2-Furonitrile

Synthesis

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).

Applications

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.

References

References

1. P. A. Pavlov. (1986). "Synthesis of 5-substituted furannitriles and their reaction with hydrazine". Khimiya Geterotsiklicheskikh Soedinenii.
2. Patrice Capdevielle. (1989). "Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles". Synthesis.
3. Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
4. Chenjie Zhu. (2010). "Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent". Synthesis.
5. (2006). "Organic Reactions in Water: Transformation of Aldehydes to Nitriles using NBS under Mild Conditions". Synthetic Communications.
6. Sachin S. Chaudhari. (1999). "Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles". Synthetic Communications.
7. A. Narsaiah. (2006). "Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes". Synthetic Communications.
8. (2011). "A general and convenient route to oxazolyl ligands". Tetrahedron Letters.
9. Jacqueline A. Campbell. (2007). "Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions". Synthesis.
10. Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)