Cyclohexene oxide

Cyclohexene oxide
  • CAS No.:286-20-4
Other grades of this product :
Cyclohexene oxide Basic information
Product Name:Cyclohexene oxide
Synonyms:1,2-epoxy-cyclohexan;2,3-tetramethyleneoxirane;7-oxabicyclo(3.1.0)heptane;Bicyclo[4.1.0]heptane, 7-oxa-;Ccho;cis-1,2-epoxycyclohexane;Cyclohexane, 1,2-epoxy-;cyclohexane,1,2-epoxy-
CAS:286-20-4
MF:C6H10O
MW:98.14
EINECS:206-007-7
Product Categories:Alcohol& Phenol& Ethers;Pharmaceutical Intermediates
Mol File:286-20-4.mol
Cyclohexene oxide Chemical Properties
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.)
Fp 81 °F
storage temp. Store below +30°C.
form Liquid
color Clear colorless to yellow
explosive limit1.2-6.5%(V)
Water Solubility INSOLUBLE
BRN 383568
CAS DataBase Reference286-20-4(CAS DataBase Reference)
NIST Chemistry ReferenceCyclohexene oxide(286-20-4)
EPA Substance Registry SystemCyclohexene oxide (286-20-4)
Safety Information
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 Temperature703 °F
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29109000
Hazardous Substances Data286-20-4(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1060 mg/kg LD50 dermal Rabbit 612 mg/kg
MSDS Information
ProviderLanguage
1,2-Epoxycyclohexane English
SigmaAldrich English
ACROS English
ALFA English
Cyclohexene oxide Usage And Synthesis
Chemical Propertiesclear colorless to yellow liquid
UsesCyclohexene 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.
UsesIt 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/jo00946a053Tetrahedron Letters, 29, p. 2967, 1988 DOI: 10.1016/0040-4039(88)85059-7
Flammability and ExplosibilityFlammable
Safety ProfileModerately 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 MethodsFractionate 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.]

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