399-69-9

Usage

Uses

Used in Pharmaceutical Industry:
2,5-BIS(TRIFLUOROMETHYL)-1H-BENZIMIDAZOLE is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique chemical properties and stability, contributing to the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical sector, 2,5-BIS(TRIFLUOROMETHYL)-1H-BENZIMIDAZOLE is utilized as a building block for the creation of novel agrochemicals, enhancing crop protection and yield through the development of more effective and environmentally friendly products.
Used in Electronic Materials Industry:
2,5-BIS(TRIFLUOROMETHYL)-1H-BENZIMIDAZOLE is employed as a crucial component in the production of electronic materials, leveraging its thermal and chemical stability to improve the performance and reliability of electronic devices and components.
Used in Medicinal Chemistry Research:
2,5-BIS(TRIFLUOROMETHYL)-1H-BENZIMIDAZOLE is used as a subject of study in medicinal chemistry for its potential applications as an antimicrobial and antiviral agent, exploring its ability to combat various infectious diseases and contributing to the advancement of treatment options.

InChI:InChI=1/C9H4F6N2/c10-8(11,12)4-1-2-5-6(3-4)17-7(16-5)9(13,14)15/h1-3H,(H,16,17)

Upstream product

• 76-05-1 trifluoroacetic acid 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 185315-30-4 2,2,2-trifluoro-N-[4-(trifluoromethyl)phenyl]ethanimidoyl chloride 
• 1353778-33-2 2,2,2-trifluoro-N'-(3-(trifluoromethyl)phenyl)acetamidine 
• 1353778-34-3 2,2,2-trifluoro-N'-(4-(trifluoromethyl)phenyl)acetamidine 
• 69563-07-1 2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 

Relevant academic research and scientific papers

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.

An efficient method to access 2-fluoroalkylbenzimidazoles by PIDA oxidation of amidines

A mild and practical strategy for the synthesis of 2-bromodifluoromethyl (or trifluoromethyl)-1H-benzimidazoles via PIDA-mediated oxidative intramolecular cyclization of the fluorinated amidines is described. The approach has the advantages of superior yi

Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H- benzimidazole bioisosteres

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives with various 5- and 6-position bioisosteric substituents (-Cl, -F, -CF3, -CN), namely 1-7, were prepared using a short synthetic route. Each analogue was tested in vitro against the protozoa Giardia intestinalis and Trichomonas vaginalis in comparison with albendazole and metronidazole. Several analogues had IC50 values 1 μM against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)- bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T.:vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 μM, respectively). Studying further structure activity relationships through the use of bioisosteric substitution in these benzimidazolic derivatives should provide new leads against protozoal and possibly malarial diseases.

Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions

A high yielding one-pot procedure for the generation of 2-substituted benzimidazoles directly from 2-nitroanilines by in situ reduction and cyclization using a microwave procedure is described.

Synthesis of a series of trifluoromethylazoles and determination of pKa of acidic and basic trifluoromethyl heterocycles by 19F NMR spectroscopy

Trifluoroacetylation at the 5-position of 3,4-dihydro-2H-pyran and the 3-position of 4,5-dihydrofuran, followed by treatment with hydrazine, gave 3-(3-trifluoromethyl-1H-pyrazol-4-yl)propanol and 2-(3-trifluoromethyl-1H-pyrazol-4-yl)ethanol, respectively.In the latter case, an intermediate dimer was isolated.Isomeric 2-(3-trifluoromethyl-1H-pyrazol-5-yl)ethanol was formed by reaction of hydrazine with 6-benzyloxy-1,1,1-trifluorohex-3-yn-2-one and deprotection.Reaction of 3-benzyloxypropylamine with 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole, followed by deprotection, afforded 3-propanol.A series of 2-trifluoromethyl-1H-benzimidazoles and 2-trifluoromethyl-3H-imidazopyridines were prepared by condensation of the appropriate ortho-arenediamine with trifluoroacetic acid.Analysis of the 19F NMR spectra of the trifluoromethylazoles and of 3-trifluoromethylpyridine in aqueous solution at different pHs enabled determination of pKa values.All the compounds evaluated had one or more pKa between 1 and 13, except the triazole.Several compounds were identified as having potential use in measuring pH in biological media by 19F NMR spectroscopy.