51310-54-4

Basic information

• Product Name: 2-Trifluoromethylindole
• Synonyms: 2-TRIFLUOROMETHYL-1H-INDOLE;2-TRIFLUOROMETHYLINDOLE;1 H-INDOLE, 2-(TRIFLUOROMETHYL)
• CAS NO: 51310-54-4
• Molecular Formula: C₉H₆F₃N
• Molecular Weight: 185.15
• Product Categories: API intermediates
• Mol File: 51310-54-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 106-110°C
• Boiling Point: 256.676 °C at 760 mmHg
• Flash Point: 109.034 °C
• Appearance: /
• Density: 1.368 g/cm³
• Vapor Pressure: 0.024mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.62±0.30(Predicted)
• CAS DataBase Reference: 2-Trifluoromethylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Trifluoromethylindole(51310-54-4)
• EPA Substance Registry System: 2-Trifluoromethylindole(51310-54-4)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 51310-54-4(Hazardous Substances Data)

Usage

General Description

2-Trifluoromethylindole is a chemical compound with the molecular formula C9H6F3N. It is a derivative of indole, a heterocyclic organic compound, with the addition of three trifluoromethyl groups. 2-Trifluoromethylindole is used in various research and pharmaceutical applications, particularly in the development of new drugs and agrochemicals. 2-Trifluoromethylindole has potential as a building block for the synthesis of biologically active molecules due to its unique and versatile chemical properties. Its trifluoromethyl groups also make it particularly valuable for the development of fluorinated pharmaceuticals, which have shown enhanced bioavailability and metabolic stability compared to their non-fluorinated counterparts.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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