Cyclohexene oxide

Base Information

• Chemical Name: Cyclohexene oxide
• CAS No.: 286-20-4
• Deprecated CAS: 137422-07-2,28165-18-6
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• Hs Code.: H10O MOL WT. 98.14
• European Community (EC) Number: 206-007-7
• NSC Number: 128074,5218
• DSSTox Substance ID: DTXSID6024880
• Nikkaji Number: J2.980G
• Wikipedia: Cyclohexene_oxide
• Wikidata: Q2750068
• ChEMBL ID: CHEMBL1361659
• Mol file: 286-20-4.mol

Synonyms:cyclohexene oxide

Chemical Property of Cyclohexene oxide

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 12mmHg at 25°C
• Melting Point: -40 °C
• Refractive Index: 1.452 - 1.454
• Boiling Point: 130.3 °C at 760 mmHg
• Flash Point: 27.2 °C
• PSA: 12.53000
• Density: 0.97 g/cm³
• LogP: 1.32780
• Storage Temp.: Flammables area
• Water Solubility.: INSOLUBLE
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 70.2

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexene oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-20/21/22-34
• Safety Statements: 26-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxides
• Canonical SMILES: C1CCC2C(C1)O2
• 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. 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.

Technology Process of Cyclohexene oxide

There total 332 articles about Cyclohexene oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

peroxyphenylacetic acid (60538-67-2) + cyclohexene (110-83-8) → phenylacetic acid (103-82-2) + cyclohexane-1,2-epoxide (286-20-4) + benzaldehyde (100-52-7)

Guidance literature:

With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In acetonitrile; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/chem.201202640

Reference yield: 88.0%

peroxyphenylacetic acid (60538-67-2) + cyclohexene (110-83-8) → phenylacetic acid (103-82-2) + cyclohexane-1,2-epoxide (286-20-4) + benzaldehyde (100-52-7) + cyclohexanol (108-93-0)

Guidance literature:

With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In dichloromethane; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/chem.201202640

Reference yield: 86.0%

cyclohexene (110-83-8) → (R)-2-cyclohexen-1-ol (3413-44-3) + (S)-cyclohex-2-en-1-ol (6426-26-2) + cyclohexane-1,2-epoxide (286-20-4)

Guidance literature:

With oxygen; isobutyraldehyde; In acetonitrile; at 25 ℃; for 8h; Reagent/catalyst; enantioselective reaction;

DOI:10.1039/c6nj00808a

upstream raw materials:

4-nitroperbenzoic acid

cyclohexane

methanol

trans-2-hydroxycyclohexyl methanesulfonate

Downstream raw materials:

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol

trans-2-morpholinocyclohexanol

trans-2-(4-methylpiperazin-1-yl)cyclohexanol

cyclopentanealdehyde

Refernces

• 1、 Terent'ev,Boyarinova,Nikishin. "Oxidation of alkenes with hydrogen peroxide, catalyzed by boron trifluoride. Synthesis of vicinal methoxyalkanols". . p. 592 - 596. Retrieved 2008.
• 2、 Ye, Yuan-Jian,Zhou, Xian-Tai,Huang, Jin-Wang,Cai, Jin-Hua,Wu, Wen-Hai,Yu, Han-Cheng,Ji, Hong-Bin,Ji, Liang-Nian. "Styrene-hydroxyethyl methacrylate copolymer microsphere immobilized porphyrinatomanganese(III) as a mild, reusable and highly efficient catalyst for epoxidation of cyclohexene with molecular oxygen". . p. 29 - 34. Retrieved 2010.
• 3、 Ishikawa, Satoshi,Maegawa, Yoshifumi,Waki, Minoru,Inagaki, Shinji. "Well-controlled radical-based epoxidation catalyzed by copper complex immobilized on bipyridine-periodic mesoporous organosilica". . p. 87 - 92. Retrieved 2019.
• 4、 Zhou, Baocheng,Chen, Wenxing. "A mild catalytic oxidation system: FePcOTf/H2O2 applied for cyclohexene dihydroxylation". . p. 8429 - 8439. Retrieved 2015.
• 5、 Kitajima, Nobumasa,Fukui, Hideno,Moro-Oka, Yoshihiko. "A model for methane mono-oxygenase: Dioxygen oxidation of alkanes by use of a μ-oxo binuclear iron complex". . p. 485 - 486. Retrieved 1988.
• 6、 Oldroyd, Richard D.,Sankar, Gopinathan,Thomas, John Meurig,Hunnius, Matthias,Maier, Wilhelm F.. "Creation, characterisation and performance of vanadyl active sites in microporous and mesoporous silica-based catalysts for the selective oxidation of hydrocarbons". . p. 3177 - 3182. Retrieved 1998.
• 7、 Valderruten,Pe?a,Ramírez,Rodríguez-Páez. "Effect of the synthetic method on the catalytic activity of alumina: Epoxidation of cyclohexene". . p. 148 - 154. Retrieved 2015.
• 8、 Arakawa,Ozaki. "-". . p. 1245. Retrieved 1975.
• 9、 Okamoto, Takanobu,Takagi, Shinsuke,Shiragami, Tsutomu,Inoue, Haruo. "Efficient Oxygenation of Alkene through Reductive Quenching of Excited Sb(V)tetraphenylporphyrin by Triphenylphosphine". . p. 687 - 690. Retrieved 1993.
• 10、 Silva, Fernanda P.,Jacinto, Marcos J.,Landers, Richard,Rossi, Liane M.. "Selective allylic oxidation of cyclohexene by a magnetically recoverable cobalt oxide catalyst". . p. 432 - 437. Retrieved 2011.