51310-55-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Trifluoromethyl-1H-indole is used as a key building block for the synthesis of various pharmaceutical compounds. Its unique structure contributes to the development of new drugs with improved biological activity and stability, which is crucial for enhancing the efficacy and safety of medications.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Trifluoromethyl-1H-indole serves as a fundamental component in the creation of novel pesticides. Its incorporation into these compounds can lead to more effective and environmentally friendly pest control solutions.
Used in Organic Synthesis:
3-Trifluoromethyl-1H-indole is utilized as a reagent in organic synthesis to introduce the trifluoromethyl group into other molecules. This modification can significantly improve the biological activity and stability of the synthesized compounds, broadening their range of applications in various fields.
Used in Material Science:
3-Trifluoromethyl-1H-indole is explored for its potential applications in material science, where its unique properties may contribute to the development of advanced materials with specific characteristics required for various industrial applications.
Used in Catalysis:
3-TRIFLUOROMETHYL-1H-INDOLE is also studied for its role in catalysis, where it may enhance the efficiency of chemical reactions, leading to more sustainable and cost-effective processes in the chemical industry.

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

Upstream product

• 120-72-9 indole 
• 1184-76-5 difluorodiiodomethane 
• 383-73-3 bis(trifluoroacetyl)peroxide 
• 2314-97-8 iodotrifluoromethane 
• 887144-94-7 Togni's reagent II 
• 26340-47-6 3-Iodo-1H-indole 
• 2926-29-6 Langlois reagent 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 17983-42-5 trimethylsilyl indole 

Relevant academic research and scientific papers

Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived ligandless CuCF3

We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)-I bond using fluoroform-derived ligandless CuCF3. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting products enabled the controlled, late-stage synthesis of single regioisomers of complex CF3-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.

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.

For the production of sulfur [...] hydrocarbon or heteroaromatic hydrocarbon compound and its preparation method (by machine translation)

The invention discloses a trifluoro-methylthio arene or azacalixarene compound and a preparation method thereof. The preparation method of the trifluoro-methylthio arene or azacalixarene compound comprises the following steps: in an organic solvent, carrying out substitution reaction on a compound shown in a formula I and nitrogen-trifluoro-methylthio saccharin shown in a formula II in presence of a catalyst, so that a compound shown in a formula III is obtained. The preparation method of the trifluoro-methylthio arene or azacalixarene compound has the advantages that reaction materials can be easily controlled to be in single substitution, toxicity is low, and environmental protection is realized; meanwhile, application range of substrate is wide, equipment requirement is low, and operation is simple. The general formula (I), the general formula (II) and the formula (III) are described in the specification.

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.

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.

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.

New Reagent for Highly Efficient Synthesis of Trifluoromethyl-Substituted Arenes and Heteroarenes

A new reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported for the introduction of a -CF3 group to arenes and heteroarenes. Compared with current known reagents, TCDA shows very broad scope with respect to electron-deficient, -neutral, and -rich aryl/heteroaryl iodides as well as excellent functional group tolerance, including ester, amide, aldehyde, hydroxyl, and carboxylic acid. (Chemical Equation Presented).

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.

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.