Chlorodifluoroacetic acid ethyl ester Chemical Properties

Boiling point:

96-97.5 °C (lit.)

Density 

1.252 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.358(lit.)

Flash point:

65 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Sparingly)

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.252

Sensitive 

Moisture Sensitive

BRN 

1761413

InChI

InChI=1S/C4H5ClF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

InChIKey

GVCAWQUJCHZRCB-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(Cl)(F)F

CAS DataBase Reference

383-62-0(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, chlorodifluoro-, ethyl ester (383-62-0)

Safety Information

Hazard Codes 

F,C,Xi

Risk Statements 

11-34-20/21/22

Safety Statements 

16-26-27-36/37/39-45

RIDADR 

UN 2924 3/PG 2

WGK Germany 

3

Hazard Note 

Flammable

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29159000

MSDS

• Language:English Provider:Chlorodifluoroacetic acid ethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Chlorodifluoroacetic acid ethyl ester Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

Ethyl chlorodifluoroacetate (ECDFA) may be used as a starting reagent in the synthesis of 3-gem-difluoro-2-ethoxy allylic alcohols.

General Description

Ethyl chlorodifluoroacetate (ECDFA) undergoes Reformatskii reaction with various aldehydes in DMF. It reacts with phenylacetylene to afford ethyl α,α?difluoro-4-phenyl-3-butenoates.

Synthesis

General procedure for the synthesis of ethyl difluorochloroacetate from ethanol and difluorochloroacetic acid: 504.3 g (3.87 mmol) of difluorochloroacetic acid and 5.0 g of p-toluenesulfonic acid were dissolved in 775 mL of dichloromethane, and 311.6 g (6.76 mol) of ethanol was slowly added over a 30-minute period at room temperature (the temperature was raised to 33 °C during the reaction). The mixture was assembled to a water condenser and stirred at reflux for 38 hours and then cooled to room temperature. The reaction mixture was washed sequentially with 200 mL of water, 200 mL of saturated sodium bicarbonate solution and 200 mL of water, followed by drying with anhydrous sodium sulfate, filtration and distillation. Further purification by fractional distillation afforded 488.9 g (98% purity, 78.5% yield) of ethyl difluorochloroacetate with a boiling point of 94-96 °C.

References

[1] Patent: WO2005/3077, 2005, A1. Location in patent: Page 13
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 4174,4177

Chlorodifluoroacetic acid ethyl ester(383-62-0)Related Product Information

• Difluorochloromethane
• Ethyl difluoroacetate
• Difluoroacetic acid
• METHYL DIFLUOROACETATE
• DIFLUOROACETIC ANHYDRIDE
• Ethyl bromodifluoroacetate
• Sodium chlorodifluoroacetate
• Diethyl 2,2-difluoromalonate
• Ethyl fluoroacetate
• Chlorodifluoroacetic acid ethyl ester
• Chlorofluoromethane
• Chlorodifluoroacetic acid
• CHLORODIFLUOROACETIC ANHYDRIDE
• 1-CHLORO-1-FLUOROETHANE
• CHLOROFLUOROACETIC ACID
• Ethyl chloroacetate
• 2-Chloroethyl ethyl ether
• Chloroacetic acid