10173-54-3

Usage

Chemical class

Benzenamines

Molecular weight

237.3 g/mol

Physical appearance

Yellow to brown crystalline solid

Solubility

Sparingly soluble in water, soluble in organic solvents like ethanol and ether

Uses

Building block in the synthesis of pharmaceutical products and organic compounds, precursor in the synthesis of dyes, pigments, and pharmaceuticals, used in research laboratories for its unique structural and chemical properties.

Upstream product

• 118-48-9 isatoic anhydride 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 134662-91-2 [1-(4,5-Dimethoxy-2-nitro-phenyl)-meth-(E)-ylidene]-[2-(5,6-dimethyl-1H-benzoimidazol-2-yl)-phenyl]-amine 
• 134662-78-5 6-(4,5-Dimethoxy-2-nitro-phenyl)-9,10-dimethyl-5,6-dihydro-benzo[4,5]imidazo[1,2-c]quinazoline 
• 134662-90-1 [2-(5,6-Dimethyl-1H-benzoimidazol-2-yl)-phenyl]-[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amine 
• 134662-77-4 9,10-Dimethyl-6-(2-nitro-phenyl)-5,6-dihydro-benzo[4,5]imidazo[1,2-c]quinazoline 
• 865203-22-1 2-[2-(benzylamino)phenyl]-5,6-dimethylbenzimidazole 
• 939295-17-7 C₂₄H₂₃N₃O 
• 939321-95-6 C₂₃H₂₁N₃ 
• 932022-78-1 C₂₂H₁₈N₄O₂ 
• 932022-76-9 C₂₂H₁₈ClN₃ 
• 939346-82-4 C₂₅H₂₅N₃O₃ 
• 939321-87-6 C₂₄H₂₃N₃O₂ 
• 932022-79-2 6-(4-methoxyphenyl)-9,10-dimethyl-5,6-dihydrobenzo[4,5]imidazo[1,2-c]quinazoline 
• 939671-14-4 C₂₄H₂₄N₄ 
• 932022-75-8 9,10-dimethyl-5,6-dihydrobenzoimidazo[1,2-c]quinazoline 

Relevant academic research and scientific papers

Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via a Sequential Double Annulation Cascade (SDAC) Strategy

An efficient protocol for the synthesis of quinazoline derivatives through nickel-catalyzed ligand-/base-free oxidative isocyanide insertion under aerobic conditions with intramolecular bis-amine nucleophiles has been developed. A one-pot sequential double annulation cascade (SDAC) strategy involving an opening of isatoic anhydride and annulation to benzimidazole and further nickel-catalyzed intramolecular isocyanide insertion has also been demonstrated. The method is operationally simple to implement with a wide variety of substrates and represents a new approach for multiple C-N bond formations. The methodology has been successfully applied to the syntheses of hitherto unreported imidazo-fused benzimidazoquinazolines via a deprotection-GBB reaction sequence. Further, a florescence study reveals the potential of the present strategy for the discovery of highly fluorescent probes.

Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives

An efficient, green, and novel method for the synthesis of N-heterocycle-fused quinoxalines is reported herein. Dimethyl sulfoxide was used as both a reactant and a solvent in this reaction. A wide range of products in moderate to excellent yields were obtained, including pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, 1H-pyrrolo[3,2-c]quinolines, and benzo[4,5]imidazo[1,2-c]quinazolines.

Combined Pd/C and montmorillonite catalysis for one-pot synthesis of benzimidazoles

A series of nineteen benzimidazoles were prepared from ortho-nitroanilines by one-pot transfer hydrogenation, condensation, and dehydrogenation enabled by the concurrent use of two heterogeneous catalysts: montmorillonite-K10 and Pd/C. This strategy was further employed to accomplish a five-step, three-component synthesis of an antifungal benzimidazoquinazoline by using a simple one-pot procedure.

Efficient method for the synthesis of benzimidazoquinazoline derivatives with three-point diversity

An efficient strategy for the preparation of a novel heterocyclic ring system of benzimidazoquinazolines with three-point diversity has been described. The compounds were obtained by treating o-phenylene diamines with o-nitrobenzaldehyde to give benzimidazoles, followed by reduction of the nitro group to give an amine. Derivatization of the resulting amine with isothiocyanates followed by in situ cyclodesulfurization at rt furnished the title compounds in high yields and purities. Copyright Taylor & Francis Group, LLC.