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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:
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.)

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

Signal Word

Danger

Hazard Statements

H315,H317,H318,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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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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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