5-(difluoromethoxy)-1H-benzimidazole-2-thiol

Base Information

• Chemical Name: 5-(difluoromethoxy)-1H-benzimidazole-2-thiol
• CAS No.: 97963-62-7
• Molecular Formula: C8H6F2N2OS
• Molecular Weight: 216.211
• Hs Code.: 29339900
• European Community (EC) Number: 619-308-7
• UNII: 39P59C89NV
• DSSTox Substance ID: DTXSID80243352
• Nikkaji Number: J2.525.436H
• Wikidata: Q27256918
• Mol file: 97963-62-7.mol

Synonyms:97963-62-7;5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole;5-(Difluoromethoxy)-1H-benzo[d]imidazole-2-thiol;5-(difluoromethoxy)-1H-benzimidazole-2-thiol;5-DIFLUOROMETHOXY-2-MERCAPTO-1H-BENZIMIDAZOLE;5-difluoromethoxy-2-mercaptobenzimidazole;5-(difluoromethoxy)-1,3-dihydrobenzimidazole-2-thione;2-Mercapto-5-difluoromethoxy benzimidazole;5-(Difluoromethoxy)-2-mercaptobenzimidazole;SKA-47;2H-Benzimidazole-2-thione, 5-(difluoromethoxy)-1,3-dihydro-;5-(difluoromethoxy)-1H-1,3-benzodiazole-2-thiol;2-Mercapto-5-difluoromethoxy-1H-benzimidazole;5-difluormethoxy-2-mercaepto-1h-benzimidazole;39P59C89NV;MFCD00467504;5-(Difluoromethoxy)-2-benzimidazolethiol;5-Difluoromethoxy-2-thio-benzimidazole;UNII-39P59C89NV;SCHEMBL482378;5-(difluoromethoxy)-1,3-dihydro-2H-benzimidazole-2-thione;DTXSID80243352;Pantoprazole sodium sesquihydrate specified impurity C [EP];AMY16522;AKOS005174324;AKOS028108766;AC-8364;CS-W021039;HY-W040299;PS-6955;5-difluoromethoxy-1H-benzimidazole-2-thiol;5-difluoromethoxy-1H-benzoimidazole-2-thiol;D3438;FT-0620359;FT-0659956;NS00004211;F11378;EN300-1387183;A845773;AG-996/31082058;W-204166;Q27256918;5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole, 97%;Z1269161250;5-(Difluoromethoxy)-1,3-dihydro-2H-benzo[d]imidazole-2-thione;5-(difluoromethoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione;5-[bis(fluoranyl)methoxy]-1,3-dihydrobenzimidazole-2-thione;PANTOPRAZOLE SODIUM SESQUIHYDRATE IMPURITY C [EP IMPURITY]

Chemical Property of 5-(difluoromethoxy)-1H-benzimidazole-2-thiol

Chemical Property:

• Appearance/Colour: Pale Yellow Solid
• Vapor Pressure: 0.000928mmHg at 25°C
• Melting Point: 239-243 °C(lit.)
• Refractive Index: 1.63
• Boiling Point: 303.5 °C at 760 mmHg
• PKA: 9.77±0.30(Predicted)
• Flash Point: 137.3 °C
• PSA: 76.71000
• Density: 1.52 g/cm³
• LogP: 2.45300
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 216.01689032
• Heavy Atom Count: 14
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1OC(F)F)NC(=S)N2
• Uses: Pantoprazole EP Impurity C. Pantoprazole USP Related Compound C.

Technology Process of 5-(difluoromethoxy)-1H-benzimidazole-2-thiol

There total 8 articles about 5-(difluoromethoxy)-1H-benzimidazole-2-thiol 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: 95.4%

carbon disulfide (75-15-0,12122-00-8) + 4-(difluoromethoxy)benzene-1,2-diamine (172282-50-7) → 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7)

Guidance literature:

4-(difluoromethoxy)benzene-1,2-diamine; With sodium carbonate; In water; for 0.333333h; Reflux; Green chemistry;

carbon disulfide; In water; at 25 - 70 ℃; for 12h; Temperature; Reagent/catalyst; Green chemistry;

Reference yield:

3,4-dinitophenol (577-71-9) → 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

2: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C

3: sodium carbonate / water / 12 h / 20 - 70 °C

With palladium 10% on activated carbon; hydrogen; sodium carbonate; caesium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/adsc.201800824

Reference yield:

4-(difluoromethoxy)-1,2-dinitrobenzene → 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C

2: sodium carbonate / water / 12 h / 20 - 70 °C

With palladium 10% on activated carbon; hydrogen; sodium carbonate; In methanol; water;

DOI:10.1002/adsc.201800824

upstream raw materials:

carbon disulfide

4-(difluoromethoxy)benzene-1,2-diamine

3,4-dinitophenol

4-acetaminophenol

Downstream raw materials:

5-(difluoromethoxy)-2-[[(3,4-dimethoxypyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole

5-(difluoromethoxy)-2-(phenylsulfanyl)-1H-benzimidazole

5-(difluoromethoxy)-2-[(4-methylphenyl)sulfanyl]-1H-benzimidazole

5-(difluoromethoxy)-2-[(4-iodophenyl)sulfanyl]-1H-benzimidazole

Refernces

• 1、 Sana, Sravani,Reddy, Velma Ganga,Srinivasa Reddy,Tokala, Ramya,Kumar, Rahul,Bhargava, Suresh K.,Shankaraiah, Nagula. "Cinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies". . . Retrieved 2021/03/15.
• 2、 Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan. "Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation". supporting information. p. 4161 - 4167. Retrieved 2018/09/21.