4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine

Base Information

• Chemical Name: 4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine
• CAS No.: 139369-42-9
• Molecular Formula: C12H9Cl3N2O
• Molecular Weight: 303.575
• Hs Code.: 2922299090
• DSSTox Substance ID: DTXSID20433533
• Wikidata: Q82247698
• Mol file: 139369-42-9.mol

Synonyms:139369-42-9;4-chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine;1,2-Benzenediamine, 4-chloro-5-(2,3-dichlorophenoxy)-;SCHEMBL8515928;1,2-Benzenediamine,4-chloro-5-(2,3-dichlorophenoxy)-;DTXSID20433533;AKOS015912328;AC-20361;FT-0709925;A902082;4-chloro-5(2,3-dichlorophenoxy)-1,2-phenylenediamine;4-chloro-5-(2,3-dichlorophenoxy)-1,2-benzenediamine;4-chloro-5-(2,3-dichlorophenoxyl)benzene-1,2-diamine

Chemical Property of 4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.681
• Boiling Point: 419.176 °C at 760 mmHg
• PKA: 3.16±0.10(Predicted)
• Flash Point: 207.31 °C
• PSA: 61.27000
• Density: 1.515 g/cm³
• LogP: 5.76590
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 301.978046
• Heavy Atom Count: 18
• Complexity: 282

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-5-(2,3-dichlorophenoxy)-1,2-benzenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)OC2=C(C=C(C(=C2)N)N)Cl
• 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.

Technology Process of 4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine

There total 9 articles about 4-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline → 4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine (139369-42-9)

Guidance literature:

With sodium tetrahydroborate; palladium 10% on activated carbon; In toluene; for 2h; Reflux;

Reference yield: 89.0%

5-chloro-6-(2,3-dichlorophenoxy)-2H-benzimidazole-2-spirocyclohexane (145770-86-1) → 4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine (139369-42-9)

Guidance literature:

With sodium dithionite; In ethanol; Heating;

Reference yield:

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline (118353-04-1) → 4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine (139369-42-9)

Guidance literature:

With hydrogen; In ethanol; at 25 ℃;

DOI:10.1016/j.ejmech.2010.03.050

upstream raw materials:

5-chloro-6-(2,3-dichlorophenoxy)-2H-benzimidazole-2-spirocyclohexane

sodium 2,3-dichlorophenoxide

5,6-dichloro-2H-benzimidazole-2-spirocyclohexane

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Downstream raw materials:

5-chloro-6-(2,3-dichlorophenoxy)-2-methoxycarbonylamino-1H-benzimidazole

6-chloro-5-(2,3-dichlorophenoxy)-2-(trifluoromethyl)-1H-benzimidazole

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole hydrochloride

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF TRICLABENDAZOLE". Paragraph 0025. . Retrieved 2013/11/19.
• 2、 Hernández-Luis, Francisco,Hernández-Campos, Alicia,Castillo, Rafael,Navarrete-Vázquez, Gabriel,Soria-Arteche, Olivia,Hernández-Hernández, Manuel,Yépez-Mulia, Lilián. "Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis". experimental part. p. 3135 - 3141. Retrieved 2010/09/03.