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286-20-4 - Cyclohexene oxide, 98+% - Epoxycyclohexane - 7-Oxabicyclo[4.1.0]heptane - A13185 - Alfa Aesar

A13185 Cyclohexene oxide, 98+%

CAS Number
286-20-4
Synonyms
Epoxycyclohexane
7-Oxabicyclo[4.1.0]heptane

Size Price ($) Quantity Availability
100g 37.89
500g 115.20
2500g 414.40
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Cyclohexene oxide, 98+%

MDL
MFCD00005162
EINECS
206-007-7

Chemical Properties

Formula
C6H10O
Formula Weight
98.15
Melting point
-40°
Boiling Point
129-130°
Flash Point
24°(75°F)
Density
0.972
Refractive Index
1.4520
Solubility
Insoluble in water

Applications

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.

Notes

Store at room temperature. Incompatible with oxidizing agents.

Literature References

Donald. J. Darensbourg .;Jason C. Yarbrough .; Cesar Ortiz.; Cindy C. Fang. Comparative Kinetic Studies of the Copolymerization of Cyclohexene Oxide and Propylene Oxide with Carbon Dioxide in the Presence of Chromium Salen Derivatives. In Situ FTIR Measurements of Copolymer vs Cyclic Carbonate Production.J. Am. Chem. Soc. 2003, 125 (25),7586-7591 .

Stephan Mang.; Andrew I. Cooper.; M. Eamon Colclough.; Naren Chauhan.; Andrew B. Holmes. Copolymerization of CO2 and 1,2-Cyclohexene Oxide Using a CO2-Soluble Chromium Porphyrin Catalyst. Macromolecules. 2000, 33 (2),303-308 .

A general method for the conversion of epoxides to cis-dichloro alkanes, with inversion at both centers, by reaction with triphenylphosphine dichloride, has been exemplified: Org. Synth. Coll., 6, 424 (1988).

Rearrangement to cyclopentanecarboxaldehyde is catalyzed by LiBr on alumina, either by refluxing in toluene or in the gas phase: Synthesis, 394 (1988). An alternative isomerization to the allylic alcohol is induced by base catalysis. Optimized conditions use a mixture of KO-t-Bu and 2.5 equivalents of LDA: Tetrahedron, 46, 2411 (1990). For discussion of the mechanism, see: J. Org. Chem., 61, 820 (1996), and references therein. For a review of the rearrangement of epoxides to allylic alcohols, see: Org. React., 29, 345 (1983).

A general method for the synthesis of ɑ-chloro carbonyl compounds is illustrated by the reaction of cylohexene oxide with the Swern reagent (DMSO/ oxalyl chloride) to give 2-chlorocyclohexanone in 93% yield: Tetrahedron, 51, 2467 (1995).

GHS Hazard and Precautionary Statements

Hazard Statements: H311-H302-H332-H314-H318-H226

Toxic in contact with skin. Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour.

Precautionary Statements: P210-P260-P261-P280-P303+P361+P353-P305+P351+P338-P361-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
383568
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2910.90
TSCA
Yes
RTECS
RN7175000

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