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

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

Used in Pharmaceutical Industry:
1,2-Benzenediamine, 4-chloro-5-(2,3-dichlorophenoxy)is used as 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). Triclabendazole is the only anthelmintic drug that is effective against all life stages of flukes, including immature, mature, and adult stages. The compound plays a vital role in the development of treatments for parasitic infections caused by flukes.

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

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

Downstream Products

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

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-ni-trophenyl)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-1,2-diamine of; cyclising 4-chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine in presence of carbondisulfide to obtain 6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol; methylating 6-chloro-5-(2,3-dichlorophenoxy)-1H-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.

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.

Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives (1ae1i) were synthesized via Phillips cyclocondensation of a substituted 1,2-phenylenediamine and trifluoroacetic acid. The synthesized compounds were evaluated in vitro against various protozoan parasites: Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis and Leishmania mexicana, and they showed nanomolar activities against the first three protozoa tested. The compounds were also tested in vitro and in vivo against the nematode Trichinella spiralis. Compounds 1b, 1c and 1e had the most desirable in vitro antiparasitic profile against all parasites studied. In the in vivo model against T. spiralis, compounds 1b and 1e showed good activity against the adult phase at 75 mg/Kg. However, against the muscle larvae stage, only compound 1f exhibited in vivo antiparasitic efficacy.

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).

SYNTHESIS AND REACTIONS OF 2H-BENZIMIDAZOLE-2-SPIROCYCLOHEXANES : AN APPLICATION OF "UMPOLING"

The title compounds are available through condensation of an o-phenylenediamine with cyclohexanone followed by oxidation of the resulting product with manganese dioxide.In this article we review their oxidation, reduction, and rearrangement reactions along with their reactions with nitrogen, oxygen, sulphur, and other nucleophiles.As well as the parent compound the reactions of the 5-chloro-, 5,6-dichloro-, 4,6-dibromo-, 5-phenylsulphonyl- and 5-methoxy-derivative are discussed in some detail.Some applications of the methodology developed, particularly to the synthesis of actual or potential benzimidazole anthelminthics, are given also.