2-Furonitrile

changed 474954794 2-Furonitrile.svg 185px Furan-2-carbonitrile 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide correct ?? 617-90-3 correct FDA 2LRK86H722 69245 correct chemspider 62458 N#Cc1occc1 1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H YXDXXGXWFJCXEB-UHFFFAOYAE correct chemspider 1S/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H correct chemspider YXDXXGXWFJCXEB-UHFFFAOYSA-N 5 3 1 1 colorless liquid (yellow if impure) 1.0650 @20 °C P. A. Pavlov Synthesis of 5-substituted furannitriles and their reaction with hydrazine Khimiya Geterotsiklicheskikh Soedinenii 2 181–186 1986 Kul'nevich V. G. 147 Patrice Capdevielle Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles Synthesis 6 451–452 1989 Lavigne Andre Maumy Michel 6 10.1055/s-1989-27285 97316774 95 2-Furonitrile is a colorless derivative of furan possessing a nitrile group. Synthesis Industrial synthesis is based on the vapor phase ammoxidation of furfural with ammonia over bismuth molybdate catalyst at 440–480 °C.Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966) Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with ammonia salts using hypervalent iodine reagents Chenjie Zhu Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent Synthesis 2010 4235–4241 2010 Sun Chengguo Wei Yunyang 24 10.1055/s-0030-1258281 or n-bromosuccinimide.Bandgar B. P. Makone S. S. Organic Reactions in Water: Transformation of Aldehydes to Nitriles using NBS under Mild Conditions Synthetic Communications 36 10 2006 1347–1352 0039-7911 10.1080/00397910500522009 98593006 From furfural aldoxime (with thionyl chloride-benzotriazole, Sachin S. Chaudhari Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles Synthetic Communications 29 1741–1745 1999 Akamanchi Krishnacharya G. 10 10.1080/00397919908086161 triphenylphosphine-iodine reagents, A. Narsaiah Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes Synthetic Communications 36 137–140 2006 Sreenu D. Nagaiah K. 2 10.1080/00397910500333225 or heating in DMSOAspinall Helen C. Beckingham Oliver Farrar Michael D. Greeves Nicholas Thomas Christopher D. A general and convenient route to oxazolyl ligands Tetrahedron Letters 52 40 2011 5120–5123 0040-4039 10.1016/j.tetlet.2011.07.070) and furoic acid amide (flash vacuum pyrolysis). Jacqueline A. Campbell Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions Synthesis 2007 3179–3184 2007 McDougald Graham McNab Hamish 20 10.1055/s-2007-990782 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.Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966) References Category:2-Furyl compounds Category:Nitriles Category:Sugar substitutes