4640-01-1

Basic information

• Product Name: TRICLOSAN METHYL ETHER
• Synonyms: TRICLOSAN METHYL ETHER;METHYL ETHER TRICLOSAN;Triclosan-methyl OEKANAL;2,4,4'-trichloro-2'-hydroxydiphenyl methyl ether;2,4,4μ-Trichloro-2μ-methoxydiphenyl ether, 5-Chloro-2-(2,4-dichlorophenoxy)anisole, Methyl triclosan;Triclosan-methyl;Benzene, 4-chloro-1-(2,4-dichlorophenoxy)-2-methoxy-;Methyl triclosan
• CAS NO: 4640-01-1
• Molecular Formula: C₁₃H₉Cl₃O₂
• Molecular Weight: 303.57
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 4640-01-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 210-217 °C
• Boiling Point: 358.7 °C at 760 mmHg
• Flash Point: 128.5 °C
• Appearance: colourless syrup
• Density: 1.38 g/cm³
• Vapor Pressure: 5.18E-05mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Refrigerator
• CAS DataBase Reference: TRICLOSAN METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: TRICLOSAN METHYL ETHER(4640-01-1)
• EPA Substance Registry System: TRICLOSAN METHYL ETHER(4640-01-1)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3082 9/PG 3
• Hazardous Substances Data: 4640-01-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Syrup

Uses

A bactericide detected in rivers and lakes. The current lot contains 8.7% d2, 0.2% d1 and 0.002% d0.

InChI:InChI=1/C13H9Cl3O2/c1-17-13-7-9(15)3-5-12(13)18-11-4-2-8(14)6-10(11)16/h2-7H,1H3

Upstream product

• 3380-34-5 triclosan 
• 74-88-4 methyl iodide 
• 300350-24-7 2,4,4'-trichloro-2'-bromodiphenyl ether 
• 186581-53-3 diazomethane 

Relevant articles and documents

Occurrence of Methyl Triclosan, a Transformation Product of the Bactericide Triclosan, in Fish from Various Lakes in Switzerland

The bactericide triclosan and methyl triclosan, an environmental transformation product thereof, have been previously detected in lakes and a river in Switzerland. Both compounds are emitted via wastewater treatment plants (WWTPs), with methyl triclosan probably being formed by biological methylation. Passive sampling with semi-permeable membrane devices (SPMDs) showed the presence of methyl triclosan in some lakes, suggesting some potential for bioaccumulation of the compound. In this study, we report the presence of methyl triclosan in fish (white fish, coregonus sp.; roach, rutilus rutilus) from various lakes in Switzerland receiving inputs from WWTPs. Identification of the compound was based on mass spectral (MS) evidence including MS/MS data. The concentrations of methyl triclosan in the fish were up to 35 ng g-1 on a wet weight basis and up to 365 ng g -1 on a lipid basis with concentrations in a relatively narrow range for fish from the same lake (Thunersee, 4-6 ng g-1 Zuerichsee, 32-62 ng g-1; Pfaeffikersee, 43-56 ng g-1; Greifensee, 165-365 ng g-1, lipid basis). No methyl triclosan (-1, lipid basis) was detected in fish (lake trout, salmo trutta) from a remote lake in Sweden (Haebberstjaernen) and in fish (roach) from a small lake in Switzerland with no input from WWTPs (Huettnersee, -1, lipid basis). The concentrations of methyl triclosan in fish correlated (r2 = 0.85) with the ratio of population in the watershed to water throughflow of the lakes (P/Q ratio), which is considered to be a measure for the domestic burden from WWTPs to a lake. Passive sampling with SPMDs confirmed the presence of methyl triclosan in lakes and a river (Zuerichsee and Greifensee; Limmat) but not in a remote mountain lake (Joerisee) and in Huettnersee. The bioconcentration factor (BCF) of methyl triclosan estimated from the fish data and SPMD-derived water concentrations was in the order of 1-2.6 × 105 (lipid basis) and thus in the range of other persistent organic pollutants. SPMDs were found to be reliable for monitoring low concentrations of methyl triclosan in surface water. Methyl triclosan appears to be a suitable marker for WWTP-derived lipophilic contaminants in the aquatic environment and fish.

Novel diaryl ureas with efficacy in a mouse model of malaria

Exploration of triclosan analogs has led to novel diaryl ureas with significant potency against in vitro cultures of drug-resistant and drug-sensitive strains of the human malaria parasite Plasmodium falciparum. Compound 18 demonstrated EC50 values of 37 and 55 nM versus in vitro cultured parasite strains and promising in vivo efficacy in a Plasmodium berghei antimalarial mouse model, with >50% survival at day 31 post-treatment when administered subcutaneously at 256 mg/kg. This series of compounds provides a chemical scaffold of novel architecture, as validated by cheminformatics analysis, to pursue antimalarial drug discovery efforts.

Process for the production of 2,4,4'-trichloro-2'-methoxydiphenyl ether

A process is disclosed for the synthesis of 2,4,4'-trichloro-2'-methoxydiphenyl ether, and it's precursor 2,4,4'-trichloro-2'-bromodiphenyl ether, a novel compound.