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Sigma-Aldrich

2,2′,4′-Trichloroacetophenone

97%

Synonym(s):

ω,2,4-Trichloroacetophenone, 2,4-Dichlorophenacyl chloride

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About This Item

Linear Formula:
Cl2C6H3COCH2Cl
CAS Number:
4252-78-2
Molecular Weight:
223.48
Beilstein/REAXYS Number:
957098
EC Number:
224-218-2
MDL number:
MFCD00000934
UNSPSC Code:
12352100
PubChem Substance ID:
24849802
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

bp

130-135 °C/4 mmHg (lit.)

mp

47-54 °C (lit.)

functional group

chloro
ketone

SMILES string

ClCC(=O)c1ccc(Cl)cc1Cl

InChI

1S/C8H5Cl3O/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3H,4H2

InChI key

VYWPPRLJNVHPEU-UHFFFAOYSA-N

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General description

2,2′,4′-Trichloroacetophenone is an α-haloketone. It undergoes reduction to 2′,4′-dichloroacetophenone by glutathione-dependent cytosolic enzymes present in the liver, kidney and brain. It participates in the microwave induced N-alkylation of several azoles to afford the corresponding 1-(2′,4′-dichlorophenacyl)azoles.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4004
STBJ5489
STBJ5031
S70875
00928JJ

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Clean and efficient microwave-solvent-free synthesis of 1-(2', 4'-dichlorophenacyl) azoles.
Perez ER, et al.
Tetrahedron, 59(6), 865-870 (2003)
A Brundin et al.
Biochemical pharmacology, 31(23), 3885-3890 (1982-12-01)
alpha-Haloketones are highly reactive compounds, which are known to undergo enzymatic reduction to methyl ketones. The objective of this research was to characterize the enzymes involved in this reaction and to investigate the mechanism of the reaction. 2,2',4'-Trichloroacetophenone was reduced
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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