51310-54-4

Usage

Uses

Used in Pharmaceutical Research and Development:
2-Trifluoromethylindole is utilized as a key intermediate in the synthesis of new drugs, leveraging its unique chemical properties to enhance the development of biologically active pharmaceuticals.
Used in Agrochemical Development:
2-Trifluoromethylindole also serves as a crucial component in the creation of new agrochemicals, contributing to advancements in agricultural chemistry for more effective crop protection and management.
Used in the Synthesis of Fluorinated Pharmaceuticals:
2-Trifluoromethylindole is particularly valuable in the synthesis of fluorinated pharmaceuticals due to its trifluoromethyl groups. These fluorinated drugs often exhibit improved bioavailability and metabolic stability compared to non-fluorinated versions, offering significant benefits in therapeutic applications across various industries.

InChI:InChI=1/C9H6F3N/c10-9(11,12)8-5-6-3-1-2-4-7(6)13-8/h1-5,13H

Upstream product

• 120-72-9 indole 
• 2314-97-8 iodotrifluoromethane 
• 3396-11-0 cesium acetate 
• 95-53-4 o-toluidine 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 2926-29-6 Langlois reagent 
• 77152-08-0 trifluoromethylcopper(I) 
• 497236-62-1 N-(2-ethynylphenyl)-4-toluenesulfonamide 
• 887144-94-7 Togni's reagent II 
• 17983-42-5 trimethylsilyl indole 
• 383-73-3 bis(trifluoroacetyl)peroxide 
• 1184-76-5 difluorodiiodomethane 

Downstream Products

• 132502-93-3 2-trifluoromethyl-indole-3-acetic acid 
• 1415716-58-3 (E)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide 
• 1609030-70-7 (E)-3-(4-methoxyphenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide 
• 1416881-63-4 (E)-3-(4-fluoro-3,5-dimethylphenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide 
• 1609030-87-6 (E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide 
• 1609030-96-7 (E)-3-(4-(2-hydroxyethoxy)-3,5-dimethoxyphenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide 
• 1542707-17-4 N-benzyl-2-[2-(trifluoromethyl)-1H-indol-1-yl]-5,6,7,8-tetrahydroquinazolin-4-amine 

Relevant academic research and scientific papers

Photoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes

We describe a series of air-stable NiIII complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF3 ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These NiIII complexes act as efficient catalysts for photoinduced C(sp2)?H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.

Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes

This Article describes the development of a stable NiIV complex that mediates C(sp2)-H trifluoromethylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C-H trifluoromethylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving NiIV, NiIII, and NiII intermediates.

Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines

A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy

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.

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp3)-H Functionalization of Trifluoroacetimidoyl Chlorides

Perfluoroalkylated indoles are valuable compounds in drug discovery. A Pd(0)-catalyzed C(sp3)-H functionalization enables access to 2-(trifluoromethyl)indoles from trifluoroacetimidoyl chlorides. These are stable compounds, easily obtained from

Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex

A well-defined copper complex bearing iminosemiquinone ligands performs single electron reduction of an electrophilic CF3+ source into CF3 radicals. This redox behavior is enabled by the ligand which shuttles through two different redox states (iminosemiquinone and iminobenzoquinone) while the copper center is preserved as a Cu(ii). This system was used in the trifluoromethylation of silyl enol ethers, heteroaromatics and in the hydrotrifluoromethylation of alkynes. This is the first example of cooperative redox catalysis for the controlled generation of CF3 radicals.

Iron-catalyzed trifluoromethylation of enamide

Herein the first example of the iron(II)-catalyzed trifluoromethylation of enamide using mild and simple reaction conditions is reported. The method is cost-effective and uses the easy-to-handle Togni's reagent as the electrophilic CF3 source. This transformation is totally regioselective at the C3 position of enamides and exhibits broad substrate scope, good functional group tolerance and thus demonstrates its useful application in a late-stage fluorination strategy.

Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide

Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously.

Photoinduced Electron-transfer Reaction of Difluorodiiodomethane with Azaaromatic Compounds and Enamines

Irradiation of difluorodiiodomethane 1 with pyrroles, indole and imidazoles in dimethylformamide gives the corresponding trifluoromethylated products, whereas irradiation with enamines results in 2-trifluoromethyl ketones.A photoinduced electron-transfer mechanism is proposed.

Perfluoroalkylations of Nitrogen-containing Heteroaromatic Compounds with Bis(perfluoroalkanoyl) Peroxides

Perfluoroalkylations of nitrogen-containing heteroaromatic compounds with bis(perfluoroalkanoyl) peroxides were studied.Bis(trifluoroacetyl) peroxide, bis(heptafluorobutyryl) peroxide, and bis(pentadecafluoro-octanoyl) peroxide were found to be useful and effective reagents for perfluoromethylations, perfluoropropylations or perfluoroheptylations of pyrrole and its derivatives, while these peroxide could not be applied for the perfluoroalkylations of pyridine or imidazole.For the perfluoroalkylations with the peroxides, electron transfer from the substrate to the peroxide, which affords a perfluoroalkyl radical of the substrate in a solvent cage, is proposed.In pyrrols, since the delocalization of the N lone pair to ?-systems lowers the nucleophilicity of the N lone pair and increases the electron density at the ?-orbital, the electron transfer readily occurred and perfluoroallkylated pyrroles were obtained in good yield and regioselectively.However, nucleophilic attack of the lone pair to the O-O bond of the peroxide was superior to the electron transfer in pyridine or imidazole of which the N lone pairs are very nucleophilic.