5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-thione

Base Information

• Chemical Name: 5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-thione
• CAS No.: 92807-01-7
• Molecular Formula: C8H8 N2 O S
• Molecular Weight: 180.23
• DSSTox Substance ID: DTXSID401204530
• Mol file: 92807-01-7.mol

Synonyms:92807-01-7;5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-thione;5-hydroxymethyl-2-mercaptobenzoimidazole;SCHEMBL6324712;YQRLUAKDAJJAHH-UHFFFAOYSA-N;DTXSID401204530;5-hydroxymethyl-2-mercaptobenzimidazole;1,3-Dihydro-5-(hydroxymethyl)-2H-benzimidazole-2-thione

Chemical Property of 5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-thione

Chemical Property:

• PSA: 87.71000
• LogP: 1.34390
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 180.03573406
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1CO)NC(=S)N2

Technology Process of 5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-thione

There total 7 articles about 5-(Hydroxymethyl)-1H-benzo[d]imidazole-2(3H)-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:

methyl 2-mercaptobenzimidazole-5-carboxylate (64375-41-3) → 5-hydroxymethyl-2-mercaptobenzoimidazole (92807-01-7)

Guidance literature:

methyl 2-mercaptobenzimidazole-5-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 10 - 20 ℃; for 1h;

With water; In tetrahydrofuran; for 0.166667h;

Reference yield:

methyl 4-acetamidobenzoate (17012-22-5) → 5-(hydroxymethyl)-2-mercapto-1H-benzimidazole (92807-01-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / fuming nitric acid

2: 41 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

3: 9 M HCl / 0.5 h / Heating

4: H₂ / Pd/C / ethanol

5: ethanol; H₂O / 12 h / Heating

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; nitric acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; water;

DOI:10.1021/jm00025a008

Reference yield:

4-(hydroxymethyl)-2-nitroacetanilide (73166-06-0) → 5-(hydroxymethyl)-2-mercapto-1H-benzimidazole (92807-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 9 M HCl / 0.5 h / Heating

2: H₂ / Pd/C / ethanol

3: ethanol; H₂O / 12 h / Heating

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jm00025a008

upstream raw materials:

1,2-diamino-4-hydroxymethylbenzene

potassium ethyl xanthogenate

methyl 4-acetamidobenzoate

4-(hydroxymethyl)-2-nitroacetanilide

Downstream raw materials:

[2-(4-Methoxy-3-methyl-pyridin-2-ylmethylsulfanyl)-1H-benzoimidazol-5-yl]-methanol

5-(t-butyldiphenylsilyloxymethyl)-2-mercaptobenzoimidazole