2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

Base Information

• Chemical Name: 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol
• CAS No.: 41433-12-9
• Molecular Formula: C13H9ClN2O
• Molecular Weight: 244.68
• DSSTox Substance ID: DTXSID20421132
• Nikkaji Number: J683.484A
• Wikidata: Q82232507
• ChEMBL ID: CHEMBL4091270
• Mol file: 41433-12-9.mol

Synonyms:2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol;41433-12-9;2-(1H-Benzimidazol-2-yl)-4-chlorophenol;SCHEMBL7396100;CHEMBL4091270;DTXSID20421132;PBENZIMZQAFNCZ-UHFFFAOYSA-N;AKOS005824988;FT-0743014

Chemical Property of 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

Chemical Property:

• PSA: 48.65000
• LogP: 2.18940
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 244.0403406
• Heavy Atom Count: 17
• Complexity: 276

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)NC(=N2)C3=C(C=CC(=C3)Cl)O

Technology Process of 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

There total 13 articles about 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol 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: 90.0%

1,2-diamino-benzene (95-54-5) + 5-chlorosalicyclaldehyde (635-93-8) → 2-(2'-Hydroxy-5'-chlorophenyl)benzimidazole (41433-12-9)

Guidance literature:

With sodium metabisulfite; In N,N-dimethyl-formamide; at 80 ℃; for 0.2h; Microwave irradiation;

DOI:10.1002/jhet.1058

Reference yield: 27.0%

5-chloro-2-methoxybenzoic acid (3438-16-2) + 1,2-diamino-benzene (95-54-5) → 2-(2'-Hydroxy-5'-chlorophenyl)benzimidazole (41433-12-9)

Guidance literature:

5-chloro-2-methoxybenzoic acid; 1,2-diamino-benzene; With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; at 200 ℃; for 5h;

With potassium hydroxide; In water; Cooling with ice;

Reference yield: 20.0%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 1,2-diamino-benzene (95-54-5) → 2-(2'-Hydroxy-5'-chlorophenyl)benzimidazole (41433-12-9)

Guidance literature:

With PPA; at 150 ℃;

DOI:10.1021/jo00122a027

upstream raw materials:

N,N'-bis(5-chlorosalicylidene)-1,2-phenylenediamine

Methyl-carbamic acid 4-chloro-2-((E)-2-nitro-vinyl)-phenyl ester

1,2-diamino-benzene

5-chlorosalicyclaldehyde

Downstream raw materials:

5-(6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Refernces

• 1、 Das, Suven,Maity, Suvendu,Ghosh, Prasanta,Dutta, Arpita. "The ninhydrin core as carbonyl source to access 2-(2′-hydroxyaryl)benzimidazoles exploiting the ortho selectivity of ninhydrin-phenol adducts". . p. 2862 - 2872. Retrieved 2021/08/13.
• 2、 Samanta, Partha Kumar,Banerjee, Rumeli,Richards, Ryan M.,Biswas, Papu. "Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles". . . Retrieved 2018/08/06.