Vinylcyclohexene dioxide

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
CAS Number	106-87-6 ;
3D model (JSmol)	Interactive image;
Abbreviations	VCD
ChEBI	CHEBI:59001;
ChEMBL	ChEMBL1734307;
ChemSpider	7545;
ECHA InfoCard	100.003.126
EC Number	203-437-7;
KEGG	C19311;
PubChem CID	7833;
RTECS number	RN8640000;
UNII	596C064IG4 ;
UN number	2810 (1-VINYL-3-CYCLOHEXENE DIOXIDE)
CompTox Dashboard (EPA)	DTXSID0020604 ;
	InChI InChI=1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2 Key: OECTYKWYRCHAKR-UHFFFAOYSA-N;
	SMILES C1CC2C(O2)CC1C3CO3;
Properties
Chemical formula	C8H12O2
Molar mass	140.182 g·mol−1
Appearance	Colorless liquid
Density	1.09 g·cm−3
Melting point	−108.9 °C (−164.0 °F; 164.2 K)
Boiling point	227 °C (441 °F; 500 K)
Vapor pressure	13 Pa (20 °C)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H331, H341, H350, H360F
Precautionary statements	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). Infobox references

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]

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]

References

↑ 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. Bibcode:2008ChEuJ..14.7988H. doi:10.1002/chem.200800759. PMID 18618538.{{cite journal}}: CS1 maint: multiple names: authors list (link)
1 2 Kh. 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)
↑ 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)
1 2 3 Record of CAS RN 106-87-6 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 24 March 2015.
1 2 3 4 Pham, 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.
↑ US 2555500 "Copolymers of 4-vinylcyclohexene dioxide."
↑ 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.
↑ 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.
↑ 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.
↑ 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.

[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. Bibcode:2008ChEuJ..14.7988H. doi:10.1002/chem.200800759. PMID 18618538.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[Alimardanov-2] 1 2 Kh. 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)

[Mukhamedova-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)

[GESTIS-4] 1 2 3 Record of CAS RN 106-87-6 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 24 March 2015.

[Ullmann-5] 1 2 3 4 Pham, 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.

[Hoyer-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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