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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:
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.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000375888
0000372760
0000375888
0000372760
0000213683

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Experimental study of the adsorption of 2-Chloroacetophenone at the air-environmental water interface
Hao, et al.
Frontiers in environmental science., 10, 2254-2254 (2022)
Preparation of microgel-supported chiral catalysts and their application in the asymmetric hydrogenation of aromatic ketones
Deng J, et al.
Reactive and Functional Polymers, 72, 378-382 (2012)
Bert Brône et al.
Toxicology and applied pharmacology, 231(2), 150-156 (2008-05-27)
The TRPA1 channel is activated by a number of pungent chemicals, such as allylisothiocyanate, present in mustard oil and thiosulfinates present in garlic. Most of the known activating compounds contain reactive, electrophilic chemical groups, reacting with cysteine residues in the
Lenilson C Rocha et al.
Biotechnology letters, 31(10), 1559-1563 (2009-06-06)
The asymmetric reduction of 2-chloro-1-phenylethanone (1) by seven strains of marine fungi was evaluated and afforded (S)-(-)-2-chloro-1-phenylethanol with, in the best case, an enantiomeric excess of 50% and an isolated yield of 60%. The ability of marine fungi to catalyse
Anil K Nigam et al.
Journal of hazardous materials, 184(1-3), 506-514 (2010-09-17)
Pyrolysis-GC/MS system with on-line micro-furnace was used to make rapid evaluation of ω-chloroacetophenone (CN) decomposition under inert thermal atmospheres. The volatile products evolved during pyrolysis were analyzed by thermal gravimetric analysis (TGA) and Py-GC/MS to obtain specific thermogram and pyrogram.
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