Cyclohexenone

Cyclohexenone
Skeletal formula of cyclohexenone
Ball-and-stick model of the cyclohexenone molecule
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 Edit this at Wikidata
EC Number
  • 213-223-5
2792
KEGG
UNII
  • InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 checkY
    Key: FWFSEYBSWVRWGL-UHFFFAOYSA-N checkY
  • 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 [1]
Melting point −53 °C (−63 °F; 220 K)[1]
Boiling point 171 to 173 °C (340 to 343 °F; 444 to 446 K)[1]
41.3 g/L (25 °C)
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)

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 colorless liquid, but commercial samples are often yellow.

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

Cyclohexenone is a ketone, or more precisely an enone. Common reactions include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.[4][5]

  1. ^ a b c 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 978-0-471-85545-3
  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. ^ Tetrahedron Lett. 34, 3881, (1993)