327-19-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitro-2-trifluoromethylbenzimidazole is used as an antimicrobial agent for its demonstrated effectiveness against various fungi. Its unique structure allows for the development of new antifungal drugs, which can be crucial in treating fungal infections that are resistant to existing treatments.
Used in Materials Science:
5-Nitro-2-trifluoromethylbenzimidazole's trifluoromethyl group endows it with special electronic properties that can be harnessed in the development of new materials with tailored characteristics. This makes 5-Nitro-2-trifluoromethylbenzimidazole a candidate for use in advanced materials with specific electronic, optical, or chemical functionalities.
Used in Agrochemicals:
5-Nitro-2-trifluoromethylbenzimidazole is used as a starting material or intermediate in the synthesis of agrochemicals, particularly fungicides. Its antimicrobial properties can be leveraged to protect crops from fungal diseases, thereby increasing agricultural productivity and crop yields.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 5-Nitro-2-trifluoromethylbenzimidazole serves as a structural motif to modify the activity of biological molecules. Its incorporation into drug candidates can enhance their potency, selectivity, or pharmacokinetic properties, leading to the development of more effective therapeutic agents.

InChI:InChI=1/C8H3ClF6O2S/c9-18(16,17)6-3-4(7(10,11)12)1-2-5(6)8(13,14)15/h1-3H

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 76-05-1 trifluoroacetic acid 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 97-02-9 2,4-Dinitroanilin 
• 149623-84-7 N-(trifluoroacetyl)-2,4-dinitroaniline 
• 849435-68-3 N-(2-amino-4-nitro-phenyl)-2,2,2-trifluoro-acetamide 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 312-73-2 2-Trifluoromethylbenzimidazole 

Downstream Products

• 3671-66-7 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-amine 
• 83003-97-8 5-acetamido-2-(trifluoromethyl)benzimidazole 
• 233-55-6 imidazo<4,5-f>quinoline 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of a series of 2-trifluoromethylbenzimidazole-thiazolidinone derivatives

A series of 2-phenyl-3-(2-(trifluoromethyl)-1H-benzoimidazol-6-yl)thiazolidin-4-one derivatives were synthesized from p-nitro-o-phenylenediamine in a three-step reaction. Their structures were elucidated by NMR and mass spectral data. The synthesized comp

Cinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies

An approach in modern medicinal chemistry to discover novel bioactive compounds is by mimicking diverse complementary pharmacophores. In extension of this strategy, a new class of piperazine-linked cinnamide derivatives of benzimidazole-pyrimidine hybrids have been designed and synthesized. Their in vitro cytotoxicity profiles were explored on selected human cancer cell lines. Specifically, structural comparison of target hybrids with tubulin-DAMA-colchicine and tubulin-nocodazole complexes has exposed a deep position of benzimidazole ring into the αT5 loop. All the synthesized compounds were demonstrated modest to interesting cytotoxicity against different cancer cell lines. The utmost cytotoxicity has shown with an amine linker of benzimidazole-pyrimidine series, with specificity toward A549 (lung cancer) cell line. The most potent compound in this series was 18i, which inhibited cancer cell growth at micromolar concentrations ranging 2.21–7.29 μM. Flow cytometry studies disclosed that 18i inhibited the cells in G2/M phase of cell cycle. The potent antitumor activity of 18i resulted from enhanced microtubule disruption at a similar level as nocodazole on β-tubulin antibody, explored using immunofluorescence staining. The most active compound 18i also inhibited tubulin polymerization with an IC50 of 5.72 ± 0.51 μM. In vitro biological analysis of 18i presented apoptosis induction on A549 cells with triggering of ROS generation and loss of mitochondrial membrane potential, resulting in DNA injury. In addition, 18i displayed impairment in cellular migration and inhibited the colony formation. Notably, the safety profile of most potent compound 18i was revealed by screening against normal human pulmonary epithelial cells (L132: IC50: 69.25 ± 5.95 μM). The detailed binding interactions of 18i with tubulin was investigated by employing molecular docking, superimposition and free energy analyses. Thus remarks made in this study established that pyrimidine-benzimidazole hybrids as a new class of tubulin polymerization inhibitors with significant anticancer activity.

Fe(OTf)3-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o-arylenediamines and hexafluoroacetylacetone

An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure and readily available reagents.

Efficient syntheses of 2-fluoroalkylbenzimidazoles and -benzothiazoles

We report an efficient one-step route to 2-fluoroalkylbenzimidazoles and -benzothiazoles via the condensation of fluorinated carboxylic acids and aromatic diamines or aminothiophenols. Additionally, we describe the syntheses of fluoroalkyl-azabenzimidazoles, -purines, and -imidazolopyrazines. This method is high-yielding with broad scope and is operationally simple with potential application to parallel synthesis.

Design and synthesis of positional isomers of 1-alkyl-2-trifluoromethyl-5 or 6-substituted benzimidazoles and their antimicrobial activity

A series of novel positional isomers of 1-alkyl-2-trifluoromethyl benzimidazole derivatives 3a-j and 4a-j have been synthesized and screened for antibacterial activity against gram positive bacteria viz, Bacillus subtilis, Staphylococcus aureus and gram negative bacteria viz., Escherichia coli, Pseudomonas aeruginosa and antifungal activity against Candida albicans, Aspergillus niger, Rhizopus oryzae and Saccharomyces cerevisiae. Results indicate that compounds 3b, 4b were having promising antibacterial and antifungal activity.

One-pot synthesis of 2-trifluoromethyl and 2-difluoromethyl substituted benzo-1,3-diazoles

2-Trifluoromethyl and 2-difluoromethyl substituted benzimidazole, benzoxazole and benzothiazole derivatives were efficiently prepared through a one-pot reaction of trifluoroacetic acid and difluoroacetic acid, respectively, with commercially available o-p

Baker's yeast-mediated regioselective reduction of 2,4-dinitroacylanilines: Synthesis of 2-substituted 6-nitrobenzimidazoles

Several 2,4-dinitro-N-acylanilines were regioselectively reduced at the C-2 position by baker's yeast in slightly basic media (pH = 7.5) to afford 2-amino-4-nitroacylanilines, which were then cyclized under acidic conditions to the corresponding 2-substituted-6-nitrobenzimidazoles. The benzimidazoles thus obtained can be employed as precursors for bioactive derivatives.

Full length article

Cyclocondensation of N-(carbotrifluoromethyl)-ortho-arylenediamines leads to a series of 2-trifluoromethylarylimidazoles with good yields on montmorillonite K10 in 'dry media' under microwave irradiation within 2 min in a domestic oven. By conventional heating in the same conditions, no reaction is observed.

Potential radiosensitizing agents. 5. 2-Substituted benzimidazole derivatives

A series of 2-substituted benzimidazoles and their derivatives have been synthesized and tested for their ability to selectively sensitize hypoxic Chinese hamster cells (V-79) toward the lethal effect of ionizing radiation. These compounds were prepared by reacting the 2-substituted benzimidazoles with 1,2-epoxy-3-methoxypropane in the presence of potassium carbonate. Reaction of the 2-nitro and 2-methylsulfonyl analogue with the epoxide also yielded a cyclized material, which was confirmed to be a benzimidazo[2,1-b]oxazole. In an attempt to increase the electron affinity, 5- or 6-nitro-2-substituted-benzimidazoles were also synthesized and then reacted with the epoxide to yield the corresponding 1-substituted derivatives. The results of the biological tests for the radiosensitizing activity of these agents against Chinese hamster cells (V-79) in culture indicated the 2-nitro-substituted analogues were the most effective sensitizers in this series.