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Furans

Furan
Full structural formula of furan
Skeletal formula showing numbering convention
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
Furan
Systematic IUPAC name
Oxole
5-Oxacyclopenta-1,3-diene
5-Oxacyclo-1,3-pentadiene
1,4-Epoxybuta-1,3-diene
1,4-Epoxy-1,3-butadiene
Other names
Furfuran
Furane (misspelling)
Divinylene oxide
Identifiers
110-00-9 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:35559 YesY
ChEMBL ChEMBL278980 YesY
ChemSpider 7738 YesY
ECHA InfoCard 100.003.390
KEGG C14275 YesY
PubChem 8029
Properties
C4H4O
Molar mass 68.08 g·mol−1
Appearance Colorless, volatile liquid
Density 0.936 g/mL
Melting point −85.6 °C (−122.1 °F; 187.6 K)
Boiling point 31.3 °C (88.3 °F; 304.4 K)
-43.09·10−6 cm3/mol
Hazards
Safety data sheet Pennakem
R-phrases R26/27/28, R45
S-phrases S16, S37, S45, S28
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −69 °C (−92 °F; 204 K)
390 °C (734 °F; 663 K)
Explosive limits Lower: 2.3%
Upper: 14.3% at 20 °C
Lethal dose or concentration (LD, LC):
LD50 (median dose)
> 2 g/kg (rat)
Related compounds
Related heterocycles
Pyrrole
Thiophene
Related compounds
Tetrahydrofuran (THF)
2,5-Dimethylfuran
Benzofuran
Dibenzofuran
Structure
C2v
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans.

Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. It is toxic and may be carcinogenic in humans. Furan is used as a starting point to other specialty chemicals.

The name "furan" comes from the Latin furfur, which means bran. The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it "tetraphenol" (as if it were a four-carbon analog to phenol, C6H6O).

Industrially, furan is manufactured by the palladium-catalyzed decarbonylation of furfural, or by the copper-catalyzed oxidation of 1,3-butadiene:


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Wikipedia

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