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Merck
CN

105937

3,4,4′-Trichlorocarbanilide

99%

Synonym(s):

1-(4-Chlorophenyl)-3-(3,4-dichlorophenyl)urea, TCC, Triclocarban

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About This Item

Linear Formula:
Cl2C6H3NHCONHC6H4Cl
CAS Number:
101-20-2
Molecular Weight:
315.58
NACRES:
NA.22
PubChem Substance ID:
24846715
UNSPSC Code:
12352100
MDL number:
MFCD00013254

Key Documents

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Product Name

3,4,4′-Trichlorocarbanilide, 99%

InChI

1S/C13H9Cl3N2O/c14-8-1-3-9(4-2-8)17-13(19)18-10-5-6-11(15)12(16)7-10/h1-7H,(H2,17,18,19)

SMILES string

Clc1ccc(NC(=O)Nc2ccc(Cl)c(Cl)c2)cc1

InChI key

ICUTUKXCWQYESQ-UHFFFAOYSA-N

agency

EPA 1694

vapor pressure

<0.1 mmHg ( 25 °C)

assay

99%

form

solid

mp

254-256 °C (lit.)

solubility

methanol: soluble

application(s)

environmental

functional group

amine
chloro

Quality Level

100

Gene Information

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Application

3,4,4′-Trichlorocarbanilide was used to develop a sensitive analytical method to determine triclocarban and environmental phenols in breast milk using isotope dilution on-line solid-phase extraction coupled with HPLC–tandem mass spectrometry. 3,4,4′-Trichlorocarbanilide was used in quantitative structure-activity relationship (QSAR)analyses conducted to study the co-occurrence of Triclocarban and Triclosan in U.S. Water Resources.

Biochem/physiol Actions

3,4,4′-Trichlorocarbanilide interferes with mammalian reproduction and can cause methemoglobinemia in humans.

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

General description

3,4,4′-Trichlorocarbanilide(TCC) is employed as bacteriostat and antimicrobial agent in bar soaps, cosmetics and other personal care prducts.TCC is a toxic, persistent and potentially bioaccumulative polychlorinated binuclear aromatic urea pesticide.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000188051
0000188051
MKCQ6353
MKCN8040
MKCG1042

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Rong Chu et al.
Oncotarget, 7(48), 78958-78970 (2016-10-16)
Microtubule targeting agents (MTAs) characteristically promote phosphorylation and degradation of Mcl-1, and this represents a critical pro-apoptotic signal in mitotic death. While several phosphorylation sites and kinases have been implicated in mitotic arrest-induced Mcl-1 phosphorylation, a comprehensive biochemical analysis has
Rolf U Halden et al.
Environmental science & technology, 39(6), 1420-1426 (2005-04-12)
Triclocarban (TCC) and triclosan (TCS) are antimicrobial additives in personal care products. Whereas TCS has been studied extensively, the environmental fate of TCC remains largely unknown. To address this data gap, we performed quantitative structure-activity relationship (QSAR) analyses that suggested
Biodegradation of 3, 4, 4'-trichlorocarbanilide, TCC?, in sewage and activated sludge.
Gledhill WE.
Water Research, 9(7), 649-654 (1975)
Nils Helge Schebb et al.
Aquatic toxicology (Amsterdam, Netherlands), 105(3-4), 448-454 (2011-08-30)
The antimicrobial triclocarban (TCC) is frequently found in personal care products and commonly observed in surface waters and sediments. Due to its long environmental persistence TCC accumulates in sewage sludge. It also shows a high unintended biological activity as a
Jian-Liang Zhao et al.
Water research, 47(1), 395-405 (2012-11-07)
Triclosan (TCS) and triclocarban (TCC) are two commonly used personal care products. They may enter into aquatic environments after consumption and pose potential risks to aquatic organisms. We investigated the occurrence and fate of TCS and TCC in five large
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