Cyclohexenone

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 colorless liquid, but commercial samples are often yellow.

Cyclohexenone
Names
Preferred IUPAC name
Cyclohex-2-en-1-one
Other names
1-Cyclohex-2-enone
Identifiers
3D model (JSmol)
3DMet
1280477
ChEBI
ChemSpider
ECHA InfoCard 100.012.021
EC Number
  • 213-223-5
2792
KEGG
UNII
  • InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 Y
    Key: FWFSEYBSWVRWGL-UHFFFAOYSA-N Y
  • InChI=1/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2
    Key: FWFSEYBSWVRWGL-UHFFFAOYAT
  • C1CC=CC(=O)C1
Properties
C6H8O
Molar mass 96.129 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 °C)
Hazards
GHS labelling:
Danger
H226, H301, H310, H319, H330, H331
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P320, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
1
3
0
Lethal dose or concentration (LD, LC):
220 mg kg−1 (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

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