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-(pipoeridin-1-yl)cyclohexanol

trans-2-morpholinocyclohexanol

optically inactive 1,4-bis-(trans-2-hydroxy-cyclohexyl)-piperazine

Refernces

Epoxidation of cyclohexene with O₂ over the composite catalysts of Mn-montmorillonite coordinated with novel Schiff-base ligands

10.1039/c3ra42749h

The research focuses on the development and characterization of heterogeneous catalysts composed of Mn-montmorillonite coordinated with novel Schiff-base ligands for the epoxidation of cyclohexene using molecular oxygen under Mukaiyama conditions. The catalysts were synthesized and characterized using various analytical techniques including IR, UV-vis DRS, XRD, SEM, and ICP. The study optimized reaction conditions to achieve high conversion rates and selectivity for the production of epoxycyclohexane, with the best results showing 100% conversion and 90.0% selectivity at 40°C in 5 hours using molecular oxygen as the oxidant in acetonitrile. The catalysts demonstrated stability over at least three cycles, indicating their potential as environmentally friendly and economical options for industrial epoxidation processes. The reactants involved in the catalytic epoxidation reaction included cyclohexene, isobutylaldehyde, and the Mn-montmorillonite composite catalysts. The analysis of the reaction involved the use of GC-MS and GC equipped with specific columns to determine the conversion and selectivity of the epoxide product.

TiCl₄ and Grignard reagent-promoted ring-opening reactions of various epoxides: synthesis of γ-hydroxy-α,α-difluoromethylenephosphonates

10.1016/j.tetlet.2008.07.146

The study investigates the synthesis of diethyl c-hydroxy-a,a-difluoromethylenephosphonates through the ring-opening reactions of epoxides. Key chemicals involved include titanium tetrachloride (TiCl4), which acts as a Lewis acid to promote the ring-opening of epoxides, and lithium diethyl difluoromethylenephosphonate, which serves as a nucleophile. The study explores the reactivity of various epoxides, such as propylene oxide, 1,2-butene oxide, styrene oxide, and cyclohexene oxide, with these reagents. The reactions are regioselective, favoring attack at the less hindered site of the epoxide ring. The study also examines the use of Grignard reagents, which act as both nucleophiles and Lewis acids, leading to the formation of halohydrins. The synthesized compounds have potential applications in the design of non-hydrolyzable analogues of biologically active phosphate esters and as substrates for certain enzymes.