Ethyl chlorooxoacetate Chemical Properties

Melting point:

156-158 °C(Solv: ethanol (64-17-5))

Boiling point:

135 °C

Density 

1.222 g/mL at 25 °C(lit.)

refractive index 

1.416-1.418

Flash point:

41 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Chloroform

form 

Liquid

color 

Clear

Specific Gravity

1.222

Water Solubility 

Slightly miscible with water.

Sensitive 

Moisture Sensitive

BRN 

506725

InChIKey

OWZFULPEVHKEKS-UHFFFAOYSA-N

CAS DataBase Reference

4755-77-5(CAS DataBase Reference)

NIST Chemistry Reference

Chlorooxalic acid, ethyl ester(4755-77-5)

EPA Substance Registry System

Acetic acid, chlorooxo-, ethyl ester (4755-77-5)

Safety Information

Hazard Codes 

C,F

Risk Statements 

34-29-20/21/22-14-10-37-36

Safety Statements 

8-45-36/37/39-26-16

RIDADR 

2920

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29171990

MSDS

• Language:English Provider:Chlorooxalic acid ethyl ester
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl chlorooxoacetate Usage And Synthesis

Uses

Ethyl oxalyl monochloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. Ethyl oxalyl monochloride acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor.

Description

Ethyl chlorooxoacetate has been used as a reactant in the preparation of oxyoxalamide derivatives as epoxide hydrolase inhibitors.

Chemical Properties

clear liquid

Uses

Ethyl oxalyl chloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. It acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor.

Uses

Ethyl chlorooxoacetate can be used for the synthesis of:

• α-keto esters.
• Functionalized 3-pyrolin-2-ones.
• Substituted arylglyoxylic acids via Friedel–Crafts acylation.
• Substituted 9,10-phenanthrenequinones.
• Quinoxalinone derivatives.

reaction suitability

reagent type: oxidant

Synthesis

The general procedure for the synthesis of monoethyl oxalyl chloride from diethyl oxalate was as follows: a mixture of potassium acetate (20 g), water (30 mL) and diethyl oxalate (29.2 g, 0.2 mol) was stirred and reacted for 2 hours at 70-80 °C. Upon completion of the reaction, the reaction mixture was cooled and concentrated to 30 mL. Subsequently, ethanol (50 mL) and ether (150 mL) were added and the mixed solution was filtered to afford 23.61 g of potassium monoethyl oxalate (76% yield). The dried potassium monoethyl oxalate (20.6 g, 0.13 mol) was pre-mixed with diethyl ether (20 mL) in an ice bath and SOCl2 (30 g, 0.25 mol) was added slowly. The reaction mixture was heated under reflux conditions for 15 hours. At the end of the reaction, the resulting white solid of potassium chloride was removed by filtration, the filtrate was separated and the 125-130 °C fraction was collected by distillation to give 12.22 g of monoethyl oxalyl chloride (69% yield).

References

[1] Gazzetta Chimica Italiana, 1891, vol. 21 I, p. 306
[2] Monatshefte fuer Chemie, 1905, vol. 26, p. 375
[3] Chemische Berichte, 1886, vol. 19, p. 2159
[4] Justus Liebigs Annalen der Chemie, 1889, vol. 254, p. 27
[5] Recueil des Travaux Chimiques des Pays-Bas, 1907, vol. 26, p. 381

Ethyl chlorooxoacetate(4755-77-5)Related Product Information

• METHYL OXALYL CHLORIDE
• Tris(trimethylsilyl)phosphate
• Sulfuryl chloride
• Ethyl acetate
• BUTYL OLEATE
• Tosyl chloride
• Chloroacetyl chloride
• Oxalyl chloride
• Ethyl propiolate
• Ethyl cyanoacetate
• Monoethyl fumarate
• Diethyl oxalate
• Ethylparaben
• Benzoyl chloride
• ISOXADIFEN-ETHYL
• Ethanol
• Ethyl acrylate
• Trinexapac-ethyl
• Ethyl Oxalyl Chloride