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Sigma-Aldrich

2-Chloroacetophenone

purum, ≥98.0% (GC)

Synonym(s):

ω-Chloroacetophenone, Phenacyl chloride

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About This Item

Linear Formula:
C6H5COCH2Cl
CAS Number:
532-27-4
Molecular Weight:
154.59
Beilstein/REAXYS Number:
507950
EC Number:
208-531-1
MDL number:
MFCD00000933
UNSPSC Code:
12352100
PubChem Substance ID:
329767699
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥98.0% (GC)

form

crystals

bp

244-245 °C (lit.)

mp

53-56 °C
54-56 °C (lit.)

density

1.324 g/mL at 25 °C (lit.)

SMILES string

ClCC(=O)c1ccccc1

InChI

1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

InChI key

IMACFCSSMIZSPP-UHFFFAOYSA-N

Gene Information

human ... PTPN6(5777)

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General description

2-Chloroacetophenone is an organic building block used in the synthesis of heterocyclic compounds. It has low solubility in water but can be soluble in alcohols, ethers and other organic solvents.

Application

2-Chloroacetophenone can be used in the synthesis of phenyl acetic acid by Photo-Favorskii rearrangement. It is also used in the preparation of 1-(2-chlorophenyl)ethanol via asymmetric hydrogenation reaction.

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL2353V
BCCF4647
BCCD8619
BCCD6990
BCCB0484

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Target reaction-oriented screening from soil samples yielded a ketone reductase-producing Bacillus sp., strain ECU0013, which exhibits excellent stereoselectivity, high substrate tolerance and is capable of regenerating the required cofactor with glucose as a co-substrate. Whole-cells catalyzed the asymmetric reduction of
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Biotechnology progress, 22(5), 1301-1304 (2006-10-07)
The asymmetric reduction of o-chloroacetophenone 1 with Candida pseudotropicalis 104 produced the corresponding (S)-1-(2-chloro-phenyl)-ethanol 2 with the enantiomeric excess (ee >99%) without addition of any cosolvent. The cell could tolerate high ketone 1 concentration of 233.8 mmol/L (i.e., 36 g/L)
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Regulatory toxicology and pharmacology : RTP, 36(1), 1-11 (2002-10-18)
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