Cyclohexenone

Cyclohexenone
Names
	Preferred IUPAC name Cyclohex-2-en-1-one
	Other names 1-Cyclohex-2-enone
Identifiers
CAS Number	930-68-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1280477
ChEBI	CHEBI:15977 ;
ChemSpider	13005 ;
ECHA InfoCard	100.012.021
EC Number	213-223-5;
Gmelin Reference	2792
KEGG	C02395 ;
PubChem CID	13594;
UNII	445160R1U6 ;
CompTox Dashboard (EPA)	DTXSID1024881 ;
	InChI InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 Key: FWFSEYBSWVRWGL-UHFFFAOYSA-N ; InChI=1/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 Key: FWFSEYBSWVRWGL-UHFFFAOYAT;
	SMILES C1CC=CC(=O)C1;
Properties
Chemical formula	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)
Solubility in water	41.3 g/L (25 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H310, H319, H330, H331
Precautionary statements	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):
LD50 (median dose)	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). verify (what is ?) 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 colorless liquid, but commercial samples are often yellow.

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.