Cyclohexene oxide Property

Melting point:

-40 °C

Boiling point:

129-130 °C(lit.)

Density 

0.97 g/mL at 25 °C(lit.)

vapor pressure 

12 hPa (20 °C)

refractive index 

n20/D 1.452(lit.)

Flash point:

81 °F

storage temp. 

Store below +30°C.

form 

Liquid

color 

Clear colorless to yellow

explosive limit

1.2-6.5%(V)

Water Solubility 

INSOLUBLE

BRN 

383568

CAS DataBase Reference

286-20-4(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexene oxide(286-20-4)

EPA Substance Registry System

Cyclohexene oxide (286-20-4)

Safety

Hazard Codes 

C

Risk Statements 

10-20/21/22-34

Safety Statements 

26-36/37/39-45-16

RIDADR 

UN 2924 3/PG 3

WGK Germany 

1

RTECS 

RN7175000

Autoignition Temperature

703 °F

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29109000

Hazardous Substances Data

286-20-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 1060 mg/kg LD50 dermal Rabbit 612 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Cyclohexene oxide Chemical Properties,Usage,Production

Chemical Properties

clear colorless to yellow liquid

Uses

Cyclohexene oxide has been patented for use as an insecticidal fumigant.
Cyclohexene oxide is an important intermediate in the organic industry. It is employed in the manufacture of medicines, pesticides, dyes, and perfumes. In addition, cyclohexene oxide can be used as a monomer in polymerization, chain-cutting agent, flame retardant and diluting agent among other uses.
Cyclohexene oxide is useful as a monomer in polymerization with CO2 for production of cyclic carbonates and polycarbonates in the presence of different catalysts.

Uses

It is an important raw material and intermediate used in organic synthesis, dyestuffs and in agrochemical industries. It is used in medicine. Cyclohexene oxide (epoxycyclohexane) is an useful monomer in polymerization and coating industry. It is used in the synthesis of alicyclic target materials including pharmaceuticals, perfumery and dyestuffs. It is used as a monomer in photopolymerizations, with carbonmonoxide to yield aromatic polycarbonates which has minimum impurities.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1251, 1973 DOI: 10.1021/jo00946a053
Tetrahedron Letters, 29, p. 2967, 1988 DOI: 10.1016/0040-4039(88)85059-7

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by ingestion, skin contact, intraperitoneal, and intramuscular routes. Mildly toxic by inhalation. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A flammable liquid and dangerous fire hazard when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritant fumes.

Purification Methods

Fractionate the oxide through an efficient column. The main impurity is probably H2O. Dry it over MgSO4, filter and distil it several times (b 129-134o/760mm). The residue is sometimes hard to remove from the distilling flask. To avoid this difficulty, add a small amount of a mixture of ground NaCl and Celite (1:1) to help break up the residue particularly if H2O is added. [Osterberg Org Synth Coll Vol I 185 1948, Beilstein 17 H 21, 17/1 V 203.]