119811-95-9

Basic information

• Product Name: 2-(4-methylphenyl)-5-(trifluoromethyl)pyridine
• Synonyms: 2-p-Tolyl-5-trifluoromethyl-pyridine
• CAS NO: 119811-95-9
• Molecular Formula: C₁₃H₁₀F₃N
• Molecular Weight: 237.2204
• Mol File: 119811-95-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 282.167°C at 760 mmHg
• Flash Point: 124.451°C
• Density: 1.2g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 2-(4-methylphenyl)-5-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylphenyl)-5-(trifluoromethyl)pyridine(119811-95-9)
• EPA Substance Registry System: 2-(4-methylphenyl)-5-(trifluoromethyl)pyridine(119811-95-9)

Safety Data

• Hazardous Substances Data: 119811-95-9(Hazardous Substances Data)

Usage

General Description

2-(4-methylphenyl)-5-(trifluoromethyl)pyridine is a chemical compound with the molecular formula C14H10F3N. It is a pyridine derivative that contains a trifluoromethyl group and a 4-methylphenyl group. It is used in the synthesis of pharmaceuticals and agrochemicals, and as a building block for the preparation of various organic compounds. This chemical has potential applications in the fields of medicine, agriculture, and materials science due to its unique chemical properties. Additionally, it is important for researchers and chemists to understand the reactivity, physical properties, and potential hazards associated with this compound when handling and using it in laboratory settings.

Upstream product

• 62230-47-1 p-methylbenzamidrazone 
• 52334-81-3 2-chloro-5-trifluoromethylpyridine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-38-7 para-bromotoluene 
• 195062-57-8 p-tolylboronic pinacol ester 
• 50488-42-1 2-bromo-5-(trifluoromethyl)pyridine 
• 76041-72-0 2-mercapto-5-trifluoromethylpyridine 
• 106-43-4 para-chlorotoluene 
• 5720-05-8 4-methylphenylboronic acid 
• 867380-38-9 5-bromo-2-(4-methylphenyl)pyridine 
• 13534-97-9 6-bromopyridine-3-amine 
• 170850-45-0 3-amino-6-(4-methylphenyl)pyridine 
• 119811-56-2 5-chloro-3-(p-tolyl)-6-trifluoromethyl-1,2,4-triazine 
• 119811-40-4 3-(p-tolyl)-6-trifluoromethyl-1,2,4-triazin-5(2H)-one 

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.

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Heterocyclic Allylsulfones as Latent Heteroaryl Nucleophiles in Palladium-Catalyzed Cross-Coupling Reactions

Heterocyclic sulfinates are effective reagents in palladium-catalyzed coupling reactions with aryl and heteroaryl halides, often providing high yields of the targeted biaryl. However, the preparation and purification of complex heterocylic sulfinates can be problematic. In addition, sulfinate functionality is not tolerant of the majority of synthetic transformations, making these reagents unsuitable for multistep elaboration. Herein, we show that heterocyclic allylsulfones can function as latent sulfinate reagents and, when treated with a Pd(0) catalyst and an aryl halide, undergo deallylation, followed by efficient desulfinylative cross-coupling. A broad range of allyl heteroarylsulfones are conveniently prepared, using several complementary routes, and are shown to be effective coupling partners with a variety of aryl and heteroaryl halides. We demonstrate that the allylsulfone functional group can tolerate a range of standard synthetic transformations, including orthogonal C- and N-coupling reactions, allowing multistep elaboration. The allylsulfones are successfully coupled with a variety of medicinally relevant substrates, demonstrating their applicability in demanding cross-coupling transformations. In addition, pharmaceutical agents crizotinib and etoricoxib were prepared using allyl heteroaryl sulfone coupling partners, further demonstrating the utility of these new reagents.