbonitrile
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| Other names
2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.581 |
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PubChem CID
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| Properties | |
| C5H3NO | |
| Molar mass | 93.09 g·mol−1 |
| Appearance | colorless (yellow if impure) |
| Density | 1.0650 @20 °C |
| Boiling point | 147 °C (297 °F; 420 K) |
| Hazards | |
| Flash point | 35 °C; 95 °F; 308 K |
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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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| Infobox references | |
2-Furonitrile is a colorless derivative of furan possessing a nitrile group.
Industrial synthesis is based on the vapor phase ammoxidation of furfural with ammonia over bismuth molybdate catalyst at 440-480 °C.
Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with ammonia salts using hypervalent iodine reagents or n-bromosuccinimide. From furfural aldoxime (with thionyl chloride-benzotriazole, triphenylphosphine-iodine reagents, or heating in DMSO) and furoic acid amide (flash vacuum pyrolysis).
2-Furonitrile currently has no major applications but it is used as an intermediate in pharmaceutical and fine chemical synthesis. It has been suggested as a potential sweetening agent, as it has about thirty times the sweetening power of sucrose.
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