Cyclohexenone
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| Names | |||
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Preferred IUPAC name
Cyclohex-2-en-1-one
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| Other names
1-Cyclohex-2-enone
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| Identifiers | |||
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3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.012.021 | ||
| KEGG | |||
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PubChem CID
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| Properties | |||
| C6H8O | |||
| Molar mass | 96.13 g·mol−1 | ||
| Appearance | Clear colorless liquid | ||
| Density | 0.993 g/mL | ||
| Melting point | −53 °C (−63 °F; 220 K) | ||
| Boiling point | 171 to 173 °C (340 to 343 °F; 444 to 446 K) | ||
| 41.3 g/L (25 ℃) | |||
| Hazards | |||
| R-phrases (outdated) | R10, R22, R23/24, R36/37/38 | ||
| S-phrases (outdated) | S20, S27, S36/37/39, S45, S60 | ||
| NFPA 704 | |||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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220 mg kg−1 (rat, oral) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Cyclohexenone is an organic compound which is a versatile intermediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. It is clear colorless liquid in pure state but a commercially available product is mostly yellowish liquid.
Industrially, cyclohexenone is prepared from phenol by Birch reduction.
Cyclohexenone is a ketone, or more precisely an enone. Common reactions include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.
It is soluble in many solvents, such as alcohols, ethers, haloalkanes, esters, and also is miscible with polar aprotic solvents.
Cyclohexenone reacts both ketones and alkenes. It has an electron-poor carbon-carbon double bond as a typical representative of the α, β-unsaturated carbonyl compounds.
With strong bases, the positions 4 and 6 (the two CH2-groups of the carbonyl group and the C-C double bond adjacent) are deprotonated.
There are several different synthetic routes for the production of cyclohexenone. The reduction following acid hydrolysis of 3-ethoxy-2-cyclohexen-1-one is available for the laboratory scale. The precursor is accessible from resorcinol via 1,3-cyclohexanedione.
Anisole is also available. Cyclohexanone is obtained by Birch reduction followed by acid hydrolysis.
It can be obtained from cyclohexanone by α-bromination and elimination, or from 3-chloro cyclohexene by means of hydrolysis and oxidation.
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