2-Cyclohexen-1-one

Description

2-Cyclohexen-1-one is a ketone, or more precisely an enone. It is colorless liquid, but commercial samples are often yellow. Industrially, cyclohexenone is prepared from phenol by Birch reduction. Common reactions include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.

Chemical properties

CLEAR LIGHT YELLOW TO YELLOW LIQUID

The Uses of 2-Cyclohexen-1-one

2-Cyclohexen-1-one is used as intermediates.

Definition

ChEBI: A cyclohexenone having its C2C double bond at the 2-position.

What are the applications of Application

2-Cyclohexen-1-one can be used to versatile electrophile employed in a range of addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with enol silanes, and phosphoniosilylations.

Reactions

2-Cyclohexen-1-one  was employed in a Baylis–Hillman-type reaction with formaldehyde, and the newly formed primary alcohol was protected as silyl ether.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 31, p. 4209, 1983 DOI: 10.1248/cpb.31.4209
Journal of the American Chemical Society, 110, p. 6591, 1988 DOI: 10.1021/ja00227a065

Contact allergens

This strong sensitizer has been responsible for chemical burning followed by sensitization in a chemistry student.

Safety Profile

A poison by ingestion, inhalation, intraperitoneal, and skin contact routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritant fumes. See also KETONES.

Solubility in organics

Acetone, Alcohol, Benzene