| 词条 | 2-Furonitrile |
| 释义 |
| Watchedfields = changed | verifiedrevid = 474954794 | ImageFile = 2-Furonitrile.svg | ImageSize = 185px | IUPACName = furan-2-carbonitrile | OtherNames = 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 617-90-3 | 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) | Density = 1.0650 @20 °C [1] | MeltingPt = | BoilingPtC = 147[2] | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPtF = 95 | AutoignitionPtC = }} 2-Furonitrile is a colorless derivative of furan possessing a nitrile group. SynthesisIndustrial 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] Applications2-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 thirty times the sweetening power of sucrose.[10] References1. ^{{cite journal | author = P. A. Pavlov | title = Synthesis of 5-substituted furannitriles and their reaction with hydrazine | journal = Khimiya Geterotsiklicheskikh Soedinenii | volume = 2 | pages = 181–186 | year = 1986 |last2 = Kul'nevich | first2 = V. G. }} {{DEFAULTSORT:Furonitrile, 2-}}2. ^{{cite journal | author = Patrice Capdevielle | title = Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles | journal = Synthesis | volume = 6 | pages = 451–452 | year = 1989 |last2 = Lavigne | first2 = Andre | last3 = Maumy | first3 = Michel | doi=10.1055/s-1989-27285}} 3. ^Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966) 4. ^{{cite journal | author = Chenjie Zhu | title = Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent | journal = Synthesis | volume = 24| pages = 4235–4241| year = 2010 |last2 = Sun | first2 = Chengguo | last3 = Wei | first3 = Yunyang | doi=10.1055/s-0030-1258281}} 5. ^{{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}} 6. ^{{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}} 7. ^{{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}} 8. ^{{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}} 9. ^{{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 = 20| pages = 3179–3184| year = 2007 |last2 = McDougald | first2 = Graham | last3 = McNab | first3 = Hamish | doi=10.1055/s-2007-990782}} 10. ^Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966) 2 : Furans|Nitriles |
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