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Sigma-Aldrich

1,1,3-Trichloroacetone

produced by Wacker Chemie AG, Burghausen, Germany, ≥86.5% (GC)

Synonym(s):

TCA, 1,1,3-Trichloro-2-propanone

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About This Item

Linear Formula:
(Cl)2CHCOCH2Cl
CAS Number:
921-03-9
Molecular Weight:
161.41
Beilstein/REAXYS Number:
1746647
MDL number:
MFCD00040500
UNSPSC Code:
12352100
PubChem Substance ID:
57646825
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

assay

≥86.5% (GC)

bp

88-90 °C/76 mmHg (lit.)

mp

9-11 °C (lit.)

density

1.512 g/mL at 20 °C (lit.)

SMILES string

ClCC(=O)C(Cl)Cl

InChI

1S/C3H3Cl3O/c4-1-2(7)3(5)6/h3H,1H2

InChI key

ZWILTCXCTVMANU-UHFFFAOYSA-N

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General description

1,1,3-Trichloroacetone is direct-acting mutagens in the Ames/Salmonella assay. It is precursor for the generation of 1,3-dihalo oxyallyl intermediates, which undergo [4 + 3] cycloadditions with a host of 1,3-diene systems.

Application

1,1,3-Trichloroacetone was used in base-induced solvolyses of [3.2.1]Bicyclic α,α′-dichloro ketones.

Other Notes

prices for bulk quantities on request

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B

wgk_germany

WGK 3

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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W F Blazak et al.
Mutation research, 206(4), 431-438 (1988-12-01)
1,1,1- and 1,1,3-trichloroacetones (TCA) result from the disinfection of municipal water supplies with chlorine, and are direct-acting mutagens in the Ames/Salmonella assay. The objective of this study was to further investigate the genotoxicity of these compounds in mammalian cells using
Ho Lam Chan et al.
Nature communications, 9(1), 3377-3377 (2018-08-25)
Polycomb repressive complex 1 (PRC1) plays essential roles in cell fate decisions and development. However, its role in cancer is less well understood. Here, we show that RNF2, encoding RING1B, and canonical PRC1 (cPRC1) genes are overexpressed in breast cancer.
Base-Induced Solvolyses of [3.2. 1] Bicyclic a, a'-Dichloro Ketones- 1, 3-Transposition and Ring-Contraction.
Fohlisch B, et al.
European Journal of Organic Chemistry, 2001(22), 4357-4365 (2001)
Yusheng Zhang et al.
Science advances, 6(23), eaaz7249-eaaz7249 (2020-06-18)
RING1B, a core Polycomb repressive complex 1 subunit, is a histone H2A ubiquitin ligase essential for development. RING1B is overexpressed in patients with luminal breast cancer (BC) and recruited to actively transcribed genes and enhancers co-occupied by the estrogen receptor
M Robinson et al.
Cancer letters, 48(3), 197-203 (1989-12-01)
Several chlorinated acetones have been identified in drinking water and these, as well as a number of chlorinated acroleins, are produced by chlorination of humic acid solutions. Many of these chlorinated compounds and the brominated acrolein analog were positive in
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