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183709

Sigma-Aldrich

2′-Chloroacetophenone

97%

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About This Item

Linear Formula:
ClC6H4COCH3
CAS Number:
2142-68-9
Molecular Weight:
154.59
Beilstein:
1858916
EC Number:
218-397-6
MDL number:
MFCD00000560
UNSPSC Code:
12352100
PubChem Substance ID:
24851071
NACRES:
NA.22

Assay

97%

form

liquid

bp

227-230 °C

density

1.190 g/mL at 20 °C

SMILES string

CC(=O)c1ccccc1Cl

InChI

1S/C8H7ClO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H3

InChI key

ZDOYHCIRUPHUHN-UHFFFAOYSA-N

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General description

2′-Chloroacetophenone undergoes stereoselective reduction to (R)-2′-chloro-1-phenyl-ethanol by Saccharomyces cerevisiae B5. It is commonly used as lacrimator.

Application

2′-Chloroacetophenone was employed as model substrate to investigate the enzymatic performance of Aspergillus terreus and Rhizopus oryzae in enantioselective bioreductions using glycerol as a co-solvent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

190.4 °F

Flash Point(C)

88 °C

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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K E Ferslew et al.
Journal of forensic sciences, 31(2), 658-665 (1986-04-01)
2-Chloroacetophenone (CN) and o-chlorobenzylidene malononitrile (CS) are the most common chemical agents used as lacrimators in the United States. There is a lack of complete spectral data on these compounds in the literature. Spectral data (ultraviolet, fluorescence, proton nuclear magnetic
Hui Song et al.
Journal of chromatographic science, 57(4), 299-304 (2019-02-06)
The synthetic condition of tulobuterol was optimized to gain lower impurity content. Two intermediates were analyzed, and three degradation impurities were isolated using preparative liquid chromatography for the first time and subsequently characterized by various techniques. Possible degradation impurities were
Improving the enantioselective bioreduction of aromatic ketones mediated by Aspergillus terreus and Rhizopus oryzae: the role of glycerol as a co-solvent.
Andrade LH, et al.
Tetrahedron Asymmetry, 20(13), 1521-1525 (2009)
Zhi-Min Ou et al.
Sheng wu gong cheng xue bao = Chinese journal of biotechnology, 19(2), 206-211 (2005-06-22)
(R)-chlorprenaline, a selective activator of beta2 receptor and an effective drug for bronchitis and asthma, is industrially prepared from (R)-2'-chloro-1-phenyl-ethanol. In this communication, we describe (1) the identification of Saccharomyces cerevisiae B5 as an effective host for stereoselective reduction of
Kunpeng Li et al.
Scientific reports, 7(1), 3081-3081 (2017-06-10)
(S)-carbonyl reductase II (SCRII) from Candida parapsilosis is a short-chain alcohol dehydrogenase/reductase. It catalyses the conversion of 2-hydroxyacetophenone to (S)-1-phenyl-1,2-ethanediol with low efficiency. Sortase was reported as a molecular "stapler" for site-specific protein conjugation to strengthen or add protein functionality.

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