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Names | |
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Preferred IUPAC name Furan-2-carbonitrile | |
Other names 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.009.581 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C5H3NO | |
Molar mass | 93.085 g·mol−1 |
Appearance | colorless (yellow if impure) |
Density | 1.0650 @20 °C [1] |
Boiling point | 147 [2] °C (297 °F; 420 K) |
Hazards | |
Flash point | 35 °C; 95 °F; 308 K |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [3]
Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with ammonia salts using hypervalent iodine reagents [4] or n-bromosuccinimide. [5] From furfural aldoxime (with thionyl chloride-benzotriazole, [6] triphenylphosphine-iodine reagents, [7] or heating in DMSO [8] ) and furoic acid amide (flash vacuum pyrolysis). [9]
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 30 times the sweetening power of sucrose. [10]