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180769

Sigma-Aldrich

Ethyl 4-chloroacetoacetate

95%

Synonym(s):

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

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50 G
€27.50
250 G
€92.80

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50 G
€27.50
250 G
€92.80

About This Item

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

€27.50

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Quality Level

100

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

SMILES string

CCOC(=O)CC(=O)CCl

InChI

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

InChI key

OHLRLMWUFVDREV-UHFFFAOYSA-N

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Application

Ethyl 4-chloroacetoacetate was used in the synthesis of phosphorus ylides[1].

Signal Word

Danger

Hazard Statements

H301 + H311,H314,H411

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8449
BCCJ8883
BCCJ0682
BCCD3226
BCCC8030

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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.
Applied microbiology and biotechnology, 87(2), 517-525 (2010-03-24)
To develop an economical industrial medium, untreated cane molasses (UCM) was tested as a carbon source for fermentation culturing of Escherichia coli. To test the industrial application of this medium, we chose a strain co-expressing a carbonyl reductase (PsCR) and
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
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.
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
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