2-Furonitrile
 | |
| Names | |
|---|---|
| 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) |
|
| |
| |
| Properties | |
| C5H3NO | |
| Molar mass | 93.085 g·mol−1 |
| Appearance | colorless liquid (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.
Synthesis
[edit]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]
Applications
[edit]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]
References
[edit]- ↑ P. A. Pavlov; Kul'nevich, V. G. (1986). "Synthesis of 5-substituted furannitriles and their reaction with hydrazine". Khimiya Geterotsiklicheskikh Soedinenii. 2: 181–186.
- ↑ Patrice Capdevielle; Lavigne, Andre; Maumy, Michel (1989). "Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles". Synthesis. 6 (6): 451–452. doi:10.1055/s-1989-27285. S2CID 97316774.
- ↑ Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
- ↑ Chenjie Zhu; Sun, Chengguo; Wei, Yunyang (2010). "Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent". Synthesis. 2010 (24): 4235–4241. doi:10.1055/s-0030-1258281.
- ↑ Bandgar, B. P.; Makone, S. S. (2006). "Organic Reactions in Water: Transformation of Aldehydes to Nitriles using NBS under Mild Conditions". Synthetic Communications. 36 (10): 1347–1352. doi:10.1080/00397910500522009. ISSN 0039-7911. S2CID 98593006.
- ↑ Sachin S. Chaudhari; Akamanchi, Krishnacharya G. (1999). "Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles". Synthetic Communications. 29 (10): 1741–1745. doi:10.1080/00397919908086161.
- ↑ A. Narsaiah; Sreenu, D.; Nagaiah, K. (2006). "Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes". Synthetic Communications. 36 (2): 137–140. doi:10.1080/00397910500333225.
- ↑ Aspinall, Helen C.; Beckingham, Oliver; Farrar, Michael D.; Greeves, Nicholas; Thomas, Christopher D. (2011). "A general and convenient route to oxazolyl ligands". Tetrahedron Letters. 52 (40): 5120–5123. doi:10.1016/j.tetlet.2011.07.070. ISSN 0040-4039.
- ↑ Jacqueline A. Campbell; McDougald, Graham; McNab, Hamish (2007). "Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions". Synthesis. 2007 (20): 3179–3184. doi:10.1055/s-2007-990782.
- ↑ Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)