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

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[1]
Boiling point |  109.5–110.5 °C (229.1–230.9 °F; 382.6–383.6 K)[2] (17 mmHg)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

3,4-Epoxycyclohexanecarboxylate methyl ester refers to organic compounds with the formula C

9OCO
2CH
3. 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

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.
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.
3. ↑ 3.0 3.1 3.2 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 patent 6201070 Naofumi Kumabe filing date 2001-03-13

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*[CID]: Compound ID