2-Furonitrile
{{Chembox
| Watchedfields = changed
| verifiedrevid = 474954794
| ImageFile = 2-Furonitrile.svg
| ImageSize = 185px
| PIN = Furan-2-carbonitrile
| OtherNames = 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 617-90-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2LRK86H722
| PubChem = 69245
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62458
| SMILES = N#Cc1occc1
| InChI = 1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H
| InChIKey = YXDXXGXWFJCXEB-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YXDXXGXWFJCXEB-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=5 | H=3 | N=1 | O=1
| Appearance = colorless (yellow if impure)
| MeltingPt =
| Solubility =
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPtF = 95
| AutoignitionPtC =
}}
}}
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{{cite journal | author = Chenjie Zhu | title = Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent | journal = Synthesis | volume = 2010| pages = 4235–4241| year = 2010 |last2 = Sun | first2 = Chengguo | last3 = Wei | first3 = Yunyang | issue = 24 | doi=10.1055/s-0030-1258281}} or n-bromosuccinimide.{{cite journal|last1=Bandgar|first1=B. P.|last2=Makone|first2=S. S.|title=Organic Reactions in Water: Transformation of Aldehydes to Nitriles using NBS under Mild Conditions|journal=Synthetic Communications|volume=36|issue=10|year=2006|pages=1347–1352|issn=0039-7911|doi=10.1080/00397910500522009|s2cid=98593006 }} From furfural aldoxime (with thionyl chloride-benzotriazole,{{cite journal | author = Sachin S. Chaudhari | title = Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles | journal = Synthetic Communications | volume = 29 | pages = 1741–1745| year = 1999 |last2 = Akamanchi | first2 = Krishnacharya G. | issue = 10 | doi=10.1080/00397919908086161}} triphenylphosphine-iodine reagents,{{cite journal | author = A. Narsaiah | title = Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes | journal = Synthetic Communications | volume = 36 | pages = 137–140 | year = 2006 |last2 = Sreenu | first2 = D. | last3 = Nagaiah | first3 = K. | issue = 2 | doi=10.1080/00397910500333225}} or heating in DMSO{{cite journal|last1=Aspinall|first1=Helen C.|last2=Beckingham|first2=Oliver|last3=Farrar|first3=Michael D.|last4=Greeves|first4=Nicholas|last5=Thomas|first5=Christopher D.|title=A general and convenient route to oxazolyl ligands|journal=Tetrahedron Letters|volume=52|issue=40|year=2011|pages=5120–5123|issn=0040-4039|doi=10.1016/j.tetlet.2011.07.070}}) and furoic acid amide (flash vacuum pyrolysis).{{cite journal | author = Jacqueline A. Campbell | title = Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions | journal = Synthesis | volume = 2007| pages = 3179–3184| year = 2007 |last2 = McDougald | first2 = Graham | last3 = McNab | first3 = Hamish | issue = 20 | doi=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
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{{DEFAULTSORT:Furonitrile, 2-}}