4373-59-5

Usage

General Description

2-(4-Methylthiophenyl)pyridine is a chemical compound with the molecular formula C12H11NS. It consists of a pyridine ring with a 4-methylthiophenyl group attached to it. 2-(4-METHYLTHIOPHENYL)PYRIDINE is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It has been studied for its potential pharmacological properties, including its ability to act as an inhibitor of certain enzymes and as a potential anti-inflammatory agent. This chemical compound has a range of potential applications in the fields of medicinal chemistry and drug discovery.

Upstream product

• 391604-55-0 2-(2,4-difluorophenyl)pyridine 
• 1445591-09-2 2-(2,4-bis(methylthio)phenyl)pyridine 
• 109-04-6 2-bromo-pyridine 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 1778-09-2 4-(Methylthio)acetophenone 
• 109-76-2 Trimethylenediamine 
• 1765-93-1 4-fluoroboronic acid 
• 58861-53-3 4-fluorophenylpyridine 
• 5188-07-8 sodium thiomethoxide 
• 104-95-0 (4-bromophenyl)thioanisole 

Downstream Products

• 1345883-52-4 C₁₂H₁₀N₂O₂S 

Relevant academic research and scientific papers

A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles

A waste biomass, sodium lignosulfonate, was treated with sodium 2-formylbenzenesulfonate, and the phenylaldehyde condensation product was then used as a robust supporting material to immobilize a copper species. The so-obtained catalyst was characterized by many physicochemical methods including FTIR, EA, FSEM, FTEM, XPS, and TG. This catalyst exhibited excellent catalytic activity in the synthesis of nitrogen-containing heterocycles such as tricyclic indoles bearing 3,4-fused seven-membered rings, 2-arylpyridines, aminonaphthalenes and 3-phenylisoquinolines. In addition, this catalyst showed to be recyclable and could be reused several times without significant loss in activity during the course of the reaction process.

Ruthenium-Catalyzed meta-Selective C?H Mono- and Difluoromethylation of Arenes through ortho-Metalation Strategy

The first example for the ruthenium-catalyzed ligand-directed meta-selective C?H mono- and difluoromethylation is developed, affording a variety of new meta-mono- and difluoromethylated 2-phenylpyridines, 2-phenylpyrimidines, and 1-phenylpyrazoles in moderate-to-good yields. This new transformation exhibits broad substrate scope, good functional group tolerance, and high efficiency, and offers a practical approach to synthesize mono- and difluoromethylated arenes. Mechanistic studies indicate that a reaction pathway involving palladium-initiated radical species is involved in the catalytic cycle. The new dual catalytic system consisting of compatible ruthenium(II) and palladium(0) complexes enables the key processes of C?H activation and mono-/difluoromethyl-radical formation to occur and achieves the meta-selective functionalization efficiently. In addition, the present protocol can also be extended to non-fluoromethylation.

Colour tuning by the ring roundabout: [Ir(C^N)2(N^N)]+ emitters with sulfonyl-substituted cyclometallating ligands

A series of cationic bis-cyclometallated iridium(iii) complexes [Ir(C^N)2(N^N)]+ is reported. Cyclometallating C^N ligands are based on 2-phenylpyridine with electron-withdrawing sulfone substituents in the phenyl ring: 2-(4-methylsulfonylphenyl)pyridine (H1) and 2-(3-methylsulfonylphenyl)pyridine (H2). 2-(1H-Pyrazol-1-yl)pyridine (pzpy) and 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine (dmpzpy) are used as electron-rich ancillary N^N ligands. The complexes have been fully characterized and the single crystal structure of [Ir(2)2(dmpzpy)][PF6]·MeCN has been determined. Depending on the position of the methylsulfonyl group, the complexes are green or blue emitters with vibrationally structured emission maxima at 491, 523 nm for [Ir(1)2(N^N)][PF6] or 463, 493 nm for [Ir(2)2(N^N)][PF6] in MeCN solution. The marked vibrational structure and the absence of a rigidochromic shift, together with theoretical predictions based on density functional theory calculations, confirm the 3LC nature of the emitting triplet state. All four complexes have relatively high photoluminescence quantum yields in de-aerated solution (53 to 77%). On going from solution to powder samples, the emission is red-shifted and the quantum yields are considerably lower (≤11%). The complexes were tested in light-emitting electrochemical cells (LECs) achieving maximum luminances of 141 cd m-2 when operated at 100 A m-2 using pulsed current driving conditions.

Cobalt-catalyzed C-H cyanation of (Hetero)arenes and 6-Arylpurines with N -cyanosuccinimide as a new cyanating agent

A cobalt-catalyzed C-H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.

Green-emitting iridium(iii) complexes containing sulfanyl- or sulfone-functionalized cyclometallating 2-phenylpyridine ligands

A series of [Ir(C^N)2(bpy)][PF6] complexes in which the cyclometallating ligands contain fluoro, sulfane or sulfone groups is reported. The conjugate acids of the C^N ligands in the complexes are 2-(4-fluorophenyl)pyridine (H1), 2-(4-methylsulfonylphenyl)pyridine (H3), 2-(4-tbutylsulfanylphenyl)pyridine (H4), 2-(4- tbutylsulfonylphenyl)pyridine (H5), 2-(4- ndodecylsulfanylphenyl)pyridine (H6), 2-(4- ndodecylsulfonylphenyl)pyridine (H7). The single crystal structures of H3 and H5 are described. [Ir(C^N)2(bpy)][PF6] with C^N = 1, 3, 4, 5 and 7 were prepared from the appropriate [Ir2(C^N) 4Cl2] dimer and bpy; the structure of [Ir 2(3)4Cl2]·2CH2Cl2 was determined. [Ir(6)2(bpy)][PF6] was prepared by nucleophilic substitution starting from [Ir(1)2(bpy)][PF 6]. The [Ir(C^N)2(bpy)][PF6] complexes have been characterized by NMR, IR, absorption and emission spectroscopic and mass spectrometric methods. The single crystal structures of enantiomerically pure Δ-[Ir(1)2(bpy)][PF6] and of rac-4{[Ir(1) 2(bpy)][PF6]}·Et2O·2CH 2Cl2 are described, and the differences in inter-cation packing in the structures compared. [Ir(1)2(bpy)][PF6], [Ir(4)2(bpy)][PF6] and [Ir(6)2(bpy)][PF 6] (fluoro and sulfane substituents) are yellow emitters (λmaxem between 557 and 577 nm), and the room temperature solution emission spectra are broad. The sulfone derivatives [Ir(3)2(bpy)] [PF6], [Ir(5)2(bpy)][PF6] and [Ir(7) 2(bpy)][PF6] are green emitters and the emission spectra are structured (λmaxem = 493 and 523 to 525 nm). High photoluminescence quantum yields (PLQYs) of 64-74% are observed for the sulfone complexes in degassed solutions. The emission lifetimes for the three complexes containing sulfone substituents are an order of magnitude longer (2.33 to 3.36 μs) than the remaining complexes (0.224 to 0.528 μs). Emission spectra of powdered solid samples have also been recorded; the broad emission bands have values of λmaxem in the range 532 to 558 nm, and PLQYs for the powdered compounds are substantially lower (≤23%) than in solution. Trends in the redox potentials for the [Ir(C^N)2(bpy)][PF6] complexes are in accord with the observed emission behaviour. This journal is the Partner Organisations 2014.

Silyl-protected dioxaborinanes: Application in the Suzuki cross-coupling reaction

The synthesis of a range of novel silyl-protected dioxaborinanes as a column- and bench-stable boron reagent were found to be advantageous to achieving good yields in palladium-catalysed cross-coupling reactions under standard conditions. This journal is The Royal Society of Chemistry.

Traceless chelation-controlled rhodium-catalyzed intermolecular alkene and alkyne hydroacylation

A new functional-group tolerant, rhodium-catalyzed, sulfide-reduction process is combined with rhodium-catalyzed chelation-controlled hydroacylation reactions to give a traceless hydroacylation protocol. Aryl- and alkenyl aldehydes can be combined with both alkenes, alkynes and allenes to give traceless products in high yields. A preliminary mechanistic proposal is also presented. Traceless catalysis: The powerful combination of a chelation-controlled hydroacylation process and a new rhodium-catalyzed sulfide reduction gave the products of traceless hydroacylation. Aryl- and alkenyl aldehydes can be combined with alkenes, alkynes, and allenes to deliver traceless products in high yields (see scheme). Copyright

Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions

In search of alternatives to unstable or unreliable 2-pyridylboron reagents, we have explored two new varieties of solid, moderately air-stable 2-pyridylzinc reagents. Both reagents can be manipulated in air and are competent nucleophiles in Negishi cross-coupling reactions.

Synthesis, anti-inflammatory activity, and in vitro antitumor effect of a novel class of cyclooxygenase inhibitors: 4-(Aryloyl)phenyl methyl sulfones

Following our previous research on anti-inflammatory drugs (NSAIDs), we report on the design and synthesis of 4-(aryloyl)phenyl methyl sulfones. These substances were characterized for their capacity to inhibit cyclooxygenase (COX-1 and COX-2) isoenzymes. Molecular modeling studies showed that the methylsulfone group of these compounds was inserted deep in the pocket of the human COX-2 binding site, in an orientation that precludes hydrogen bonding with Arg120, Ser353, and Tyr355 through their oxygen atoms. The N-arylindole 33 was the most potent inhibitor of COX-2 and also the most selective (COX-1/COX-2 IC50 ratio was 262). The indole derivative 33 was further tested in vivo for its anti-inflammatory activity in rats. This compound showed greater inhibitory activity than ibuprofen. Other compounds (20, 26, 9, and 30) showed strong activity against carrageenan-induced inflammation. The latter compounds showed a weak capacity to inhibit the proliferation of human cell lines K562, NCI-H460, and HT-29 in vitro.