Clemizole

Base Information

• Chemical Name: Clemizole
• CAS No.: 442-52-4
• Molecular Formula: C19H20 Cl N3
• Molecular Weight: 325.841
• Hs Code.: 2933990090
• European Community (EC) Number: 207-133-5
• NSC Number: 46261
• UNII: T97CB3796L
• DSSTox Substance ID: DTXSID0046939
• Nikkaji Number: J5.745B
• Wikipedia: Clemizole
• Wikidata: Q5131527
• NCI Thesaurus Code: C81139
• Pharos Ligand ID: KW3WXVH44N93
• Metabolomics Workbench ID: 58123
• ChEMBL ID: CHEMBL1407943
• Mol file: 442-52-4.mol

Synonyms:clemizole

Chemical Property of Clemizole

Chemical Property:

• Vapor Pressure: 2.29E-10mmHg at 25°C
• Melting Point: 239-241℃
• Boiling Point: 506.1°Cat760mmHg
• Flash Point: 259.9°C
• PSA: 21.06000
• Density: 1.25g/cm³
• LogP: 4.27170
• Solubility.: insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥95.8 mg/mL in EtOH
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 325.1345753
• Heavy Atom Count: 23
• Complexity: 377

Purity/Quality:

98%,99%, ^*data from raw suppliers

Clemizole(freebase) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCN(C1)CC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)Cl
• Therapeutic Function: Antihistaminic

Technology Process of Clemizole

There total 16 articles about Clemizole 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: 88.0%

1-(4-chlorobenzyl)-2-(methylsulfonyl)-1H-benzo[d]imidazole + 1-((trimethylsilyl)methyl)pyrrolidine (54600-29-2) → clemizole (442-52-4)

Guidance literature:

With Eosin Y; In methanol; acetonitrile; at 20 ℃; for 3h; Irradiation;

DOI:10.1002/chem.202102124

Reference yield: 65.0%

4-chlorobenzyl bromide (622-95-7) + 2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole (2948-92-7) → clemizole (442-52-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2014.11.066

Reference yield: 49.0%

pyrrolidine (123-75-1) + 1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole (7189-18-6) → clemizole (442-52-4)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; at 20 ℃; for 16h;

upstream raw materials:

pyrrolidine

chloro-acetic acid-[2-(4-chloro-benzylamino)-anilide]

1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole

pyrrolidino-acetic acid-[2-(4-chloro-benzylidenamino)-anilide]

Downstream raw materials:

clemizole hydrochloride

1-(4-chlorobenzyl)-2-(d2-(pyrrolidin-1-yl)methyl)-1H-benzo[d]imidazole

Refernces

• 1、 Zhang, Xiaohui,Huang, Ruofeng,Marrot, Jér?me,Coeffard, Vincent,Xiong, Yan. "Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement". . p. 700 - 708. Retrieved 2015/02/02.
• 2、 -. "BENZIMIDAZOLE MODULATORS OF H1 RECEPTOR AND/OR NS4B PROTEIN ACTIVITY". Page/Page column 30-31. . Retrieved 2010/11/03.