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105937

Sigma-Aldrich

3,4,4′-Trichlorocarbanilide

99%

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Synonym(s):
1-(4-Chlorophenyl)-3-(3,4-dichlorophenyl)urea, TCC, Triclocarban
Linear Formula:
Cl2C6H3NHCONHC6H4Cl
CAS Number:
101-20-2
Molecular Weight:
315.58
MDL number:
MFCD00013254
PubChem Substance ID:
24846715
NACRES:
NA.22

Agency

EPA 1694

Quality Level

100

vapor pressure

<0.1 mmHg ( 25 °C)

Assay

99%

form

solid

mp

254-256 °C (lit.)

solubility

methanol: soluble

application(s)

environmental

SMILES string

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

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)

InChI key

ICUTUKXCWQYESQ-UHFFFAOYSA-N

Gene Information

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

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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.

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.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Biodegradation of 3, 4, 4'-trichlorocarbanilide, TCC?, in sewage and activated sludge.
Gledhill WE.
Water Research, 9(7), 649-654 (1975)
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
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
Arjun K Venkatesan et al.
Journal of hazardous materials, 229-230, 29-35 (2012-06-30)
The antimicrobial agents triclosan (TCS), triclocarban (TCC) and their associated transformation products are of increasing concern as environmental pollutants due to their potential adverse effects on humans and wildlife, including bioaccumulation and endocrine-disrupting activity. Analysis by tandem mass spectrometry of
Niroj Aryal et al.
Water research, 45(17), 5545-5552 (2011-09-10)
Triclocarban and triclosan, two antimicrobials widely used in consumer products, can adversely affect ecosystems and potentially impact human health. The application of biosolids to agricultural fields introduces triclocarban and triclosan to soil and water resources. This research examined the phytoaccumulation
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