159255
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:
Molecular Weight:
223.48
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
224-218-2
Beilstein/REAXYS Number:
957098
MDL number:
Assay:
97%
Form:
solid
InChI key
VYWPPRLJNVHPEU-UHFFFAOYSA-N
InChI
1S/C8H5Cl3O/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3H,4H2
SMILES string
ClCC(=O)c1ccc(Cl)cc1Cl
assay
97%
form
solid
bp
130-135 °C/4 mmHg (lit.)
Quality Level
functional group
chloro, ketone
Related Categories
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
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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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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