5-Hydroxy-1,3-dihydrobenzimidazole-2-thione

Base Information

• Chemical Name: 5-Hydroxy-1,3-dihydrobenzimidazole-2-thione
• CAS No.: 92806-98-9
• Molecular Formula: C₇H₆N₂OS
• Molecular Weight: 166.203
• DSSTox Substance ID: DTXSID80562318
• Wikidata: Q82446417
• Mol file: 92806-98-9.mol

Synonyms:92806-98-9;5-hydroxy-1,3-dihydrobenzimidazole-2-thione;2-Mercapto-1H-benzo[d]imidazol-5-ol;6-HYDROXY-2-MERCAPTOBENZIMIDAZOLE;5-HYDROXY-2-MERCAPTO-BENZIMIDAZOLE;2H-Benzimidazole-2-thione, 1,3-dihydro-5-hydroxy-;SCHEMBL7718077;SCHEMBL9213371;SCHEMBL16198465;DTXSID80562318;MFCD04117895;AKOS006295691;AKOS023410873;2-sulfanyl-1H-1,3-benzodiazol-6-ol;AS-61725;CS-0040540;2-MERCAPTO-1H-BENZO[D]IMIDAZOL-6-OL;2-SULFANYL-1H-1,3-BENZODIAZOL-5-OL;W18405;5-Hydroxy-1,3-dihydro-2H-benzimidazole-2-thione;5-hydroxy-2,3-dihydro-1H-1,3-benzodiazole-2-thione;F2167-9515

Chemical Property of 5-Hydroxy-1,3-dihydrobenzimidazole-2-thione

Chemical Property:

• Vapor Pressure: 1E-07mmHg at 25°C
• Melting Point: 287-290 °C(Solv: acetone (67-64-1))
• Refractive Index: 1.831
• Boiling Point: 422.2°C at 760 mmHg
• PKA: 9.97±0.20(Predicted)
• Flash Point: 209.1°C
• PSA: 87.71000
• Density: 1.565g/cm³
• LogP: 1.55720
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 166.02008399
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

5-HYDROXY-2-MERCAPTO-BENZIMIDAZOLE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)NC(=S)N2
• Uses: A metabolite of leminoprazole, a new proton pump inhibitor with potent cytoprotective effect on the gastric mucosa

Technology Process of 5-Hydroxy-1,3-dihydrobenzimidazole-2-thione

There total 3 articles about 5-Hydroxy-1,3-dihydrobenzimidazole-2-thione 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:

5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione (37052-78-1) → 5-hydroxy-2,3-dihydro-1H-1,3-benzodiazole-2-thione (92806-98-9)

Guidance literature:

With pyridine hydrochloride; at 180 ℃; Sealed tube; Inert atmosphere;

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + 3,4-diaminophenol (615-72-5) → 5-hydroxy-2,3-dihydro-1H-1,3-benzodiazole-2-thione (92806-98-9)

Guidance literature:

With potassium hydroxide; In water; at 70 ℃;

DOI:10.1021/acs.jmedchem.7b00587

Reference yield:

4-hydroxy-2-nitroaniline (610-81-1) → 5-hydroxy-2,3-dihydro-1H-1,3-benzodiazole-2-thione (92806-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C

2: potassium hydroxide / water / 70 °C

With palladium 10% on activated carbon; hydrogen; potassium hydroxide; In methanol; water;

DOI:10.1021/acs.jmedchem.7b00587

upstream raw materials:

5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione

carbon disulfide

3,4-diaminophenol

4-hydroxy-2-nitroaniline

Refernces

• 1、 -. "COMPOUNDS USEFUL AS ANTIBIOTIC TOLERANCE INHIBITORS". Page/Page column 44. . Retrieved 2014/11/13.