| Furan | |
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Furan |
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Other names
Oxole, furfuran, furane (misspelling),[1] divinylene oxide, |
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| Identifiers | |
| CAS number | 110-00-9 |
| PubChem | 8029 |
| ChemSpider | 7738 |
| KEGG | C14275 |
| ChEBI | CHEBI:35559 |
| ChEMBL | CHEMBL278980 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H4O |
| Molar mass | 68.07 g/mol |
| Appearance | colorless, volatile liquid |
| Density | 0.936 g/mL |
| Melting point |
−85.6 °C |
| Boiling point |
31.3 °C |
| Hazards | |
| Flash point | −69 °C |
| Related compounds | |
| Related heterocycles | Pyrrole Thiophene |
| Related compounds | Tetrahydrofuran (THF) 2,5-Dimethylfuran Benzofuran Dibenzofuran |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals.[2]
Contents |
The name furan comes from the Latin furfur, which means bran.[3] 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.[4][5]
Industrially, furan is manufactured by the palladium-catalyzed decarbonylation of furfural, or by the copper-catalyzed oxidation of 1,3-butadiene:[2]
In the laboratory, furan can be obtained from furfural by oxidation to furan-2-carboxylic acid, followed by decarboxylation.[6] It can also be prepared directly by thermal decomposition of pentose-containing materials, cellulosic solids especially pine-wood.
The Feist-Benary synthesis is a classic way to synthesize furans, although many syntheses have been developed.[7] One of the simplest synthesis methods for furans is the reaction of 1,4-diketones with phosphorus pentoxide (P2O5) in the Paal-Knorr Synthesis. The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone-mediated cyclization of 1,3-diketones[8]
Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system (see Hückel's rule) similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.
Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran.