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Vinylcyclohexene dioxide

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(Redirected from4-Vinylcyclohexene diepoxide)
Vinylcyclohexene dioxide
Molecular structure of vinylcyclohexene dioxide
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)
AbbreviationsVCD
ECHA InfoCard100.003.126Edit this at Wikidata
UNII
  • C1CC2C(O2)CC1C3CO3
Properties
C8H12O2
Molar mass140.182 g·mol−1
AppearanceColorless liquid[1]
Density1.09 g·cm−3[2][3]
Melting point−108.9 °C (−164.0 °F; 164.2 K)[4]
Boiling point227 °C (441 °F; 500 K)[4]
Vapor pressure13Pa (20 °C)[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

4-Vinylcyclohexene dioxide (VCD) is anorganic compound that contains twoepoxidefunctional groups. It is industrially used as acrosslinking agent for the production of epoxy resins.[5][6] It is a colourless liquid. It is an intermediate for synthesis oforganic compounds.[2]

Preparation and properties

[edit]

4-Vinylcyclohexene dioxide is prepared byepoxidation of4-vinylcyclohexene withperoxybenzoic acid.[5] Its viscosity is 15 mPa·s.[5]

Safety

[edit]

4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as analkylating agent.[5] VCD has toxic effects on fertility. It is a killer ofoocytes, eggs in a female's ovaries, in immatureovarian follicles inmice andrats.[7][8][9]

In pest control, it has been used as an ovotoxic agent for reducing rat fertility.[10]

References

[edit]
  1. ^Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan und Kwok-Yin Wong (2008-09-08). "A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese(II) as the Catalyst".Chemistry: A European Journal.14 (26):7988–7996.doi:10.1002/chem.200800759.PMID 18618538.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^abKh. M. Alimardanov, O. A. Sadygov, N. I. Garibov und M. Ya. Abdullaeva (2012-11-07). "Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide".Russian Journal of Organic Chemistry.48 (10):1302–1308.doi:10.1134/S1070428012100077.S2CID 93780572.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^L. A. Mukhamedova, G. Kh. Gil'manova, M. I. Kudryavtseva, F. G. Nasybullina und A. S. Kireeva (July 1982). "Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane".Pharmaceutical Chemistry Journal.16 (7):510–514.doi:10.1007/BF00761540.S2CID 44566569.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^abcRecord of CAS RN106-87-6 in theGESTIS Substance Database of theInstitute for Occupational Safety and Health, accessed on 24 March 2015.
  5. ^abcdPham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a09_547.pub2.ISBN 3-527-30673-0.
  6. ^US 2555500  "Copolymers of 4-vinylcyclohexene dioxide."
  7. ^Kappeler, Connie J.; Hoyer, Patricia B. (2012-02-01)."4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity".Systems Biology in Reproductive Medicine.58 (1):57–62.doi:10.3109/19396368.2011.648820.ISSN 1939-6376.PMC 3307534.PMID 22239082.
  8. ^Takai, Yasushi; Canning, Jacqueline; Perez, Gloria I.; Pru, James K.; Schlezinger, Jennifer J.; Sherr, David H.; Kolesnick, Richard N.; Yuan, Junying; Flavell, Richard A. (2003-01-01)."Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo".Endocrinology.144 (1):69–74.doi:10.1210/en.2002-220814.ISSN 0013-7227.PMID 12488331.
  9. ^Hoyer, P. B.; Devine, P. J.; Hu, X.; Thompson, K. E.; Sipes, I. G. (2001-02-01). "Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model".Toxicologic Pathology.29 (1):91–99.doi:10.1080/019262301301418892.ISSN 0192-6233.PMID 11215690.S2CID 33667445.
  10. ^Hoyer PB, Devine PJ, Hu X, Thompson KE, Sipes IG (Jan–Feb 2001). "Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model".Toxicol Pathol.29 (1):91–99.doi:10.1080/019262301301418892.PMID 11215690.S2CID 33667445.
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