139369-42-9

Basic information

• Product Name: 1,2-BENZENEDIAMINE, 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-
• Synonyms: 1,2-BENZENEDIAMINE, 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-;4-CHLORO-5-(2,3-DICHLORO-PHENOXY)-1,2-BENZENEDIAMINE;4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diaMine
• CAS NO: 139369-42-9
• Molecular Formula: C₁₂H₉Cl₃N₂O
• Molecular Weight: 303.57
• Mol File: 139369-42-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 419.176 °C at 760 mmHg
• Flash Point: 207.31 °C
• Appearance: /
• Density: 1.515 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.681
• PKA: 3.16±0.10(Predicted)
• CAS DataBase Reference: 1,2-BENZENEDIAMINE, 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZENEDIAMINE, 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-(139369-42-9)
• EPA Substance Registry System: 1,2-BENZENEDIAMINE, 4-CHLORO-5-(2,3-DICHLOROPHENOXY)-(139369-42-9)

Safety Data

• Hazardous Substances Data: 139369-42-9(Hazardous Substances Data)

Usage

Uses

4-Chloro-5-(2,3-dichlorophenoxy)-1,2-benzenediamine is an intermediate in the synthesis of 5-Chloro-6-(2,3-dichlorophenoxy)-1,3-dihydro-2H-benzimidazol-2-one (C365505), which is a metabolite of Triclabendazole (T774175), the only anthelmintic drug, which is active against immature, mature and adult stages of fluke.

InChI:InChI=1/C12H9Cl3N2O/c13-6-2-1-3-10(12(6)15)18-11-5-9(17)8(16)4-7(11)14/h1-5H,16-17H2

Upstream product

• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 5462-30-6 N-(4,5-dichloro-2-nitrophenyl)acetamide 
• 576-24-9 2,3-dichlorophenol 
• 118353-04-1 4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline 
• 117644-38-9 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 
• 95454-60-7 sodium 2,3-dichlorophenoxide 
• 145770-86-1 5-chloro-6-(2,3-dichlorophenoxy)-2H-benzimidazole-2-spirocyclohexane 

Downstream Products

• 145771-00-2 5-chloro-6-(2,3-dichlorophenoxy)-2-(trifluoromethyl)-1H-benzimidazole 
• 145771-00-2 6-chloro-5-(2,3-dichlorophenoxy)-2-(trifluoromethyl)-1H-benzimidazole 
• 68828-69-3 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol 
• 1378851-20-7 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride 
• 68786-66-3 triclabendazole 
• 1473415-03-0 6-chloro-5-(2,3-dichlorophenoxy)-2-heptafluoropropylbenzimidazole 
• 1380167-24-7 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole methylsulfate 
• 68786-66-3 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole 
• 145771-01-3 5-chloro-6-(2,3-dichlorophenoxy)-2-methoxycarbonylamino-1H-benzimidazole 
• 68828-69-3 5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione 

Relevant articles and documents

Method for preparing triclabendazole serving as medicine for animal distomiasis

The invention relates to a method for preparing triclabendazole serving as a medicine for animal distomiasis. 2,3-dichlorophenol and 3,4-dichloro-5-nitroaniline are used as raw materials and subjected to etherification, reduction reaction, cyclization and methylation to obtain triclabendazole. In the step of etherification, high-alkalinity potassium ethoxide or potassium methoxide is adopted for replacement of potassium hydroxide in the prior art while microwave irradiation heating is performed, and consequently step-by-step preparation of potassium phenoxide is avoided, phase transfer catalysts are not required, 'one-step' etherification is realized, etherification yield is up to 96% or above, product purity reaches 98% or above, and demands of industrial application are met.

PROCESS FOR PREPARATION OF TRICLABENDAZOLE

The present invention discloses a method for preparing Triclabendazole comprising condensing N-(4,5-dichloro-2-nitrophenyl)acetamide with 2,3-dichlorophenol to obtain 4-chloro-5(2,3-dichlorophenoxy)-2-nitrophenyl acetamide and it to obtain 4- chloro-5(2,3-dichlorophenoxy)-2-nitroaniline; reducing 4-chloro-5(2,3- dichlorophenoxy)-2-nitroaniline in presence of Raney nickel to obtain 4-chloro-5- (2,3-dichlorophenoxy)benzene-l,2-diamine of; cyclising 4-chloro-5-(2,3- dichlorophenoxy)benzene-l,2-diamine in presence of carbondisulfide to obtain 6- chloro-5-(2,3-dichlorophenoxy)-lH-benzimidazole-2-thiol; methylating 6-chloro-5- (2,3-dichlorophenoxy)-lH-benzimidazole-2 -thiol using a methylating agent to obtain triclabendazole methanesulfonate salt; converting triclabendazole methanesulfonate salt to hydrochloride salt of Triclabendazole and hydrolysing it to obtain Triclabendazole.

2H-Benzimidazoles (Isobenzimidazoles). Part 7. A New Route to Triclabendazole and Congeneric Benzimidazoles

A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described.Analogous benzimidazoles difficult to prepare by conventional methods are similarly obtained.Triclabendazole can exist as a low-melting metastable solid (m.p. 85-90 deg C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 176-178 deg C).