2-Furonitrile

2-Furonitrile is a colorless derivative of furan possessing a nitrile group.

2-Furonitrile

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

Synthesis

Industrial 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]

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.^[10]