2-Furonitrile

Source: Wikipedia, the free encyclopedia.
2-Furonitrile
Names
Preferred IUPAC name
Furan-2-carbonitrile
Other names
2-Cyanofuran; 2-Furancarbonitrile; 2-Furyl cyanide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.009.581 Edit this at Wikidata
UNII
  • 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
  • N#Cc1occc1
Properties
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).
checkY verify (what is checkY☒N ?)

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.[3]

Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with

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]

References

  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. S2CID 97316774
    .
  3. ^ Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
  4. doi:10.1055/s-0030-1258281
    .
  5. S2CID 98593006
    .
  6. doi:10.1080/00397919908086161
    .
  7. doi:10.1080/00397910500333225
    .
  8. ISSN 0040-4039
    .
  9. doi:10.1055/s-2007-990782
    .
  10. ^ Thomas J. Jennings, "Process for preparing furonitrile", US Patent 3,260,731 (1966)
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