913955-35-8

Basic information

• Product Name: 3-Methyl-2-(trifluoromethyl)-1H-indole
• Synonyms: 3-METHYL-2-TRIFLUOROMETHYLINDOLE;3-Methyl-2-(trifluoromethyl)-1H-indole
• CAS NO: 913955-35-8
• Molecular Formula: C₁₀H₈F₃N
• Molecular Weight: 199.17
• Mol File: 913955-35-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 266 °C
• Flash Point: 115 °C
• Appearance: /
• Density: 1.313
• Vapor Pressure: 0.0141mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: 2-8°C
• PKA: 14.92±0.30(Predicted)
• CAS DataBase Reference: 3-Methyl-2-(trifluoromethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-(trifluoromethyl)-1H-indole(913955-35-8)
• EPA Substance Registry System: 3-Methyl-2-(trifluoromethyl)-1H-indole(913955-35-8)

Safety Data

• Hazardous Substances Data: 913955-35-8(Hazardous Substances Data)

Usage

Description

3-Methyl-2-(trifluoromethyl)-1H-indole is an organic compound that belongs to the indole family. It is characterized by the presence of a methyl group at the 3-position and a trifluoromethyl group at the 2-position on the indole ring. 3-Methyl-2-(trifluoromethyl)-1H-indole is synthesized through the trifluoromethylation of arenes and heteroarenes using a rhenium catalyst and hypervalent iodine reagents.

Uses

Used in Pharmaceutical Industry:
3-Methyl-2-(trifluoromethyl)-1H-indole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
3-Methyl-2-(trifluoromethyl)-1H-indole is also utilized in chemical research as a model compound to study the reactivity and properties of indole derivatives. This helps researchers to better understand the behavior of similar compounds and develop new synthetic methods or applications.
Used in Material Science:
3-Methyl-2-(trifluoromethyl)-1H-indole may also find applications in material science, particularly in the development of new materials with specific properties. For example, its incorporation into polymers or other materials could lead to the creation of novel materials with improved characteristics, such as enhanced stability or specific binding affinities.

InChI:InChI=1/C10H8F3N/c1-6-7-4-2-3-5-8(7)14-9(6)10(11,12)13/h2-5,14H,1H3

Upstream product

• 83-34-1 3-Methylindole 
• 2314-97-8 iodotrifluoromethane 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 887144-94-7 Togni's reagent II 
• 100074-04-2 1-fluoro-4-(pent-4-en-1-yl)benzene 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 2926-30-9 sodium triflate 
• 2926-29-6 Langlois reagent 
• 129946-88-9 Umemoto's reagent 
• 887144-97-0 Togni's reagent 

Downstream Products

• 132502-93-3 2-trifluoromethyl-indole-3-acetic acid 
• 934843-29-5 dimethyl-2-{[1-(4-chlorobenzoyl)-2-(trifluoromethyl)indol-3-yl]methyl}malonate 
• 929075-62-7 [3-(bromomethyl)-2-(trifluoromethyl)-1H-indol-1-yl](4-chlorophenyl)methanone 
• 913955-36-9 (4-chloro-phenyl)[3-methyl-2-(trifluoromethyl)-1H-indol-1-yl]-methanone 

Relevant articles and documents

Nickel-Catalyzed C–H Trifluoromethylation of Electron-Rich Heteroarenes

The first example of a nickel-catalyzed C–H trifluoromethylation of electron-rich heteroarenes, including imidazopyridines, indoles and thiophenes, has been developed with the commercially available and relatively inexpensive industrial raw material iodotrifluoromethane (CF3I) as the trifluoromethylating reagent. The synthetic potential of this method is demonstrated by its successful application to the direct trifluoromethylation of the biologically active molecules melatonin and zolmitriptan. (Figure presented.).

Control of site selectivity in trifluoromethylation of alkenes bearing a pendant indolyl group: Synthesis of CF3-containing tetrahydrocarbazoles

We present a tetrahydrocarbozole-forming carbo-trifluoromethylation of indoles bearing an alkenyl group at the C3 position. The reaction proceeded selectively with the combination of TsOH·H2O as a catalyst and CH2Cl2 as a solvent. The site-selectivity could be altered by changing the reaction solvent; the use of THF instead of CH2Cl2 increased the formation of aromatic trifluoromethylation products.

Exploring the Structure and Performance of Cd–Chalcogenide Photocatalysts in Selective Trifluoromethylation

The field of heterogeneous photoredox catalysis has grown substantially and impacted organic synthesis because of the affordability and reusability of catalysts. This study reports radical trifluoromethylation with Cd–chalcogenide semiconductors. Cd semiconductors, particularly CdSe, are readily available, commercial, visible-light-responsive, heterogeneous photocatalysts. The potential of readily available Cd semiconductors, particularly CdSe, is confirmed by their increased photocatalytic activity toward trifluoromethylation with various substrates, such as (hetero)arenes and vinylic amides/acids, via addition, cyclization, and decarboxylation under visible light. The economic significance of this strategy is also highlighted through the scalable synthesis of biologically active molecules followed by catalyst reuse. Moreover, these catalysts are relatively inexpensive compared with transition metal-based homogeneous photocatalysts, presently used in organic synthesis.

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.