1,2-Epoxy-4-vinylcyclohexane

Base Information

• Chemical Name: 1,2-Epoxy-4-vinylcyclohexane
• CAS No.: 106-86-5
• Deprecated CAS: 29087-40-9,1629602-29-4
• Molecular Formula: C8H12O
• Molecular Weight: 124.183
• Hs Code.: 29109000
• European Community (EC) Number: 203-436-1
• NSC Number: 35409
• DSSTox Substance ID: DTXSID10861725
• Nikkaji Number: J60.482H
• Mol file: 106-86-5.mol

Synonyms:1,2-epoxy-4-vinylcyclohexane;1,2-VCHE;vinylcyclohexane 1,2-monoepoxide

Chemical Property of 1,2-Epoxy-4-vinylcyclohexane

Chemical Property:

• Appearance/Colour: Transparent Liquid
• Melting Point: -100oC
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 169 °C at 760 mmHg
• Flash Point: 48.1 °C
• PSA: 12.53000
• Density: 1.06 g/cm³
• LogP: 1.73990
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 124.088815002
• Heavy Atom Count: 9
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

1,2-Epoxy-4-vinylcyclohexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• Statements: 45-10-20/21/22-40-36-22
• Safety Statements: 53-16-23-36/37/39-45-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1CCC2C(C1)O2
• Recent ClinicalTrials: Study to Investigate the Dose Response, Safety and Efficacy of Nebulized EP-101(SUN101) in Patients With Chronic Obstructive Pulmonary Disease (COPD): GOLDEN-1 Study
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo-Controlled, Multi-Center, Seven Arm, Four-Period Cross-over, Incomplete Block Design, 7-Day Dosing Study to Assess the Dose-Response, Safety, and Efficacy of EP-101 in Subjects with Moderate to Severe COPD
• Uses: Vinylcyclohexene monoxide is a chemical intermediate; it can be copolymerized with other epoxides to yield polyglycols having unsaturation available for further reaction.

Technology Process of 1,2-Epoxy-4-vinylcyclohexane

There total 16 articles about 1,2-Epoxy-4-vinylcyclohexane 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: 99.0%

4-ethenylcyclohexene (100-40-3) → 1,2-Epoxy-4-vinylcyclohexane (106-86-5)

Guidance literature:

With [(C₁₈H₃₇)₂(CH₃)₂N]₃[SiO₄H(WO₅)₃]; dihydrogen peroxide; In ethyl acetate; at 59.84 ℃; for 2h; Green chemistry;

DOI:10.1039/c4ra04036h

Reference yield: 40.0%

4-ethenylcyclohexene (100-40-3) → 1,2-Epoxy-4-vinylcyclohexane (106-86-5) + 3,4-dihydroxy-1-vinylcyclohexane (31646-64-7)

Guidance literature:

With dihydrogen peroxide; magnesium sulfate; methyltrioxorhenium(VII); In tert-butyl alcohol; at 15 ℃; for 2h;

Reference yield: 2.5%

1,1,3,3-tetrachloropropanone (632-21-3) + 4-ethenylcyclohexene (100-40-3) → 4-vinylcyclohexene dioxide (106-87-6,73752-15-5) + 1,2-Epoxy-4-vinylcyclohexane (106-86-5) + 7,8-Epoxy-1-Cyclohexene (5116-65-4) + tetrachloroacetone hydrate (78950-58-0)

Guidance literature:

With disodium hydrogenphosphate; dihydrogen peroxide; In chloroform; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(01)93284-8

upstream raw materials:

peracetic acid

4-ethenylcyclohexene

1,1,3,3-tetrachloropropanone

acetic acid

Downstream raw materials:

3,4-dihydroxy-1-vinylcyclohexane

4-azido-3-hydroxy-1-vinylcyclohexane

3-azido-4-hydroxy-1-vinylcyclohexane

3-amino-4-hydroxy-1-vinylcyclohexane

Refernces

• 1、 Liu, Hai-Yang,Yam, Fei,Xie, Yu-Tao,Li, Xiao-Yuan,Chang, Chi K.. "A bulky bis-pocket manganese(V)-oxo corrole complex: Observation of oxygen atom transfer between triply bonded MnV≡O and alkene". . p. 12890 - 12891. Retrieved 2009.
• 2、 Gomes, Ana C.,Neves, Patrícia,Figueiredo, Sónia,Fernandes, José A.,Valente, Anabela A.,Almeida Paz, Filipe A.,Pillinger, Martyn,Lopes, André D.,Gon?alves, Isabel S.. "Tris(pyrazolyl)methane molybdenum tricarbonyl complexes as catalyst precursors for olefin epoxidation". . p. 64 - 76. Retrieved 2013.
• 3、 Carlson et al.. "-". . p. 3832. Retrieved 1971.
• 4、 Ferrer, íngrid,Fontrodona, Xavier,Roig, Anna,Rodríguez, Montserrat,Romero, Isabel. "A Recoverable Ruthenium Aqua Complex Supported on Silica Particles: An Efficient Epoxidation Catalyst". . p. 4096 - 4107. Retrieved 2017.
• 5、 Stark, Charles J.. "EPOXIDATION OF OLEFINS BY HYDROGEN PEROXIDE IN THE PRESENCE OF TETRACHLOROACETONE". . p. 2089 - 2092. Retrieved 1981.
• 6、 Kesavan, Venkitasamy,Chandrasekaran, Srinivasan. "Stereospecific and regioselective catalytic epoxidation of alkenes by a novel ruthenium(II) complex under aerobic conditions". . p. 3115 - 3116. Retrieved 1997.
• 7、 Juwiler, David,Blum, Jochanan,Neumann, Ronny. "Metal silicates by a molecular route as catalysts for epoxidation of alkenes with tert-butyl hydroperoxide". . p. 1123 - 1124. Retrieved 1998.
• 8、 Dakkach, Mohamed,Lopez, M. Isabel,Romero, Isabel,Rodriguez, Montserrat,Atlamsani, Ahmed,Parella, Teodor,Fontrodona, Xavier,Llobet, Antoni. "New Ru(II) complexes with anionic and neutral N-donor ligands as epoxidation catalysts: An evaluation of geometrical and electronic effects". . p. 7072 - 7079. Retrieved 2010.
• 9、 Dakkach, Mohamed,Fontrodona, Xavier,Parella, Teodor,Atlamsani, Ahmed,Romero, Isabel,Rodriguez, Montserrat. "Polypyrrole-functionalized ruthenium carbene catalysts as efficient heterogeneous systems for olefin epoxidation". . p. 9916 - 9923. Retrieved 2014.
• 10、 Jiang, Wenchan,Gorden, John D.,Goldsmith, Christian R.. "Catalysis of alkene epoxidation by a series of gallium(III) complexes with neutral N-donor ligands". . p. 5814 - 5823. Retrieved 2013.