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3,4-Epoxycyclohexanecarboxylate methyl ester

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3,4-Epoxycyclohexanecarboxylate methyl ester
Names
Preferred IUPAC name
Methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • COC(=O)C1CCC2C(C1)O2
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).

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

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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

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

References

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  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. ^ 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.
  4. ^ US 6201070  Naofumi Kumabe filing date 2001-03-13