313485-93-7

Basic information

• Product Name: 6-fluoro-N-phenyl-1H-benzo[d]imidazol-1-amine
• Synonyms: 6-fluoro-N-phenyl-1H-benzo[d]imidazol-1-amine
• CAS NO: 313485-93-7
• Molecular Weight: 227.241
• Mol File: 313485-93-7.mol

Chemical Properties

• CAS DataBase Reference: 6-fluoro-N-phenyl-1H-benzo[d]imidazol-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-fluoro-N-phenyl-1H-benzo[d]imidazol-1-amine(313485-93-7)
• EPA Substance Registry System: 6-fluoro-N-phenyl-1H-benzo[d]imidazol-1-amine(313485-93-7)

Safety Data

• Hazardous Substances Data: 313485-93-7(Hazardous Substances Data)

Upstream product

• 586-96-9 Nitrosobenzene 
• 62-53-3 aniline 
• 67-68-5 dimethyl sulfoxide 
• 313485-92-6 4-fluoro-2-phenylazoaniline 
• 313485-91-5 4-fluoro-2-phenylazoacetanilide 
• 22380-13-8 N-acetyl-2-amino-4-fluoroaniline 
• 50-00-0 formaldehyd 

Relevant articles and documents

Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine

A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “[dbnd]CH[sbnd]” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

Syntheses and properties of 1-methyl-3-phenylaminobenzimidazolium salts, models of DNA adducts of N7-arylaminodeoxyguanosinium salt

When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Heating compound 7 at 80 °C for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N1-formyl-N1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazoles, the 3-phenylamino derivative was found to be more reactive.