3,4-Epoxycyclohexanecarboxylate methyl ester

3,4-Epoxycyclohexanecarboxylate methyl ester
Names
	Preferred IUPAC name Methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate
Identifiers
CAS Number	41088-52-2;
3D model (JSmol)	Interactive image;
ChemSpider	11227215;
PubChem CID	12770164;
CompTox Dashboard (EPA)	DTXSID00884680 ;
	InChI InChI=1S/C8H12O3/c1-10-8(9)5-2-3-6-7(4-5)11-6/h5-7H,2-4H2,1H3 Key: QCGKUFZYSPBMAY-UHFFFAOYSA-N;
	SMILES COC(=O)C1CCC2C(C1)O2;
Properties
Chemical formula	C8H12O3
Molar mass	156.181 g·mol−1
Appearance	Colorless liquid
Boiling point	109.5–110.5 °C (229.1–230.9 °F; 382.6–383.6 K) (17 mmHg)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,4-Epoxycyclohexanecarboxylate methyl ester refers to organic compounds with the formula C₆H₉OCO₂CH₃. These are bifunctional compounds consisting of an ester and cycloaliphatic epoxide groups. It exists as two diastereomers both of which are chiral. These species are of interest in polymer chemistry.

Synthese and reactions

3,4-Epoxycyclohexanecarboxylate methyl ester is prepared by epoxidation of 4-cyclohexenecarboxylate methyl ester with peracid.^[3] It is a crosslinking agent in the production of epoxy resins.^[3]^[4] 3,4-Epoxycyclohexanecarboxylate methyl ester itself would give a linear polymer when homopolymerized.

Properties

3,4-Epoxycyclohexanecarboxylate methyl ester has a viscosity of 6 mPa·s.^[3]

References

^ James V. Crivello, Ulrike Varlemann (October 1995). "Mechanistic study of the reactivity of 3,4-epoxycyclohexylmethyl 3′,4′-epoxycyclohexancarboxylate in photoinitiated cationic polymerizations". Journal of Polymer Science Part A: Polymer Chemistry. 33 (14): 2473–2486. doi:10.1002/pola.1995.080331421.
^ Norman A. Nelson , George A. Mortimer (October 1957). "Bicyclo[3.1.0]hexane Derivatives. I. Synthesis of Bicyclo[3.1.0]-2-hexanone and Methyl Bicyclo[3.1.0]hexane-1-carboxylate". The Journal of Organic Chemistry. 22 (10): 1146–1153. doi:10.1021/jo01361a003.
^ ^a ^b ^c Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_547.pub2. ISBN 9783527303854.
^ US 6201070 Naofumi Kumabe filing date 2001-03-13

[1] James V. Crivello, Ulrike Varlemann (October 1995). "Mechanistic study of the reactivity of 3,4-epoxycyclohexylmethyl 3′,4′-epoxycyclohexancarboxylate in photoinitiated cationic polymerizations". Journal of Polymer Science Part A: Polymer Chemistry. 33 (14): 2473–2486. doi:10.1002/pola.1995.080331421.

[NELSON-2] Norman A. Nelson , George A. Mortimer (October 1957). "Bicyclo[3.1.0]hexane Derivatives. I. Synthesis of Bicyclo[3.1.0]-2-hexanone and Methyl Bicyclo[3.1.0]hexane-1-carboxylate". The Journal of Organic Chemistry. 22 (10): 1146–1153. doi:10.1021/jo01361a003.

[Ullmann-3] Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_547.pub2. ISBN 9783527303854.

[4] US 6201070 Naofumi Kumabe filing date 2001-03-13

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