326-55-6

Usage

Uses

Used in Organic Synthesis:
5-Trifluoromethyl-1H-benzimidazole serves as a fundamental building block in organic synthesis, contributing to the creation of a wide array of chemical structures and compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 5-Trifluoromethyl-1H-benzimidazole is utilized for the preparation of various biologically active molecules. Its unique properties allow for the development of drugs with improved pharmacokinetic profiles.
Used in Drug Development:
The trifluoromethyl group present in 5-Trifluoromethyl-1H-benzimidazole is known to augment the metabolic stability and lipophilicity of the parent compounds, which is crucial for enhancing drug efficacy and safety.
Used in Therapeutic Applications:
5-Trifluoromethyl-1H-benzimidazole has been investigated for its potential therapeutic applications, particularly in the areas of antitumor and antiviral activities, indicating its broad spectrum of use in medicinal chemistry.
Used in Antitumor Research:
As a compound with antitumor potential, 5-Trifluoromethyl-1H-benzimidazole is explored for its capacity to combat cancer cells, offering a promising avenue for the development of novel cancer therapeutics.
Used in Antiviral Research:
Similarly, the compound has garnered interest for its possible antiviral properties, suggesting that it could be instrumental in the creation of treatments for viral infections.

InChI:InChI=1/C8H5F3N2/c9-8(10,11)5-1-2-6-7(3-5)13-4-12-6/h1-4H,(H,12,13)

Upstream product

• 51-17-2 benzoimidazole 
• 2314-97-8 iodotrifluoromethane 
• 86604-73-1 2-mercapto-5-trifluoromethyl-1H-benzimidazole 
• 2280-44-6 D-Glucose 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 
• 402-14-2 2-nitro-5-(trifluoromethyl)aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 124-38-9 carbon dioxide 
• 119072-55-8 tert-butylisonitrile 
• 2926-30-9 sodium triflate 
• 68-12-2 N,N-dimethyl-formamide 
• 64-18-6 formic acid 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 

Downstream Products

• 1181811-70-0 1-(2-methylallyl)-6-(trifluoromethyl)-1H-benzo[d]imidazole 
• 1181811-71-1 1-(2-methylallyl)-5-(trifluoromethyl)-1H-benzo[d]imidazole 
• 1135119-60-6 C₂₁H₁₄BrF₃N₂O₃S 
• 1135119-57-1 C₂₁H₁₄BrF₃N₂O₃S 
• 848393-37-3 2-(3-cyano-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-fluoro-4-(5-trifluoromethyl-benzoimidazol-1-yl)-phenyl]-amide 
• 774218-73-4 2-fluoro-4-(5-trifluoromethyl-benzoimidazol-1-yl)-phenylamine 

Relevant academic research and scientific papers

Visible-Light-Induced Trifluoromethylation of Highly Functionalized Arenes and Heteroarenes in Continuous Flow

We report a continuous-flow protocol for the trifluoromethylation of arenes, heteroarenes, and benzofused heterocycles. This photoredox methodology relies on the use of solid sodium trifluoromethanesulfinate (CF 3 SO 2 Na) as the trifluoromethylating agent and the iridium complex [Ir{dF(CF 3)ppy} 2 ](dtbpy)]PF 6 as the photoredox catalyst. A diverse set of highly functionalized heterocycles proved compatible with the methodology, and moderate to good yields were obtained within 30 minutes of residence time.

Selective Solvent-Assisted Linker Exchange (SALE) in a Series of Zeolitic Imidazolate Frameworks

Solvent-assisted linker exchange (SALE) has recently emerged as an attractive strategy for the synthesis of metal-organic frameworks (MOFs) that are unobtainable via traditional synthetic pathways. Herein we present the first example of selective SALE in which only the benzimiadazolate-containing linkers in a series of mixed-linker zeolitic imidazolate frameworks (ZIF-69, -78, and -76) are replaced. The resultant materials (SALEM-10, SALEM-10b, and SALEM-11, respectively) are isostructural to the parent framework and in each case contain trifluoromethyl moieties. We therefore evaluated each of these materials for their hydrophobicity in condensed and gas phases. We expect that selective SALE will significantly facilitate the design of improved, and potentially complex, MOF materials with new and unusual properties.

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.

Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.

SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d -Glucose with o-Phenylenediamines in Water

d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, water as an environmentally benign solvent, and the synthesis of vitamin B12 component on the gram scale.

A benzimidazole and synthetic method of derivative thereof (by machine translation)

The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)