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132888

Sigma-Aldrich

2-Chloro-4′-fluoroacetophenone

99%

Synonym(s):

ω-Chloro-4-fluoroacetophenone, 4-Fluorophenacyl chloride

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About This Item

Linear Formula:
FC6H4COCH2Cl
CAS Number:
456-04-2
Molecular Weight:
172.58
Beilstein:
637860
EC Number:
207-256-4
MDL number:
MFCD00011652
UNSPSC Code:
12352100
PubChem Substance ID:
24848083
NACRES:
NA.22

Assay

99%

form

solid

mp

47-50 °C (lit.)

SMILES string

Fc1ccc(cc1)C(=O)CCl

InChI

1S/C8H6ClFO/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4H,5H2

InChI key

UJZWJOQRSMOFMA-UHFFFAOYSA-N

Gene Information

human ... PTPN6(5777)

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General description

2-Chloro-4′-fluoroacetophenone on condensation with N-methyl-4-(methylthio)benzamidine yields 1-methyl-2-(4-methylthio)phenyl-4-(4-fluoro)phenylimidazole.

Application

2-Chloro-4′-fluoroacetophenone was used in the synthesis of S-(phenacyl)glutathiones and 2-[3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]-1-(4-fluorophenyl)ethanone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °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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Allergic contact dermatitis from 3-(alpha-methoxy) methylenebenzofuran-2(3H)-one (MBF) and alpha-chloro-4-fluoroacetophenone (CFAP) in chemical process workers.
M J Boffa et al.
Contact dermatitis, 34(6), 434-435 (1996-06-01)
2, 4, 5-Triarylimidazole inhibitors of IL-1 biosynthesis.
Gallagher TF, et al.
Bioorganic & Medicinal Chemistry Letters, 5(11), 1171-1176 (1995)
Donald M N Sikazwe et al.
Bioorganic & medicinal chemistry, 17(4), 1716-1723 (2009-01-22)
Arylcycloalkylamines, such as phenyl piperidines and piperazines and their arylalkyl substituents, constitute pharmacophoric groups exemplified in several antipsychotic agents. A review of previous reports indicates that arylalkyl substituents can improve the potency and selectivity of the binding affinity at D(2)-like
Philip G Board et al.
Chemical research in toxicology, 20(1), 149-154 (2007-01-18)
S-(Phenacyl)glutathione reductase (SPG-R) plays a significant role in the biotransformation of reactive alpha-haloketones to nontoxic acetophenones. Comparison of the apparent subunit size, amino acid composition, and catalysis of the reduction of S-(phenacyl)glutathiones indicated that a previously described rat SPG-R (Kitada
Justin D Smith et al.
Nature communications, 10(1), 1837-1837 (2019-04-25)
Photocatalytic polymers offer an alternative to prevailing organometallics and nanomaterials, and they may benefit from polymer-mediated catalytic and material enhancements. MPC-1, a polymer photoredox catalyst reported herein, exhibits enhanced catalytic activity arising from charge transfer states (CTSs) between its two

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