Furfural

Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from dryed biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.

Furfural
Names
Preferred IUPAC name
Furan-2-carbaldehyde
Other names
Furfural, furan-2-carboxaldehyde, fural, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.389
KEGG
PubChem CID
UNII
  • InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H Y
    Key: HYBBIBNJHNGZAN-UHFFFAOYSA-N Y
  • InChI=1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
    Key: HYBBIBNJHNGZAN-UHFFFAOYAD
SMILES
  • c1cc(oc1)C=O
Properties
C5H4O2
Molar mass 96.085 g·mol−1
Appearance Colorless oil
Odor Almond-like
Density 1.1601 g/mL (20 °C)
Melting point −37 °C (−35 °F; 236 K)
Boiling point 162 °C (324 °F; 435 K)
83 g/L
Vapor pressure 2 mmHg (20 °C)
Magnetic susceptibility (χ)
−47.1×10−6 cm3/mol
Hazards
Flash point 62 °C (144 °F; 335 K)
Explosive limits 2.1–19.3%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
300–500 mg/kg (oral, mice)
LC50 (median concentration)
  • 370 ppm (dog, 6 hr)
  • 175 ppm (rat, 6 hr)
  • 1037 ppm (rat, 1 hr)
LCLo (lowest published)
  • 370 ppm (mouse, 6 hr)
  • 260 ppm (rat)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (20 mg/m3) [skin]
REL (Recommended)
No established REL
IDLH (Immediate danger)
100 ppm
Related compounds
Related Furan-2-carbaldehydes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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