1772-39-0

Basic information

• Product Name: 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole
• Synonyms: 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole;5-Nitro-2-(4-nitrophenyl)benziMidazole, 95%;5-Nitro-2-(4-nitrophenyl)-1H-benzoimidazole
• CAS NO: 1772-39-0
• Molecular Formula: C₁₃H₈N₄O₄
• Molecular Weight: 284.22702
• EINECS: 217-200-0
• Mol File: 1772-39-0.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 565.2°Cat760mmHg
• Flash Point: 295.6°C
• Appearance: /
• Density: 1.544g/cm³
• Vapor Pressure: 8.54E-13mmHg at 25°C
• Refractive Index: 1.74
• CAS DataBase Reference: 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole(1772-39-0)
• EPA Substance Registry System: 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole(1772-39-0)

Safety Data

• Hazardous Substances Data: 1772-39-0(Hazardous Substances Data)

Usage

General Description

5-nitro-2-(4-nitrophenyl)-1H-benzimidazole, also known as TATPB, is a chemical compound with two nitro groups and a benzimidazole ring. It is a yellow crystalline powder that is often used as a precursor for the synthesis of high-energy materials and as a stabilizer in explosives. TATPB has been studied for its potential use as an efficient and environmentally friendly oxidizing agent for organic synthesis and as a building block for the development of new pharmaceuticals. It has also been investigated for its potential as a corrosion inhibitor in metal surfaces. Due to its potentially harmful effects on human health and the environment, caution is advised when handling and using TATPB.

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

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

Downstream Products

• 7621-86-5 2-(4-aminophenyl)-5-amino-benzimidazole 
• 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 
• 71002-88-5 2-(4-aminophenyl)-5⁽⁶⁾-nitrobenzimidazole 

Relevant articles and documents

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.

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.

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.