1772-39-0

Usage

Uses

Used in High-Energy Material Synthesis:
5-nitro-2-(4-nitrophenyl)-1H-benzimidazole is used as a precursor in the synthesis of high-energy materials for its ability to contribute to the energetic properties of the final compounds.
Used in Explosive Stabilization:
In the explosives industry, 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole is used as a stabilizer to enhance the safety and performance of explosive materials.
Used as an Oxidizing Agent in Organic Synthesis:
5-nitro-2-(4-nitrophenyl)-1H-benzimidazole is utilized as an efficient and environmentally friendly oxidizing agent in organic synthesis, facilitating various chemical reactions.
Used in Pharmaceutical Development:
As a building block in pharmaceuticals, 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole is used for the development of new drugs, capitalizing on its chemical structure to create novel medicinal compounds.
Used as a Corrosion Inhibitor in Metal Surface Protection:
5-nitro-2-(4-nitrophenyl)-1H-benzimidazole is applied as a corrosion inhibitor in the metal industry to protect metal surfaces from degradation, extending their lifespan and maintaining their integrity.

InChI:InChI=1/C13H8N4O4/c18-16(19)9-3-1-8(2-4-9)13-14-11-6-5-10(17(20)21)7-12(11)15-13/h1-7H,(H,14,15)

Upstream product

• 729-13-5 2-(4-nitrophenyl)benzimidazole 
• 555-16-8 4-nitrobenzaldehdye 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 39214-83-0 3-(4-nitrophenyl)isoxazol-5(4H)-one 
• 140429-25-0 N-pyridinium chloride 
• 41468-11-5 sodium hydroxy(4-nitrophenyl)methanesulfonate 
• 174414-25-6 (Z)-3-(2-Amino-5-nitro-phenylamino)-1-(4-bromo-phenyl)-3-(4-nitro-phenyl)-propenone 
• 102692-40-0 3-(4-nitrophenyl)-1-p-tolylprop-2-en-1-one 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 71002-88-5 2-(4-aminophenyl)-5⁽⁶⁾-nitrobenzimidazole 
• 7621-86-5 6-amino-2-(4'-aminophenyl)-benzimidazole 
• 106167-15-1 1-methyl-5-nitro-2-(4-nitrophenyl)-1H-benzo[d]imidazole 
• 87353-68-2 N,N'-Bis<2-(4-trifluoroacetamidophenyl)benzimidazol-5-yl>terephthaloyl diamide 
• 87345-65-1 N,N'-Bis<2-(4-aminophenyl)benzimidazol-5-yl>terephthaloyl diamide 
• 87345-59-3 5-Nitro-4'-trifluoroacetamido-2-phenylbenzimidazole 
• 345934-83-0 N-[4-(6-Amino-1H-benzoimidazol-2-yl)-phenyl]-2,2,2-trifluoro-acetamide 
• 7621-86-5 2-(4-aminophenyl)-5-amino-benzimidazole 

Relevant academic research and scientific papers

Reaction of 4-nitro-1,2-phenylenediamine with 1-(4-R-phenyl)-3-(4-nitrophenyl)propenones

By the reaction of 4-nitro-1,2-phenylenediamine with 1-(p-R-phenyl)-3-(4-nitrophenyl)propenones, Michael adducts with a 1:2 composition have been obtained. A stagewise scheme is proposed for the formation of these compounds. The structure of one of the products has been established by means of x-ray structure analysis. 1996 Plenum Publishing Corporation.

Synthesis of new TCH/Ni-based nanocomposite supported on SBA-15 and its catalytic application for preparation of benzimidazole and perimidine derivatives

A stable nickel-decorated SBA-15 nanocomposite (Ni/TCH@SBA-15) was synthesized through surface modification of silica nanoparticles with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform-infrared, field emission-scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA-15 (NNTS-15) was determined for the synthesis of 2-aryl-substituted benzimidazoles and 2,3-dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non-toxicity and clean reactions, mild reaction conditions and easy work-up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA-15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.

Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors

Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clinical emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound. Molecular dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.

Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst

In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.

Preparation, characterization, and application of 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride ionic liquid as an efficient catalyst for the synthesis of benzimidazole derivatives

In this study, 2,2′-bipyridine was treated with chlorosulfonic acid and 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride, [BiPy](SO3H)2Cl2, as a new ionic liquid catalyst was obtained and characterized with a variety of techniques including IR, 1H, and 13C NMR, Hammett acidity function as well as mass spectra method. After preparation and characterization, this ionic liquid was used as an efficient catalyst for the green and mild synthesis of benzimidazole derivatives. In addition, this reagent is efficiently able to catalyze the preparation of benzimidazole derivatives from the protected derivatives of aldehydes including oximes and semicarbazones. All reactions are performed under mild conditions in excellent yields.

One-pot synthesis of benzimidazoles in water in the presence of SiO 2-OPO3H

Silica-bound phosphoric acid (SiO2-OPO3H), as an eco-friendly, reusable, and heterogeneous catalyst, was applied for synthesis of 2-substituted benzimidazoles in water at 70°C. Very short reaction times, clean work-up, and high yields are among the advantages of this protocol.

DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media

An efficient synthetic method has been developed for the facile synthesis of 2-substituted benzimidazoles in organized aqueous media in the presence of a surfactant (viz. DBSA) as catalyst and I2 as co-catalyst. The method described has the advantages of operational simplicity, excellent yields, high chemoselectivity, and clean and green reaction profile.

New strategy for the synthesis of 2-phenylbenzimidazole derivatives with sodium perborate (SPB) as oxidant

A novel strategy for the synthesis of 2-phenylbenzimidazoles with sodium perborate (SPB) as oxidant under mild reaction condition is developed. Excellent chemoselectivity and broad substrate tolerance are the main advantages of this route.

Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity

Selectivity control during the formation of 1,2-disubstituted benzimidazoles has been achieved for the reaction of o-phenylenediamine with aldehydes in the presence of solid supported protic acids as catalysts and choosing an appropriate reaction medium. Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be the most effective catalyst system for the synthesis of 1,2-disubstituted benzimidazoles in EtOH at rt. Apart from the catalyst and solvent, the electronic and steric factors of the aldehyde and the electronic factor of the o-phenylenediamine are also significant contributory factors in dictating the selectivity. An understanding of the mechanistic course of the formation of the 1,2-disubstituted benzimidazoles has been outlined that would rationalise the origin of selectivity control under the set experimental parameters. The Royal Society of Chemistry.

Benzimidazole derivatives: Synthesis, leishmanicidal effectiveness, and molecular docking studies

Leishmanolysin GP63 is a zinc metalloprotease, expressed at the surface of Leishmania promastigotes. Studies on this protein are hindered as only a limited number of effective non-toxic inhibitors of this drug target are known. Present study describes the identification of a variety of 2-aryl- and 5-nitro-2-arylbenzimidazoles as new GP63 inhibitors. All the compounds were tested for in vitro activity against the promastigote form of Leishmania major and showed very good activity. 2-(Thiophen-2-yl)-1H-benzimidazole (19) and 2-(1H-indol-3-yl)-5-nitro-1H-benzimidazole (34) with IC50 value of 0.62 μg/mL were identified as lead of this library. Molecular docking studies were performed on binding site of GP63 to study the binding mode of compounds. The results of both in vitro and in silico studies clearly indicated that benzimidazoles may serve as new drug candidates in the combat against leishmaniasis.