2,3-Dihydrofuran
Chemical compound
From Wikipedia, the free encyclopedia
2,3-Dihydrofuran is a heterocyclic compound with the formula C4H6O. It is isomeric with 2,5-dihydrofuran. 2,3-Dihydrofuran is one of the simplest enol ethers. It is a colorless volatile liquid.
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| Preferred IUPAC name
2,3-Dihydrofuran | |||
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3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.013.407 | ||
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C4H6O | |||
| Molar mass | 70.091 g·mol−1 | ||
| Density | 0,927 g/mL | ||
| Boiling point | 54.6 °C (130.3 °F; 327.8 K)[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions
It undergoes lithiation upon treatment with butyl lithium. The resulting 2-lithio derivative is a versatile intermediate.[2][3]
Synthesis and occurrence
2,3-Dihydrofurans are intermediates in the Feist–Benary synthesis of furans from α-halogen ketones and β-dicarbonyl compounds.[4]
The 2,3-dihydrofuran ring can be synthesized by several methods. These routes usually involve cyclization or cycloaddition reactions of carbonyl compounds using metal-containing catalysts.[5][6] Iodine can also serve as a catalyst[7] as well as Raney nickel.[8]