Cyclohexenone

Cyclohexenone[1]
Identifiers
CAS number 930-68-7 Y
PubChem 13594
ChemSpider 13005 Y
KEGG C02395 Y
ChEBI CHEBI:15977 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H8O
Molar mass 96.12712
Appearance Clear colorless liquid
Density 0.993 g/mL
Melting point

−53 °C

Boiling point

171–173 °C

Hazards
NFPA 704
3
1
0
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.[2] It is a clear colorless liquid with a boiling point of 171–173 °C.

Industrially, cyclohexenone is prepared from phenol by Birch reduction.[3]

Common reactions involving cyclohexenone include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.[4][5]

References

  1. ^ Cyclohexenone at Sigma-Aldrich
  2. ^ Podraze, K.F. Org. Prep. Proced. Int., 1991, 23, p. 217.
  3. ^ Organic Building Blocks of the Chemical Industry, Harry H. Szmant, ISBN 978-0471855453
  4. ^ Michael G. Organ and Paul Anderson (1996). "Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent Selectivity". Journal of Chemical Education 73 (12): 1193. doi:10.1021/ed073p1193. 
  5. ^ Tet. Lett. 34, 3881, (1993)