Ethyl 2-oxocyclohexanecarboxylate Chemical Properties

Melting point:

101 °C

Boiling point:

106 °C/11 mmHg (lit.)

Density 

1.064 g/mL at 25 °C (lit.)

vapor pressure 

8.7Pa at 25℃

refractive index 

n20/D 1.477(lit.)

Flash point:

185 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

pka

12.06±0.20(Predicted)

form 

Oil

color 

Colourless

Water Solubility 

Soluble in water.

BRN 

608356

LogP

1.08

CAS DataBase Reference

1655-07-8(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexanecarboxylic acid, 2-oxo-, ethyl ester(1655-07-8)

EPA Substance Registry System

Cyclohexanecarboxylic acid, 2-oxo-, ethyl ester (1655-07-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26-36

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29183000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Ethyl 2-oxocyclohexanecarboxylate Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Ethyl 2-oxocyclohexanecarboxylate is used to produce other chemicals. For example, it can react with 4-methyl-aniline to get 2-oxo-cyclohexanecarboxylic acid p-toluidide. The reaction occurs with reagent DMAP

Uses

Ethyl 2-Oxocyclohexanecarboxylate is used in biocatalysis.

Reactions

The reaction of ethyl 2-oxo cyclohexane carboxylate (I) with phenyl vinyl sulphoxide (II) and sodium hydride followed by pyrolysis of the resulting phenyl sulphonyl ethyl compound (III) gives the 1-vinyl compound (IV).
Baeyer-Villiger oxidation of methyl 3- and 4-oxocyclohexanecarboxylates gave the expected hexanolides, whereas ethyl 2-oxocyclohexanecarboxylate(I) gave 5-ethoxyoxalylpentanoic acid by way of ethyl 1-hydroxy-2-oxocyclohexanecarboxylate, formed by epoxidation of the enol form of (I)[1-2].

Synthesis Reference(s)

Canadian Journal of Chemistry, 42, p. 1333, 1964 DOI: 10.1139/v64-205
The Journal of Organic Chemistry, 53, p. 878, 1988 DOI: 10.1021/jo00239a038
Tetrahedron Letters, 7, p. 2201, 1966

References

[1] A. Hubert, P. S. Starcher. “The Baeyer-Villiger oxidation of alkyl oxocyclohexanecarboxylates.” Journal of The Chemical Society C: Organic 377 1 (1968): 2500–2502.
[2] G. Koppel, M. D. Kinnick. “Phenyl vinyl sulphoxide, a vinyl carbonium ion synthetic equivalent.” Journal of The Chemical Society, Chemical Communications 27 1 (1975): 473–473.

Ethyl 2-oxocyclohexanecarboxylate(1655-07-8)Related Product Information

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