Chemistry:3,4-Epoxycyclohexanecarboxylate methyl ester

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3,4-Epoxycyclohexanecarboxylate methyl ester
3,4-Epoxycyclohexancarboxylatmethylester.svg
Names
Preferred IUPAC name
Methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
Properties
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):

3,4-Epoxycyclohexanecarboxylate methyl ester refers to organic compounds with the formula C
6H
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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