2-Cyclohexen-1-one Chemical Properties

Melting point:

-53 °C

Boiling point:

171-173 °C(lit.)

Density 

0.993 g/mL at 25 °C(lit.)

vapor pressure 

760 mm Hg ( 168 °C)

FEMA 

4517 | 2-CYCLOHEXENONE

refractive index 

n20/D 1.488(lit.)

Flash point:

133 °F

storage temp. 

0-6°C

solubility 

soluble in Chloroform, Methanol

form 

Liquid

color 

Clear light yellow to yellow

Odor

No strong odour known

Odor Type

roasted

Water Solubility 

SOLUBLE

JECFA Number

2052

BRN 

1280477

LogP

0.61

CAS DataBase Reference

930-68-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Cyclohexen-1-one(930-68-7)

EPA Substance Registry System

2-Cyclohexen-1-one (930-68-7)

Safety Information

Hazard Codes 

T

Risk Statements 

22-23/24-36

Safety Statements 

23-36/37/39-45-27-26-20-9

RIDADR 

UN 2929 6.1/PG 2

WGK Germany 

3

RTECS 

GW7000000

Hazard Note 

Toxic

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29142990

MSDS

• Language:English Provider:2-Cyclohexen-1-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Cyclohexen-1-one Usage And Synthesis

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

Uses

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

Definition

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

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

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