639782-24-4

Basic information

• Product Name: 2-Phenyl-3-(trifluoromethyl)-pyridine
• Synonyms: 2-Phenyl-3-(trifluoromethyl)-pyridine
• CAS NO: 639782-24-4
• Molecular Formula: C12H8F3N
• Molecular Weight: 223.2
• Mol File: 639782-24-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 286°C at 760 mmHg
• Flash Point: 126.8°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.00467mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 2-Phenyl-3-(trifluoromethyl)-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-3-(trifluoromethyl)-pyridine(639782-24-4)
• EPA Substance Registry System: 2-Phenyl-3-(trifluoromethyl)-pyridine(639782-24-4)

Safety Data

• Hazardous Substances Data: 639782-24-4(Hazardous Substances Data)

Usage

Description

2-Phenyl-3-(trifluoromethyl)-pyridine is a chemical compound with the molecular formula C12H8F3N, featuring a pyridine ring substituted with a phenyl group and a trifluoromethyl group. 2-Phenyl-3-(trifluoromethyl)-pyridine is recognized for its unique structure and properties, making it a valuable building block in organic synthesis and drug discovery research.

Uses

Used in Pharmaceutical Industry:
2-Phenyl-3-(trifluoromethyl)-pyridine is used as an intermediate in the synthesis of pharmaceuticals for its potential in creating anti-inflammatory and antibacterial drugs. Its unique structure allows for the development of medications that can address various health concerns.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Phenyl-3-(trifluoromethyl)-pyridine is utilized as a component in the development of crop protection products. Its incorporation aids in enhancing the effectiveness of these products, contributing to improved agricultural yields and protection against pests.
Used in Organic Synthesis:
2-Phenyl-3-(trifluoromethyl)-pyridine is employed as a valuable building block in organic synthesis, facilitating the creation of complex organic molecules. Its presence in these syntheses can lead to the development of novel compounds with diverse applications.
Used in Transition-Metal-Catalyzed Reactions:
2-Phenyl-3-(trifluoromethyl)-pyridine also serves as a potential ligand in transition-metal-catalyzed reactions. Its role in these reactions is crucial for the synthesis of intricate organic molecules, further expanding its utility in the field of chemistry.

InChI:InChI=1/C12H8F3N/c13-12(14,15)10-7-4-8-16-11(10)9-5-2-1-3-6-9/h1-8H

Upstream product

• 65753-47-1 2-chloro-3-trifluoromethyl-pyridine 
• 100-58-3 phenylmagnesium bromide 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 175205-82-0 2-bromo-3-(trifluoromethyl)-pyridine 
• 91182-50-2 3-bromo-2-phenyl pyridine 

Relevant articles and documents

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) cobalt hydride for Kumada coupling reactions

The electron-rich silylene Co(i) chloride 5 was obtained through the reaction of CoCl(PMe3)3 with chlorosilylene. Complex 5 reacted with 1,3-siladiazole HSiMe(NCH2PPh2)2C6H4 to give the silylene Co(iii) hydride 6 through chelate-assisted Si-H activation. To the best of our knowledge, complex 6 is the first example of Co(iii) hydride supported by N-heterocyclic silylene. Complexes 5 and 6 were fully characterized by spectroscopic methods and X-ray diffraction analysis. Complex 6 was used as an efficient precatalyst for Kumada cross-coupling reactions. Compared with the related complex 3 supported by only trimethylphosphine, complex 6 as a catalyst supported by both chlorosilylene and trimethylphosphine exhibits a more efficient performance for the Kumada cross-coupling reactions. A novel catalytic radical mechanism was suggested and experimentally verified. As an intermediate silylene cobalt(ii) chloride 6d was isolated and structurally characterized.

Decarboxylative Trifluoromethylating Reagent [Cu(O2CCF3)(phen)] and Difluorocarbene Precursor [Cu(phen)2][O2CCF2Cl]

This article describes the new economic decarboxylative trifluoromethylating reagent [Cu(phen)(O2CCF3)] (1; phen=1,10-phenanthroline) and the efficient difluorocarbene precursor [Cu(phen)2][O2CCF2Cl] (2). Treatment of copper tert-butoxide with phen and subsequent addition of trifluoroacetic acid or chlorodifluoroacetic acid afforded air-stable complexes 1 and 2, respectively, which were characterized by X-ray crystallography. The copper(I) ion in 1 is coordinated by a bidentate phen ligand, a monodentate trifluoroacetate group, and a molecule of CH3CN in a distorted tetrahedral coordination geometry. The molecular structure of 2 adopts an ionic form that consists of a [Cu(phen)2]+ cation and a chlorodifluoroacetate anion. Complex 1 reacted with a variety of aryl and heteroaryl halides to form trifluoromethyl (hetero)arenes in good yields. The corresponding Hammett plot exhibited a linear relationship and a reaction parameter (ρ)=+0.56±0.02, which indicated that the trifluoromethylation reaction proceeded via a nucleophilic reactive species. Complex 2 reacts with phenols to produce aryl difluoromethyl ethers in modest-to-excellent yields. Mechanistic investigations revealed that the difluoromethylation reaction proceeds by initial copper-mediated formation of difluorocarbene and subsequent concerted addition of difluorocarbene to the phenol to form a three-center transition state.