4-Vinylcyclohexene dioxide

Base Information

• Chemical Name: 4-Vinylcyclohexene dioxide
• CAS No.: 106-87-6
• Deprecated CAS: 25550-49-6,60304-41-8,119418-67-6,61489-53-0,37205-95-1,112721-27-4,73752-15-5,144046-23-1,39283-09-5,39465-56-0
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Hs Code.: 2932999099
• European Community (EC) Number: 203-437-7
• ICSC Number: 0820
• NSC Number: 61281,54752,7583
• UN Number: 2810
• UNII: 596C064IG4
• DSSTox Substance ID: DTXSID0020604
• Nikkaji Number: J65.676C
• Wikipedia: Vinylcyclohexene_dioxide
• Wikidata: Q2618250
• NCI Thesaurus Code: C44326
• Metabolomics Workbench ID: 60336
• ChEMBL ID: CHEMBL1734307
• Mol file: 106-87-6.mol

Synonyms:1-epoxyethyl-3,4-epoxycyclohexane;4-vinyl-1-cyclohexene dioxide;4-vinylcyclohexene diepoxide;vinyl cyclohexane diepoxide;vinyl cyclohexene diepoxide;vinylcyclohexene diepoxide

Chemical Property of 4-Vinylcyclohexene dioxide

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.119mmHg at 25°C
• Melting Point: -55°C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 226.999 °C at 760 mmHg
• Flash Point: 86.412 °C
• PSA: 25.06000
• Density: 1.228 g/cm³
• LogP: 0.95270
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: 154.7g/L(20 oC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 157
• Transport DOT Label: Poison

Purity/Quality:

99% Min. ^*data from raw suppliers

Vinylcyclohexene dioxide 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-68/20/21/22-68
• Safety Statements: 23-24-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxides
• Canonical SMILES: C1CC2C(O2)CC1C3CO3
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. Inhalation may cause lung oedema. Exposure at high levels could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the kidneys, ovary and testes. This may result in tissue lesions. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Uses: Vinylcyclohexene dioxide (VCD) is used to study toxicity as an ovotoxin,and it's also used to understand its mechanisms of toxicity towards ovarian follicles and effects on epithelial differentiation. As a chemical intermediate and as a reactive diluent for diepoxides and epoxy resins. Vinylcyclohexene dioxide (VCD) may be used to study and understand its effect on ovarian follicles and effects on epithelial differentiation.

Technology Process of 4-Vinylcyclohexene dioxide

There total 7 articles about 4-Vinylcyclohexene dioxide 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: 88.0%

4-ethenylcyclohexene (100-40-3) → 4-vinylcyclohexene dioxide (106-87-6,73752-15-5)

Guidance literature:

With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide; In acetonitrile; tert-butyl alcohol; at 20 ℃; for 1h; Green chemistry;

DOI:10.1021/jo5003938

Reference yield: 74.0%

4-ethenylcyclohexene (100-40-3) → 4-vinylcyclohexene dioxide (106-87-6,73752-15-5) + C8H12O

Guidance literature:

With C₂₀H₂₆FeN₄⁽²⁺⁾*2CF₃O₃S^(1-); dihydrogen peroxide; acetic acid; In acetonitrile; at 0 ℃; for 0.166667h; regioselective reaction;

DOI:10.1002/ejic.201500213

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:

4-ethenylcyclohexene

1,1,3,3-tetrachloropropanone

methanol

Downstream raw materials:

4-(1,2-dihydroxyethyl)cyclohexane-1,2-diol

3,4-epoxyacetylcyclohexane

3-acetylcyclohexanone

4-(1-oxoethyl)-1-cyclohexanone

Refernces

• 1、 Dubois, Geraud,Murphy, Andrew,Daniel,Stack. "Simple iron catalyst for terminal alkene epoxidation". . p. 2469 - 2472. Retrieved 2003.
• 2、 Ai, Chengmei,Zhu, Fuyuan,Wang, Yanmei,Yan, Zhaohua,Lin, Sen. "SO2F2-Mediated Epoxidation of Olefins with Hydrogen Peroxide". . p. 11928 - 11934. Retrieved 2019/10/02.
• 3、 Spannring, Peter,Yazerski, Vital A.,Chen, Jianming,Otte, Matthias,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.,Klein Gebbink, Robertus J. M.. "Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4". . p. 3462 - 3466. Retrieved 2015/08/06.