Benzimidazole

Base Information

• Chemical Name: Benzimidazole
• CAS No.: 51-17-2
• Deprecated CAS: 116421-27-3,25463-25-6,79351-71-6,25463-25-6,79351-71-6
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 29339990
• European Community (EC) Number: 200-081-4
• NSC Number: 759
• UNII: E24GX49LD8
• DSSTox Substance ID: DTXSID8024573
• Nikkaji Number: J2.303E
• Wikipedia: Benzimidazole
• Wikidata: Q415190
• Metabolomics Workbench ID: 52280
• ChEMBL ID: CHEMBL306226
• Mol file: 51-17-2.mol

Synonyms:benzimidazole;benzimidazole monohydrochloride;benzimidazole mononitrate

Chemical Property of Benzimidazole

Chemical Property:

• Appearance/Colour: white crystal
• Melting Point: 169-171 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 360 °C at 760 mmHg
• PKA: 5.532(at 25℃)
• Flash Point: 208.439 °C
• PSA: 28.68000
• Density: 1.242 g/cm³
• LogP: 1.56290
• Storage Temp.: Store below +30°C.
• Solubility.: xylene: soluble1g in 2g (boiling)(lit.)
• Water Solubility.: sparingly soluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

Benzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1=CC=C2C(=C1)NC=N2
• Recent ClinicalTrials: Alveolar Echinococcosis: Parasite Viability and Innovative Markers for the Follow-up of Patients Treated With Albendazole
• Uses: Usually used as template compound in the preparation of molecularly imprinted polymer via electropolymerization and electrodeposition of pyrrole on a pencil graphite electrode,and also used in the preparation of benzimidazolium surfactant, 1-hexadecyl-1H-benzimidazole. Benzimidazole is a building block for making anthelmintic drugs like albendazole, mebendazole and triclabendazole and anti-ulcer drugs like pantoprazole, rabeprazole, lansoprazole and omeprazole. It is used in the preparation of pyrene derived benzimidazole linked polymers (BILPs), which are used for selective carbon dioxide separation applications due to their properties like porous materials, regenerability and sorbent selection parameters.

Technology Process of Benzimidazole

There total 291 articles about 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%

3-amino-3-(o-aminoanilino)-2-cyano-2-propenal phenylhydrazone (106157-75-9) → benzoimidazole (51-17-2,79351-71-6) + 5-Amino-4-cyano-1-phenylpyrazole (5334-43-0)

Guidance literature:

With orthoformic acid triethyl ester; In butan-1-ol; for 4h; Heating;

Reference yield: 100.0%

3-amino-3-(o-aminoanilino)-2-cyano-2-propenal phenylhydrazone (106157-75-9) + orthoformic acid triethyl ester (122-51-0) → benzoimidazole (51-17-2,79351-71-6) + 5-Amino-4-cyano-1-phenylpyrazole (5334-43-0)

Guidance literature:

In butan-1-ol; for 4h; Heating;

Reference yield: 99.0%

carbon dioxide (124-38-9,18923-20-1) + 1,2-diamino-benzene (95-54-5) → benzoimidazole (51-17-2,79351-71-6)

Guidance literature:

With diphenylsilane; C₃₃H₃₆BO₆^(3-)*Eu⁽³⁺⁾*H₂O*2C₃H₇NO; In acetonitrile; at 120 ℃; for 24h; under 7500.75 Torr; Reagent/catalyst; Temperature; Solvent; Time; Catalytic behavior; Autoclave;

DOI:10.1002/anie.201901171

upstream raw materials:

1,3,5-Triazine

1,2-diamino-benzene

2-benzimidazolecarboxylic acid

chloroform

Downstream raw materials:

benzoimidazole-1-carboxylic acid anilide

1-Piperidinomethyl-benzimidazol

N-benzoylbenzimidazole

N,N'-(1,2-phenylene)dibutyramide

Refernces

• 1、 Zhang, Shu Hua,Zhao, Ru Xia,Li, Gui,Zhang, Hai Yang,Li, He Ping. "Synthesis, Structure, and Luminescent Property of One Zinc(II) Coordination Polymer Constructed from 1H-Benzoimidazole". . p. 804 - 808. Retrieved 2016.
• 2、 Klosa. "-". . p. 62. Retrieved 1954.
• 3、 Guseinov,Yudina,Burangulova,Ryzhikova,Valiullina. "Heterocyclization of ethyl esters of 2-chloro-3-substituted aminoacrylic acids with o-phenylenediamine [4]". . p. 496 - 497. Retrieved 2002.
• 4、 Guseinov,Asadov,Burangulova,Moskva. "2-Dialkoxyphosphoryl-1,4-dihydrobenzodiazines [4]". . p. 1044 - 1045. Retrieved 2001.
• 5、 Laha, Joydev K.,Gupta, Pankaj. "Sulfoxylate Anion Radical-Induced Aryl Radical Generation and Intramolecular Arylation for the Synthesis of Biarylsultams". supporting information. p. 4204 - 4214. Retrieved 2022/03/16.
• 6、 Li, Hu,Li, Zhengyi,Wu, Hongguo,Yang, Song,Yu, Zhaozhuo,Zhang, Lilong,Zhu, Kaixun. "A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles". supporting information. p. 5759 - 5765. Retrieved 2021/08/23.