Ethyl 4-chloroacetoacetate Chemical Properties

Melting point:

-8 °C

Boiling point:

115 °C/14 mmHg (lit.)

Density 

1.218 g/mL at 25 °C (lit.)

vapor pressure 

7hPa at 20℃

refractive index 

n20/D 1.452(lit.)

Flash point:

206 °F

storage temp. 

2-8°C

solubility 

47.0g/l

form 

Liquid

pka

9.56±0.46(Predicted)

color 

Clear colorless to pale reddish-yellow

PH

2.9 (10g/l, H2O, 20℃)

explosive limit

1.8%(V)

Water Solubility 

47.5 g/L (20 ºC)

BRN 

1761275

InChIKey

OHLRLMWUFVDREV-UHFFFAOYSA-N

LogP

0.68 at 25℃

CAS DataBase Reference

638-07-3(CAS DataBase Reference)

NIST Chemistry Reference

Butanoic acid, 4-chloro-3-oxo-, ethyl ester(638-07-3)

EPA Substance Registry System

Ethyl 4-chloroacetoacetate (638-07-3)

Safety Information

Hazard Codes 

T,N,C

Risk Statements 

25-34-51/53-24/25-36

Safety Statements 

26-36-45-61-36/37/39-27

RIDADR 

UN 2922 8/PG 2

WGK Germany 

3

RTECS 

AK5110000

F 

8-10-19-21

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29183000

MSDS

• Language:English Provider:Ethyl 4-chloro-3-oxobutanoate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 4-chloroacetoacetate Usage And Synthesis

Chemical Properties

Ethyl 4-chloroacetoacetate is colorless to pale reddish-yellow clear liquid

Uses

Ethyl-4-chloracetoacetate (CAAEt) is used as intermediate for organic syntheses, e.g. ethyl 4-chloro-3-arylaminocrotonates, diethyl succinylsuccinate, 2-alkyl-4-hydroxy-6-chloromethylpyrimidines, 4- chloromethylcoumarines. Product Data Sheet

Uses

Ethyl 4-chloroacetoacetate is used as a precursor in the preparation of phosphorous ylides. It finds application in regular film coating, pharmaceutical coating and formulation.

Preparation

Preparative Methods of Ethyl 4-chloroacetoacetate: the industrial production of the esters is made exclusively by chlorination of diketene followed by reaction of the intermediate acid chloride with the corresponding alcohol.^[2]

Solubility in organics

Ethyl 4-Chloroacetoacetate is is soluble in most organic solvents. The ethyl ester (1a) is 12% enolized in the pure liquid, and highly enolized (60% in CCl4) in nonpolar solvents.^[1]

storage

Ethyl 4-chloroacetoacetate is lachrymators of moderate toxicity; uses in a fume hood.

References

1. Rappoport, Z. The Chemistry of Enols; Wiley: New York, 1990; p 365.
2. Lonza AG; U.S. Patent 4 473 508, 1984 (CA 1985, 102, 5715).

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