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690295

Sigma-Aldrich

Ethyl 4-chloroacetoacetate

Arxada quality, ≥97.0% (GC)

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
Beilstein:
1761275
EC Number:
211-317-0
MDL number:
MFCD00000939
UNSPSC Code:
12352100
PubChem Substance ID:
329761327
NACRES:
NA.22

Quality Level

100

Assay

≥97.0% (GC)

form

liquid

quality

Arxada quality

manufacturer/tradename

Arxada AG

impurities

≤0.04% metyl-4-chloroacetoacetate

refractive index

n20/D 1.452 (lit.)

bp

115 °C/14 mmHg (lit.)

density

1.218 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Saratani et al.
Bioscience, biotechnology, and biochemistry, 65(7), 1676-1679 (2001-08-23)
The enantioselectivity of ECAA to ECHB by eight fungi of four genus was evaluated. All strains showed (S)-selectivity, and Cylindrocarpon sclerotigenum IFO 31855 gave the highest yield and good optical purity (e.e.; >99%). Cell-free extract and acetone-dried cells of C.
K Kita et al.
Applied and environmental microbiology, 65(12), 5207-5211 (1999-12-03)
We cloned and sequenced the gene encoding an NADPH-dependent aldehyde reductase (ARII) in Sporobolomyces salmonicolor AKU4429, which reduces ethyl 4-chloro-3-oxobutanoate (4-COBE) to ethyl (S)-4-chloro-3-hydroxybutanoate. The ARII gene is 1,032 bp long, is interrupted by four introns, and encodes a 37,315-Da
M Kataoka et al.
Applied microbiology and biotechnology, 51(4), 486-490 (1999-05-26)
The asymmetric reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to ethyl (R)-4-chloro-3-hydroxybutanoate [(R)-CHBE] using Escherichia coli cells, which coexpress both the aldehyde reductase gene from Sporobolomyces salmonicolor and the glucose dehydrogenase (GDH) gene from Bacillus megaterium as a catalyst was investigated. In
Li-Juan Wang et al.
Bioresource technology, 102(14), 7023-7028 (2011-05-17)
An NADH-dependent reductase (ScCR) from Streptomyces coelicolor was discovered by genome mining for carbonyl reductases. ScCR was overexpressed in Escherichia coli BL21, purified to homogeneity and its catalytic properties were studied. This enzyme catalyzed the asymmetric reduction of a broad
Y Yasohara et al.
Bioscience, biotechnology, and biochemistry, 64(7), 1430-1436 (2000-08-17)
An NADPH-dependent carbonyl reductase (S1) isolated from Candida magnoliae catalyzed the reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to ethyl (S)-4-chloro-3-hydroxybutanoate (CHBE), with a 100% enantiomeric excess, which is a useful chiral building block for the synthesis of pharmaceuticals. The gene encoding
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