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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
$59.20
250 G
$114.95

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Available to ship onApril 28, 2025Details

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50 G
$59.20
250 G
$114.95

About This Item

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

$59.20

Available to ship onApril 28, 2025Details

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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].

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_germany

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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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
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
Zhinan Xu et al.
Applied microbiology and biotechnology, 70(1), 40-46 (2005-09-22)
Escherichia coli M15 (pQE30-car0210) was constructed to express carbonyl reductase (CAR) by cloning the car gene from Candida magnoliae and inserting it into pQE30. By cultivating E. coli M15 (pQE30-car0210) and M15 (pQE30-gdh0310), 8.2-fold and 12.3-fold enhancements in specific enzymatic
Hou Cao et al.
Bioresource technology, 102(2), 1733-1739 (2010-10-12)
A novel NADH-dependent dehydrogenases/reductases (SDRs) superfamily reductase (PsCRII) was isolated from Pichia stipitis. It produced ethyl (S)-4-chloro-3-hydroxybutanoate [(S)-CHBE] in greater than 99% enantiomeric excess. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by Q-Sepharose chromatography. Compared to
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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