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Merck

180769

Ethyl 4-chloroacetoacetate

95%

Synonym(s):

4-Chloro acetoethylacetate, Ethyl 4-chloro-3-oxobutanoate, Ethyl chloroacetoacetate

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About This Item

Linear Formula:
ClCH2COCH2CO2C2H5
CAS Number:
638-07-3
Molecular Weight:
164.59
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850895
EC Number:
211-317-0
Beilstein/REAXYS Number:
1761275
MDL number:
MFCD00000939

Product Name

Ethyl 4-chloroacetoacetate, 95%

InChI key

OHLRLMWUFVDREV-UHFFFAOYSA-N

InChI

1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3

SMILES string

CCOC(=O)CC(=O)CCl

assay

95%

form

liquid

refractive index

n20/D 1.452 (lit.)

bp

115 °C/14 mmHg (lit.)

density

1.218 g/mL at 25 °C (lit.)

functional group

chloro
ester
ketone

Quality Level

100

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Application

Ethyl 4-chloroacetoacetate was used in the synthesis of phosphorus ylides.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

206.6 °F - closed cup

flash_point_c

97 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8449
BCCJ8883
BCCJ0682
BCCD3226
BCCC8030

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Jer-Yiing Houng et al.
Biotechnology letters, 25(1), 17-21 (2003-07-29)
Amberlite XAD 2 resin enhanced the asymmetric reduction of ethyl 4-chloroacetoacetate (ECA) to S-4-chloro-3-hydroxybutyric acid ethyl ester as catalyzed by Saccharomyces cerevisiae. The absorbed ECA was released slowly to the solution during the reaction so that the substrate inhibition and
N Kizaki et al.
Applied microbiology and biotechnology, 55(5), 590-595 (2001-06-21)
The asymmetric reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to ethyl (S)-4-chloro-3-hydroxybutanoate ((S)-CHBE) was investigated. Escherichia coli cells expressing both the carbonyl reductase (S1) gene from Candida magnoliae and the glucose dehydrogenase (GDH) gene from Bacillus megaterium were used as the catalyst.
Tarjan Kaliaperumal et al.
Journal of industrial microbiology & biotechnology, 37(2), 159-165 (2009-11-10)
Asymmetric reduction of ethyl-4-chloro-3-oxobutanoate to (S)-ethyl-4-chloro-3-hydroxybutanoate in aqueous medium by resting cells of Candida parapsilosis ATCC 7330 was optimized. The influence of culture parameters (inoculum size, inoculum age and biocatalyst harvest time) and reaction parameters (co-substrate, resting cell, pH and
Hyun Joo Park et al.
Journal of microbiology and biotechnology, 20(9), 1300-1306 (2010-10-05)
Ethyl (R, S)-4-chloro-3-hydroxybutanoate (ECHB) is a useful chiral building block for the synthesis of L-carnitine and hypercholesterolemia drugs. The yeast reductase, YOL151W (GenBank locus tag), exhibits an enantioselective reduction activity, converting ethyl-4-chlorooxobutanoate (ECOB) exclusively into (R)-ECHB. YOL151W was generated in
Qi Ye et al.
Biotechnology letters, 31(4), 537-542 (2009-01-07)
An NADPH-dependent carbonyl reductase (PsCR) gene from Pichia stipitis was cloned. It contains an open reading frame of 849 bp encoding 283 amino acids whose sequence had less than 60% identity to known reductases that produce ethyl (S)-4-chloro-3-hydroxybutanoates (S-CHBE). When
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