1792-40-1

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-NITRO-1H-BENZIMIDAZOLE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 2-METHYL-5-NITRO-1H-BENZIMIDAZOLE is utilized as an intermediate in the production of agrochemicals, potentially enhancing crop protection and yield through its incorporation into effective compounds.
Used in Organic Chemistry Research:
2-METHYL-5-NITRO-1H-BENZIMIDAZOLE is employed as a research compound in organic chemistry, where its unique structure allows for the exploration of new chemical reactions and the synthesis of novel organic molecules.
Used in Antimicrobial Applications:
2-METHYL-5-NITRO-1H-BENZIMIDAZOLE has been studied for its potential antimicrobial properties, making it a candidate for use in applications that require the inhibition of microbial growth, such as in medical or industrial settings.
Used in Anticancer Research:
2-METHYL-5-NITRO-1H-BENZIMIDAZOLE is also being investigated for its possible anticancer properties, with the aim of developing new therapeutic agents that could target and treat various types of cancer.

InChI:InChI=1/C8H7N3O2/c1-5-9-7-3-2-6(11(12)13)4-8(7)10-5/h2-4H,1H3,(H,9,10)

Upstream product

• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 25755-82-2 3-(4-methylphenyl)isoxazol-5(4H)-one 
• 25755-85-5 3-(4-chlorophenyl)isoxazol-5-(4H)-one 
• 31709-47-4 3-(4-methoxyphenyl)isoxazol-5(4H)-one 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 95-54-5 1,2-diamino-benzene 
• 57045-86-0 N-(2-bromo-4-nitro-phenyl)-acetamide 
• 124-42-5 acetamidine hydrochloride 
• 43154-39-8 N-acetyl-2-amino-5-nitroaniline 
• 57-55-6 propylene glycol 
• 64-17-5 ethanol 
• 75-36-5 acetyl chloride 

Downstream Products

• 14624-88-5 1-Benzyl-2-methyl-5-nitro-1H-benzimidazole 
• 27978-95-6 3-benzyl-2-methyl-5-nitro-3H-benzimidazole 
• 1428265-72-8 C₃₀H₃₃N₄O₈S^(1-)*Na⁽¹⁺⁾ 
• 1428265-73-9 C₃₂H₃₇N₄O₉S^(1-)*Na⁽¹⁺⁾ 
• 1428265-74-0 C₃₃H₃₉N₄O₉S^(1-)*Na⁽¹⁺⁾ 
• 1428265-75-1 C₃₂H₃₇N₄O₁₀S^(1-)*Na⁽¹⁺⁾ 
• 43154-50-3 2-methyl-5-nitro-1-(toluene-4-sulfonyl)-1H-benzoimidazole 
• 1609007-31-9 (E)-1-(2-methyl-6-nitro-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one 
• 503167-25-7 tert-butyl (3S,4S)-3-[(hydroxyamino)carbonyl]-4-({4-[(2-methyl-5-nitro-1H-benzimidazol-1-yl)methyl]benzoyl}amino)-1-pyrrolidinecarboxylate 
• 103393-69-7 3-ethyl-2-methyl-3H-benzimidazol-5-ylamine 
• 56842-62-7 5-acetamido-2-methylbenzimidazole 
• 82326-54-3 N-(2-methyl-1⁽³⁾H-benzoimidazol-5-yl)-benzamide 
• 14624-97-6 1-benzyl-2-methyl-1H-benzimidazol-5-ylamine 
• 111055-17-5 O-(2,4-Dichlorobenzyl)-1-benzyl-5-nitro-1H-benzimidazole-2-carboxaldehyde oxime 

Relevant academic research and scientific papers

Expeditious and efficient synthesis of benzoxazoles, benzothiazoles, benzimidazoles catalyzed by Ga(OTf)3 under solvent-free conditions

A new and efficient method for the synthesis of benzoxazoles, benzothiazoles, benzimidazoles from reactions of o-substituted aminoaromatics with orthoesters in the presence of catalytic amounts of Ga(OTf)3 under solvent-free conditions is presented. The remarkable features of this new protocol are high conversion, very short reaction times, cleaner reaction profiles under solvent-free conditions, straight forward procedure, and use of relatively non-toxic catalysts.

A highly effective sulfamic acid/methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature

Sulfamic acid/methanol was found to be an efficient catalytic system for the synthesis of benzimidazole compounds through the condensation of o-phenylenediamine with orthoester in high yields at room temperature.

Design, Synthesis, and Antimicrobial Evaluation of Novel Quinolone Imidazoles and Interactions with MRSA DNA

A novel series of quinolone imidazoles as new type of antimicrobial agents were synthesized. Most compounds exhibited good bioactivities especially against MRSA even superior to reference drugs. They induced bacterial resistance more slowly than clinical drugs and gave low cytotoxicity to human cells. The pKa values of these compounds showed appropriate ranges to pharmacokinetic behaviors. The interactions between compound 8b, Cu2+ ion, and MRSA DNA revealed that compound 8b could intercalate into DNA through copper ion bridge to form a steady 8b-Cu2+-DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. Study of compound 8b with human serum albumin indicated that compound 8b could be effectively stored and carried by human serum albumin.

Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines

(Chemical Equation Presented) Iodine was found to be an efficient catalyst for the synthesis of 2-substituted benzimidazoles by the condensation of orthoesters and 1,2-phenylenediamines in good to excellent yields under mild reaction conditions.

An efficient procedure for the synthesis of benzimidazole derivatives using Yb(OTf)3 as catalyst under solvent-free conditions

o-Diaminobenzene derivatives react smoothly with ortho-esters in the presence of 0.5 mol% of Yb(OTf)3 under solvent-free conditions to afford the corresponding benzimidazole derivatives in good to excellent yields. In addition, Yb(OTf)3 can be easily recovered almost quantitatively from the aqueous layer after the reaction was completed, and it could be reused with no loss of activity.

Novel silica tungstic acid (STA): Preparation, characterization and its first catalytic application in synthesis of new benzimidazoles

A novel silica tungstic acid (STA) as a highly efficient catalyst has been synthesized and employed for the cyclocondensation of 1,2-phenylenediamines with orthoesters under solvent-free conditions. Catalyst loadings can be as low as 1 mol% to give high yields of the corresponding benzimidazoles at 80 °C. To make the catalyst, sodium tungstate reacted with silica chloride under refluxing n-hexane. The STA as a novel solid acid was characterized by X-ray fluorescence, X-ray diffraction, and Fourier transform infrared spectroscopy.

Tungstate sulfuric acid: Preparation, characterization, and application in catalytic synthesis of novel benzimidazoles

Tungstate sulfuric acid (TSA) was prepared, characterized, and applied for direct synthesis of novel and known benzimidazoles through a condensation reaction of o-phenylenediamines with orthoesters under solvent-free conditions. TSA was characterized by powdered X-ray diffraction (XRD), X-ray fluorescence (XRF), and FTIR spectroscopy. This novel and eco-friendly method is very cheap and has many advantages such as excellent yields, recyclable and eco-friendly catalyst, and simple work-up procedure.

Homology modelling, molecular dynamics simulation and docking evaluation of β-tubulin of Schistosoma mansoni

Schistosomiasis is one of the neglected diseases causing considerable morbidity and mortality throughout the world. Microtubules with its main component, tubulin play a vital role in helminthes including schistosomes. Benzimidazoles represent potential drug candidates by binding β-tubulin. The study aimed to generate a homology model for the β-tubulin of S. mansoni using the crystal structure of O vis aries (Sheep) β-tubulin (PDB ID: 3N2G D) as a template, then different β-tubulin models were generated and two previously reported benzimidazole derivatives (NBTP-F and NBTP-OH) were docked to the generated models, the binding results indicated that both S. mansoni, S. haematobium were susceptible to the two NBTP derivatives. Additionally, three mutated versions of S. mansoni β-tubulin wild-type were generated and the mutation (F185Y) seems to slightly enhance the ligand binding. Dynamics simulation experiments showed S. haematobium β-tubulin is highly susceptible to the tested compounds; similar to S. mansoni, moreover, mutated models of S. mansoni β-tubulin altered its NBTPs susceptibility. Moreover, additional seven new benzimidazole derivatives were synthesized and tested by molecular docking on the generated model binding site of S. mansoni β-tubulin and were found to have good interaction inside the pocket.

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents

Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.