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638-07-3

Basic Information
CAS No.: 638-07-3
Name: Ethyl 4-chloroacetoacetate
Article Data: 21
Cas Database
Molecular Structure:
Molecular Structure of 638-07-3 (Ethyl 4-chloroacetoacetate)
Formula: C6H9ClO3
Molecular Weight: 164.589
Synonyms: Acetoaceticacid, 4-chloro-, ethyl ester (7CI,8CI);4-Chloro acetoethylacetate;4-Chloro-3-oxobutanoic acid ethyl ester;4-Chloro-3-oxobutyric acid ethylester;4-Chloroacetoacetic acid ethyl ester;Ethyl (chloroacetyl)acetate;Ethyl3-oxo-4-chlorobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl4-chloro-3-oxobutyrate;Ethyl g-chloroacetoacetate;Ethyl w-chloroacetoacetate;g-Chloroacetoacetic acid ethyl ester;
EINECS: 211-317-0
Density: 1.179 g/cm3
Melting Point: -8 °C
Boiling Point: 235.5 °C at 760 mmHg
Flash Point: 96.7 °C
Solubility: 47.5 g/L (20 ºC) in water
Appearance: Colorless to pale reddish-yellow clear liquid
Hazard Symbols: ToxicT, DangerousN, CorrosiveC
Risk Codes: 25-34-51/53-24/25-36
Safety: 26-36-45-61-36/37/39-27
Transport Information: UN 2922 8/PG 2
PSA: 43.37000
LogP: 0.74750
Synthetic route
141-97-9

ethyl acetoacetate

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
Stage #1: ethyl acetoacetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
100%
141-78-6

ethyl acetate

105-39-5

chloroacetic acid ethyl ester

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
In ethanol; dimethyl sulfoxide at 128 - 152℃; under 3648.24 - 6840.46 Torr; for 22h; Temperature; Pressure; Inert atmosphere;98.7%
141-78-6

ethyl acetate

96-34-4

methyl chloroacetate

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 110 - 145℃; under 2280.15 - 6080.41 Torr; for 15h; Inert atmosphere;97.3%
674-82-8

4-methyleneoxetan-2-one

64-17-5

ethanol

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
Stage #1: 4-methyleneoxetan-2-one With chlorine In dichloromethane under 225.023 Torr; Flow reactor;
Stage #2: ethanol at 40 - 70℃; under 712.571 Torr; for 4h;
93%
Stage #1: 4-methyleneoxetan-2-one With chlorine; sodium hydroxide; copper dichloride In dichloromethane at -40 - 10℃;
Stage #2: ethanol In dichloromethane Temperature;
90%
591-78-6

n-hexan-2-one

6082-74-2

4,4-dichloro-3-oxobutyric acid ethyl ester

A

638-07-3

ethyl (2-chloroaceto)acetate

B

(Z)-5-Methyl-3-oxo-non-4-enoic acid ethyl ester

Conditions
ConditionsYield
With iron pentacarbonyl In benzene at 80℃; Reformatsky-type addition;A 75 % Chromat.
B n/a
591-78-6

n-hexan-2-one

6082-74-2

4,4-dichloro-3-oxobutyric acid ethyl ester

A

638-07-3

ethyl (2-chloroaceto)acetate

B

141-97-9

ethyl acetoacetate

Conditions
ConditionsYield
With iron pentacarbonyl; water; N,N-dimethyl-formamide In benzene at 80℃;A 40 % Chromat.
B 16 % Chromat.
6082-74-2

4,4-dichloro-3-oxobutyric acid ethyl ester

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
With iron pentacarbonyl; water In benzene at 80℃;65 % Chromat.
6082-74-2

4,4-dichloro-3-oxobutyric acid ethyl ester

100-52-7

benzaldehyde

A

638-07-3

ethyl (2-chloroaceto)acetate

B

1503-99-7

ethyl 3-oxo-5-phenylpent-4-enoate

Conditions
ConditionsYield
With iron pentacarbonyl In benzene at 80℃; Reformatsky-type addition;A 70 % Chromat.
B n/a
41295-64-1

4-chloroacetoacetyl chloride

64-17-5

ethanol

638-07-3

ethyl (2-chloroaceto)acetate

Conditions
ConditionsYield
Stage #1: 4-chloroacetoacetyl chloride; ethanol Industry scale;
Stage #2: With sodium hydroxide In water Product distribution / selectivity;
In dichloromethane156.3 g
150-19-6

O-methylresorcine

638-07-3

ethyl (2-chloroaceto)acetate

41295-55-0

4-(chloromethyl)-7-methoxy-2H-chromen-2-one

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;100%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.5h; Pechmann condensation reaction;96%
With perchloric acid; sulfuric acid at 25℃;95.2%
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Chemistry

Product Name: Ethyl 4-chloroacetoacetate (CAS NO.638-07-3)

Molecular Formula: C6H9ClO3
Molecular Weight: 164.59g/mol
Mol File: 638-07-3.mol
EINECS: 211-317-0
Appearance: Colorless to pale reddish-yellow clear liquid
Melting Point: -8 °C
Boiling point: 235.5 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 96.7 °C
Density: 1.179 g/cm3
Refractive index: n20/D 1.452(lit.)
Water Solubility: 47.5 g/L (20 ºC)
Index of Refraction: 1.436 
Molar Refractivity: 36.49 cm3 
Molar Volume: 139.5 cm3 
Surface Tension: 34.8 dyne/cm
Enthalpy of Vaporization: 47.23 kJ/mol
Vapour Pressure: 0.0498 mmHg at 25°C
XLogP3-AA: 0.9
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Ethyl 4-chloroacetoacetate (CAS NO.638-07-3):
  IUPAC Name: ethyl 4-chloro-3-oxobutanoate
  Canonical SMILES: CCOC(=O)CC(=O)CCl
  InChI: InChI=1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3 
  InChIKey: OHLRLMWUFVDREV-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; Halogen compounds; C6 to C7; Carbonyl Compounds; Esters

Uses

 Ethyl 4-chloroacetoacetate (CAS NO.638-07-3) can be used in medicine and pesticide intermediates.

Toxicity Data With Reference

1.    

ipr-rat LD50:108 mg/kg

    OYYAA2    Oyo Yakuri. Pharmacometrics. 33 (1987),695.
2.    

ipr-mus LD50:88 mg/kg

    OYYAA2    Oyo Yakuri. Pharmacometrics. 33 (1987),695.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of Ethyl 4-chloroacetoacetate (CAS NO.638-07-3):
Hazard Codes: TToxic,NDangerous,CCorrosive
Risk Statements: 25-34-51/53-24/25-36  
R25 :Toxic if swallowed. 
R34:Causes burns. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R24:Toxic in contact with skin. 
R25 :Toxic if swallowed. R36:Irritating to eyes.
Safety Statements: 26-36-45-61-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: AK5110000
F: 8-10-19-21
HazardClass: 8
PackingGroup: II
HS Code: 29183000

Specification

 Ethyl 4-chloroacetoacetate , its CAS NO. is 638-07-3, the synonyms are Butanoic acid, 4-chloro-3-oxo-, ethyl ester ; Ethyl 4-chloro-3-oxobutanoate ; Ethyl gamma-chloroacetoacetate ; Acetoacetic acid, 4-chloro-, ethyl ester .