384-46-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,1-methyl-2-(trifluoromethyl)-(9CI) is used as a building block in the synthesis of pharmaceutical compounds for its unique chemical properties. It aids in the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
1H-Benzimidazole,1-methyl-2-(trifluoromethyl)-(9CI) is used as a building block in the synthesis of agrochemicals for its unique chemical properties. It contributes to the development of new agrochemicals with enhanced performance and selectivity.
It is important to handle 1H-Benzimidazole,1-methyl-2-(trifluoromethyl)-(9CI) with caution, following proper safety protocols and guidelines.

Upstream product

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 76-05-1 trifluoroacetic acid 
• 49572-60-3 2-bromo-1-methyl-1H-benzo[d]imidazole 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 1632-83-3 1-Methylbenzimidazole 
• 2926-29-6 Langlois reagent 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 34734-15-1 1-methyl-2-iodo-1H-benzo[d]imidazole 
• 95-54-5 1,2-diamino-benzene 
• 612-28-2 2-nitro-N-methylaniline 
• 312-73-2 2-Trifluoromethylbenzimidazole 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Key intermediate for synthesizing 1-alkyl-2-trifluoromethyl-5-amino-1H-imidazole, and preparation method thereof

The invention discloses a key intermediate for synthesizing 1-alkyl-2-trifluoromethyl-5-amino-1H-imidazole, and a preparation method thereof. A purpose of the invention is mainly to solve the technical problem of lack of a 1-alkyl-2-trifluoromethyl-5-amino-1H-imidazole synthesis process in the prior art. The method comprises the following steps: carrying out alkylation on a compound II (2-trifluoromethylbenzimidazole) as a raw material to generate a compound III; opening a benzene ring through oxidizing to obtain a diacid compound IV; esterifying the compound IV to generate a compound V; carrying out monohydrolysis to obtain a compound VI; carrying out cutius rearrangement on the compound VI to generate a compound VII; hydrolyzing the ester group of the compound VII to generate a compoundVIII; and finally carrying out decarboxylation and tert-butyloxycarbonyl removal to obtain the compound I (1-alkyl-2-trifluoromethyl-5-amino-1H-imidazole).

A methodology for the photocatalyzed radical trifluoromethylation of indoles: A combined experimental and computational study

A methodology for the direct introduction of the trifluoromethyl group on to indole scaffolds is presented. The procedure involves the use of sodium trifluoromethylsulfinate (Langlois reagent) as the source of the trifluoromethyl radical, and is performed photochemically with 2-tert-butylanthraquinone as a photocatalyst. The reaction has also been probed computationally. Reaction kinetics and molecular orbital analyses from our quantum chemical computations successfully predict and rationalize the formation of the experimentally observed product and, in the case of 1-methylbenzimidazole, even reproduce the same qualitative trends in regioisomer preference.

FLUOROALKYLATING AGENT

Problem to be Solved It is intended to provide an industrially preferable fluoroalkylating agent and use thereof. Solution The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R1 is a C1 to C8 fluoroalkyl group; R2 and R3 are each independently a C1 to C12 alkyl group or the like; Y1 to Y4 are each independently a hydrogen atom, a halogen atom, or the like; and X? is a monovalent anion. A compound of the general formula (3): R4—S—R1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R4—S—Z wherein R4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).

Selective C-H trifluoromethylation of benzimidazoles through photoredox catalysis

The protocol presented here is a new strategy for visible light induced C-H trifluoromethylation at C4 of benzimidazoles using Togni's reagent in the presence of fac-Ir(ppy)3. Its advantages are its operational simplicity, mild reaction conditions, low catalyst loading and wide substrate scope in which electron-withdrawing, electron-donating groups and different protecting groups are tolerated.

A method for synthesizing three fluoromethylation aromatic hydrocarbon

The invention provides a synthetic method for a trifluoromethyl methylation arene. The trifluoromethyl methylation arene is prepared by reacting a halogenated arene, copper powder, elemental iodine and trifluoroacetic anhydride in an organic solvent under an inert atmosphere protection state. The method has the advantages of being simple and efficient, cheap in raw materials, low in synthetic cost, high in universality and repeatability, and the like, and can be popularized and applied to the fields of the synthesis of trifluoromethyl methylation aromatic derivatives.

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.

Copper-mediated perfluoroalkylation of heteroaryl bromides with (phen)CuRF

The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuR F, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF 2CF3 is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF2CF3 occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF3, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives.

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.

Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes

This article describes the copper-catalyzed oxidative trifluoromethylation of heteroarenes and highly electron-deficient arenes with CF 3SiMe3 through direct C-H activation. In the presence of catalyst Cu(OAc)2, ligand 1,10-phenanthroline and cobases tert-BuONa/NaOAc, oxidative trifluoromethylation of 1,3,4-oxadiazoles with CF3SiMe3 proceeded smoothly using either air or di-tert-butyl peroxide as an oxidant to give the corresponding trifluoromethylated 1,3,4-oxadiazoles in high yields. Di-tert-butyl peroxide was chosen as the suitable oxidant for oxidative trifluoromethylation of 1,3-azoles and perfluoroarenes. Cu(OH)2 and Ag2CO3 were the best catalyst and oxidant for direct oxidative trifluoromethyaltion of indoles. The optimum reaction conditions enable oxidative trifluoromethylation of a range of heteroarenes that bear numerous functional groups. The prepared trifluoromethylated heteroarenes are of importance in the areas of pharmaceuticals and agrochemicals. The preliminary mechanistic studies of these oxidative trifluoromethylations are also reported.

Copper-mediated trifluoromethylation of heteroaromatic compounds by trifluoromethyl sulfonium salts

Copper is king! A convenient method for the synthesis of trifluoromethylated heteroaromatic compounds under mild conditions has been developed based on the observation that 1 can be reduced by certain metals (see scheme). Substrate 1 is assumed to be reduced by copper via a single-electron transfer mechanism, and CuCF3 is the most probable intermediate in this reaction. DMF=N,N-dimethylformamide, Tf=triflate.