2-(4-Chlorophenyl)benzimidazole

Base Information

• Chemical Name: 2-(4-Chlorophenyl)benzimidazole
• CAS No.: 1019-85-8
• Molecular Formula: C13H9 Cl N2
• Molecular Weight: 228.681
• DSSTox Substance ID: DTXSID90353951
• Nikkaji Number: J570.082E
• Wikidata: Q82131828
• ChEMBL ID: CHEMBL473163
• Mol file: 1019-85-8.mol

Synonyms:2-(4-Chlorophenyl)benzimidazole;1019-85-8;2-(4-chlorophenyl)-1H-benzimidazole;2-(4-chlorophenyl)-1H-benzo[d]imidazole;2-(4-Chlorophenyl)-1H-benzoimidazole;1H-Benzimidazole, 2-(4-chlorophenyl)-;2-(4-CHLOROPHENYL)-1H-1,3-BENZODIAZOLE;2-(4-Chloro-phenyl)-1H-benzoimidazole;SCHEMBL197619;CHEMBL473163;DTXSID90353951;PTXUJRTVWRYYTE-UHFFFAOYSA-N;CCG-15108;MFCD00224359;STL290574;AKOS000275582;AS-63173;BB 0219544;C2027;CS-0095531;EU-0033463;SR-01000389454;SR-01000389454-1;Z50129862

Chemical Property of 2-(4-Chlorophenyl)benzimidazole

Chemical Property:

• Vapor Pressure: 3.13E-07mmHg at 25°C
• Melting Point: 303 °C
• Boiling Point: 419°C at 760 mmHg
• PKA: 11.24±0.10(Predicted)
• Flash Point: 239.7°C
• PSA: 28.68000
• Density: 1.326g/cm³
• LogP: 3.88330
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 228.0454260
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

98% ^*data from raw suppliers

2-(4-Chlorophenyl)-1H-benzo[d]imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)NC(=N2)C3=CC=C(C=C3)Cl
• Uses: 2-(4-Chlorophenyl)-1H-benzo[d]imidazole has been used as a reactant in the synthesis of benzylsulfanyl((phenylbenzimidazolyl)methyl)oxadiazoles with antioxidant activity.

Technology Process of 2-(4-Chlorophenyl)benzimidazole

There total 136 articles about 2-(4-Chlorophenyl)benzimidazole 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: 100.0%

4-chlorobenzaldehyde (104-88-1) + 1,2-diamino-benzene (95-54-5) → 2-(4-chlorophenyl)benzimidazole (1019-85-8)

Guidance literature:

With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 100 ℃; for 2h;

DOI:10.1080/00397910902730838

Reference yield: 98.0%

1,2-diamino-benzene (95-54-5) + para-Chlorobenzyl alcohol (873-76-7) → 2-(4-chlorophenyl)benzimidazole (1019-85-8)

Guidance literature:

With [RuCl(CO)(PPh₃)(PNS-Me)]; potassium hydroxide; In toluene; at 100 ℃; for 24h; Catalytic behavior;

DOI:10.1039/c4dt00006d

Reference yield: 96.0%

2-nitro-aniline (88-74-4) + para-Chlorobenzyl alcohol (873-76-7) → 2-(4-chlorophenyl)benzimidazole (1019-85-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene; at 160 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2016.09.018

upstream raw materials:

4-Cyanochlorobenzene

o-phenylenediamine hydrochloride

5-(4-chlorophenyl)-1-phenyl-1H-tetrazole

N-(4-chlorobenzyl)-pyridinium bromide

Downstream raw materials:

C₁₉H₁₂ClN₃O

3-chloro-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline

(E)-1-(2-(4-chlorophenyl)-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one

Refernces

• 1、 Yu, Jiatao,Lu, Ming. "[C12mim] Br: A temperature-dependent phase transfer catalyst and its application for aerobic oxidative synthesis of 2-aryl benzimidazoles, benzoxazoles or benzothiozoles catalyzed by TEMPO based ionic liquid". . p. 578 - 582. Retrieved 2014.
• 2、 Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Alaie, Saied,Baghery, Saeed,Maleki, Farahnaz,Bayat, Yadollah,Asgari, Asiye. "Experimental and theoretical approving of anomeric based oxidation in the preparation of 2-sbstituted benz-(imida, oxa and othia)-zoles using [2,6-DMPy-NO2]C(NO2)3 as a novel nano molten salt catalyst". . p. 58667 - 58679. Retrieved 2016.
• 3、 Sayahi, Mohammad Hosein,Khoshneviszadeh, Mehdi,Soheilizad, Mehdi,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad. "Efficient copper-catalyzed synthesis of 2-arylbenzimidazole derivatives by reaction of 1-fluoro-2-nitrobenzene with benzamidine hydrochlorides". . . Retrieved 2018.
• 4、 Xu, Fen,Kang, Wei-Fen,Wang, Xiao-Ning,Kou, Hao-Dong,Jin, Zhen,Liu, Chun-Sen. "Synergic effect of copper-based metal-organic frameworks for highly efficient C-H activation of amidines". . p. 51658 - 51662. Retrieved 2017.
• 5、 Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Moradi, Parisa,Havasi, Nasrin. "Cu–S-(propyl)-2-aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides". . p. 619 - 625. Retrieved 2016.
• 6、 Hajipour, Abdol R.,Zakery, Saedeh,Khorsandi, Zahra. "Synthesis of benzimidazoles by two methods (C–H functionalization and condensation reaction) catalyzed by α-zirconium hydrogen phosphate-based nanocatalyst". . p. 1919 - 1931. Retrieved 2020.
• 7、 Karami, Changiz,Ghodrati, Keivan,Izadi, Mina,Farrokh, Azita,Jafari, Sedigheh,Mahmoudiyani, Maryam,Haghnazari, Nahid. "A fast procedure for the preparation of benzimidazole derivatives using polymer-supported with trifluoromethanesulfonic acid as novel and reusable catalyst". . p. 1914 - 1917. Retrieved 2013.
• 8、 Lin, Chuncheng,Wan, Weihao,Wei, Xueting,Chen, Jinzhu. "H2 Activation with Co Nanoparticles Encapsulated in N-Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles". . p. 709 - 720. Retrieved 2021.
• 9、 Dubey, Raghvendra,Hari Narayana Moorthy, Narayana Subbiah. "Comparative studies on conventional and microwave assisted synthesis of benzimidazole and their 2-substituted derivative with the effect of salt form of reactant". . p. 115 - 117. Retrieved 2007.
• 10、 Du, Li-Hua,Wang, Yan-Guang. "A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant". . p. 675 - 678. Retrieved 2007.