| Identification | More | [Name]
Ethyl 4-chloroacetoacetate | [CAS]
638-07-3 | [Synonyms]
4-CHLOROACETOACETIC ACID ETHYL ESTER
AKOS BBS-00004336
BUTANOIC ACID, 4-CHLORO-3-OXO-ETHYL ESTER
ETHYL 4-CHLORO-3-OXOBUTANOATE
ETHYL 4-CHLOROACETOACETATE
ETHYL-GAMMA-CHLOROACETOACETATE
4-chloro-3-oxo-butanoicaciethylester
4-chloro-acetoaceticaciethylester
Acetoacetic acid, 4-chloro-, ethyl ester
Ethyl4-Chloroacetoacetate.TheIntermediateOfAmlodipine,ForStatins(Lipitor,CrestorEtc)
Ethyl4-chloroacetoacetate,97%
4-Chloro-acetoacetic
Ethyl-4-chloracetoacetat
4-chloro-3-oxo-butanoic acid ethyl ester
4-CHLOROACETOACETIC ACID ETHYL ESTER 95%
Ethyl 4-chloro-3-oxobutyrate
Ethyl (chloroacetyl)acetate
Ethyl g-chloroacetoacetate
Ethyl 4-chloroacetoacetate ,98%
(Chloroacetyl)acetic acid ethyl ester | [EINECS(EC#)]
211-317-0 | [Molecular Formula]
C6H9ClO3 | [MDL Number]
MFCD00000939 | [Molecular Weight]
164.59 | [MOL File]
638-07-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to pale reddish-yellow clear liquid | [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.)
| [Fp ]
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) | [Usage]
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 | [Detection Methods]
GC,NMR | [BRN ]
1761275 | [InChI]
1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3 | [InChIKey]
OHLRLMWUFVDREV-UHFFFAOYSA-N | [SMILES]
CCOC(=O)CC(=O)CCl | [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]
638-07-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS05,GHS06,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H301+H311-H314-H411 | [Precautionary statements ]
P270-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 | [Hazard Codes ]
T,N,C | [Risk Statements ]
R25:Toxic if swallowed.
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R24/25:Toxic in contact with skin and if swallowed .
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
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 | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29183000 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Oral
Aquatic Chronic 2
Eye Dam. 1
Skin Corr. 1B |
| Hazard Information | Back Directory | [Description]
Ethyl 4-chloroacetoacetate is a chemical compound, which for the ethyl
esters of acetoacetic acid belongs. It is a starting material in various
syntheses. | [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
| [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]
| [Synthesis]
GENERAL PROCEDURE: To an anhydrous THF (2 mL) solution of diisopropylamine (340 μL, 2.4 eq.) in a flame-dried round-bottomed flask under an argon atmosphere at 0 °C, n-butyllithium (1.4 mL, 1.6 M hexane solution, 2.2 eq.) was slowly added and the reaction mixture was stirred at this temperature for 15 min. Maintaining the same temperature, a solution of THF (2 mL) in ethyl acetoacetate (1 mmol) was slowly added dropwise. The reaction mixture was cooled to -78 °C after continued stirring at 0 °C for 1 h. Methyl chlorosulfate (110 μL, 1.2 eq.) was subsequently added. After stirring at -78 °C for 30 min, the reaction was quenched by the addition of saturated aqueous ammonium chloride solution (5 mL). The mixture was extracted with dichloromethane (3 x 5 mL) and the organic phases were combined and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave the target product ethyl 4-chloroacetoacetate. | [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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