2-Furonitrile

2-Furonitrile
Names
	Preferred IUPAC name Furan-2-carbonitrile
	Other names 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide
Identifiers
CAS Number	617-90-3;
3D model (JSmol)	Interactive image;
ChemSpider	62458;
ECHA InfoCard	100.009.581
PubChemCID	69245;
UNII	2LRK86H722;
CompTox Dashboard(EPA)	DTXSID40210707;
	InChI InChI=1S/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H Key: YXDXXGXWFJCXEB-UHFFFAOYSA-N; InChI=1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H Key: YXDXXGXWFJCXEB-UHFFFAOYAE;
	SMILES N#Cc1occc1;
Properties
Chemical formula	C5H3NO
Molar mass	93.085g·mol−1
Appearance	colorless (yellow if impure)
Density	1.0650 @20 °C
Boiling point	147°C (297 °F; 420 K)
Hazards
Flash point	35 °C; 95 °F; 308 K
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

2-Furonitrileis a colorless derivative offuranpossessing anitrilegroup.

Synthesis

Industrial synthesis is based on the vapor phaseammoxidationoffurfuralwithammoniaover bismuth molybdate catalyst at 440-480 °C.^[3]

Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural withammoniasalts usinghypervalent iodinereagents^[4]orn-bromosuccinimide.^[5]From furfuralaldoxime(with thionyl chloride-benzotriazole,^[6]triphenylphosphine-iodine reagents,^[7]or heating inDMSO^[8]) and furoic acid amide (flash vacuum pyrolysis).^[9]

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 ofsucrose.^[10]

References

^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)

[1] P. A. Pavlov; Kul'nevich, V. G. (1986). "Synthesis of 5-substituted furannitriles and their reaction with hydrazine".Khimiya Geterotsiklicheskikh Soedinenii.2:181–186.

[2] 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.

[3] Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)

[4] 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.

[5] 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.

[6] 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.

[7] 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.

[8] 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.

[9] 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.

[10] Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)

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