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Cyclohexenone

Cyclohexenone^[1]

IUPAC name	1-Cyclohex-2-enone
Identifiers
CAS number	930-68-7
PubChem	13594
SMILES	C1CC=CC(=O)C1
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

Additional recommended knowledge

What is the Sensitivity of my Balance?

Essential Laboratory Skills Guide

Recognize and detect the effects of electrostatic charges on your balance

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

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