2-Furonitrile

2-Furonitrile

File:2-Furonitrile.svg
Names
Preferred IUPAC name Furan-2-carbonitrile
Other names 2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide
Identifiers
CAS Number	617-90-3 checkY
3D model (JSmol)	Interactive image
ChemSpider	62458 checkY
ECHA InfoCard
E number
PubChem CID	69245
UNII	2LRK86H722 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H checkY Key: YXDXXGXWFJCXEB-UHFFFAOYSA-N checkY 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
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 their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

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.

Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with ammonia salts using hypervalent iodine reagents or n-bromosuccinimide. From furfural aldoxime (with thionyl chloride-benzotriazole, triphenylphosphine-iodine reagents, or heating in DMSO) and furoic acid amide (flash vacuum pyrolysis).

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.