5-Chloro-1H-benzimidazole

Base Information

• Chemical Name: 5-Chloro-1H-benzimidazole
• CAS No.: 4887-82-5
• Molecular Formula: C7H5ClN2
• Molecular Weight: 152.583
• Hs Code.: 2933990090
• European Community (EC) Number: 225-503-4
• NSC Number: 3059
• DSSTox Substance ID: DTXSID20197623
• Nikkaji Number: J208.176H
• Wikidata: Q27460054
• ChEMBL ID: CHEMBL69098
• Mol file: 4887-82-5.mol

Synonyms:5-Chlorobenzimidazole;4887-82-5;5-Chloro-1H-benzimidazole;6-chloro-1H-benzo[d]imidazole;6-chloro-1H-benzimidazole;5-chloro-1H-benzo[d]imidazole;1H-Benzimidazole, 5-chloro-;MFCD00059698;CHEMBL69098;EINECS 225-503-4;5-chloro-1H-1,3-benzodiazole;3kqw;NSC3059;5-Chloro-1H-benzoimidazole;6-Chloro-1 h-benzimidazole;5-Chlorobenzimidazole, 96%;5-Chloro-1H-benzimidazole #;SCHEMBL1445052;6-chloro-1H-1,3-benzodiazole;DTXSID20197623;AMY10738;NSC 3059;NSC-3059;BDBM50404928;STL388902;AKOS000297100;AKOS000298837;MB04649;NCGC00184566-01;NCGC00184566-02;NCGC00184566-03;NCGC00184566-04;DS-10121;SY050745;CS-0035816;FT-0620309;A18809;W-202867;Q27460054;ES9

Chemical Property of 5-Chloro-1H-benzimidazole

Chemical Property:

• Melting Point: 118-122 °C(lit.)
• Boiling Point: 393.8 °C at 760 mmHg
• PKA: 11.23±0.30(Predicted)
• Flash Point: 224.2 °C
• PSA: 28.68000
• Density: 1.425 g/cm³
• LogP: 2.21630
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Practically insoluble in water
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.0141259
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

98% ^*data from raw suppliers

6-Chloro-1h-benzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-41
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)NC=N2

Technology Process of 5-Chloro-1H-benzimidazole

There total 36 articles about 5-Chloro-1H-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%

formic acid (64-18-6) + 4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-1H-benzimidazole (4887-82-5)

Guidance literature:

With hydrogenchloride; In water; for 3h; Reflux;

DOI:10.3390/molecules200815206

Reference yield: 95.0%

4-Chloro-1,2-phenylenediamine (95-83-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-chloro-1H-benzimidazole (4887-82-5)

Guidance literature:

With hydrogenchloride; In water; at 150 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.1039/c5ra00021a

Reference yield: 95.0%

4-Chloro-1,2-phenylenediamine (95-83-0) + orthoformic acid triethyl ester (122-51-0) → 5-chloro-1H-benzimidazole (4887-82-5)

Guidance literature:

With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate; at 45 - 46 ℃; for 0.166667h; Ionic liquid; Sonication; neat (no solvent);

DOI:10.1002/ejoc.201100128

upstream raw materials:

formic acid

4-Chloro-1,2-phenylenediamine

Vilsmeier reagent

6-chloro-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one

Downstream raw materials:

1-methyl-6-chloro-1H-benzo[d]imidazole

1-methyl-5-chlorobenzimidazole

2-(3-cyano-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-(5-chloro-benzoimidazol-1-yl)-2-fluoro-phenyl]-amide

2-(3-cyano-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-(6-chloro-benzoimidazol-1-yl)-2-fluoro-phenyl]-amide

Refernces

• 1、 An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong. "Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles". supporting information. p. 748 - 753. Retrieved 2022/02/02.
• 2、 -. "Method for synthesizing benzimidazole from carbon dioxide and o-phenylenediamine compound". Paragraph 0029-0032. . Retrieved 2021/06/06.