Vinylcyclohexene dioxide
Chemical compound
From Wikipedia, the free encyclopedia
4-Vinylcyclohexene dioxide (VCD) is an organic compound that contains two epoxide functional groups. It is industrially used as a crosslinking agent for the production of epoxy resins.[5][6] It is a colourless liquid. It is an intermediate for synthesis of organic compounds.[2]
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| Names | |
|---|---|
| IUPAC name
3-Oxiranyl-7-oxabicyclo[4.1.0]heptane | |
| Other names
1,2-Epoxy-4-(epoxyethyl)cyclohexane 4-Vinylcyclohexene diepoxide | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | VCD |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.126 |
| EC Number |
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| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 2810 (1-VINYL-3-CYCLOHEXENE DIOXIDE) |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H12O2 | |
| Molar mass | 140.182 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Density | 1.09 g·cm−3[2][3] |
| Melting point | −108.9 °C (−164.0 °F; 164.2 K)[4] |
| Boiling point | 227 °C (441 °F; 500 K)[4] |
| Vapor pressure | 13 Pa (20 °C)[4] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Toxic |
| GHS labelling: | |
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| Danger | |
| H302, H331, H341, H350, H360F | |
| P203, P261, P264, P270, P271, P280, P301+P317, P304+P340, P316, P318, P321, P330, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and properties
4-Vinylcyclohexene dioxide is prepared by epoxidation of 4-vinylcyclohexene with peroxybenzoic acid.[5] Its viscosity is 15 mPa·s.[5]
Safety
4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an alkylating agent.[5] VCD has toxic effects on fertility. It is a killer of oocytes, eggs in a female's ovaries, in immature ovarian follicles in mice and rats.[7][8][9]
In pest control, it has been used as an ovotoxic agent for reducing rat fertility.[10]