851775-42-3

Usage

General Description

2-(3-methylphenyl)-5-methylpyridine is a chemical compound with a molecular formula C13H13N. It is a derivative of pyridine, containing both a methyl group and a 3-methylphenyl group attached to the pyridine ring. 2-(3-methylphenyl)-5-methylpyridine is used in organic synthesis and pharmaceutical research as a building block for the preparation of various biologically active molecules. It has potential applications as an intermediate for the synthesis of pharmaceuticals, agrochemicals, and other functional organic materials. Its structure and properties make it useful for the development of new drugs with therapeutic potential. However, it also has potential hazards and should be handled and used with care in a controlled environment.

Upstream product

• 78-85-3 2-methylpropenal 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 253342-48-2 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane 
• 591-17-3 meta-bromotoluene 
• 17933-03-8 m-tolylboronic acid 

Downstream Products

• 1401518-49-7 2-(4'-methoxy-4-methyl-[1,1'-biphenyl]-2-yl)-5-methylpyridine 
• 1447828-37-6 2-[(2-benzoyl-5-methyl)phenyl]-5-methylpyridine 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Facile synthesis of cyclometalated ruthenium complexes with substituted phenylpyridines

We have developed a new strategy that uses the Kroehnke synthesis for the preparation of various substituted phenylpyridines in excellent yields (up to 88%). Starting with the appropriate commercially available acetophenone, a variety of phenylpyridines substituted by either electron-donating (i.e. methyl, methoxy) or -withdrawing groups (i.e. bromide, nitro) on the phenyl ring are obtained in a two-step synthesis. The corresponding functionalized cyclometalated ruthenium complexes can be prepared with unusually high yields by using methanol as reaction solvent. The electrochemical data of the complexes demonstrate the strong σ-donating character of the anionic phenylpyridine ligand. X-ray analyses of four complexes show a shortening of the Ru-C bond associated with the elongation of only one of the five Ru-N bonds (trans effect). Wiley-VCH Verlag GmbH & Co, KGaA, 2006.

Effect of substitution of methyl groups on the luminescence performance of IrIII complexes: Preparation, structures, electrochemistry, photophysical properties and their applications in organic light-emitting diodes (OLEDs)

A series of dimethyl-substituted tris(pyridylphenyl)iridium(III) derivatives [(n-MePy-n′-MePh)3Ir] [n = 3, n′ = 4 (1); n = 4, n′ = 4 (2); n = 4, n′ = 5 (3); n = 5, n′ = 4 (4); n = 5, n′ = 5 (5)] have been synthesized and characterized to investigate the effect of the substitution of methyl groups on the solid-state structure and photo- and electroluminescence. The absorption, emission, cyclic voltammetry and electroluminescent performance of 1-5 have also been systematically evaluated. The structures of 2 and 4 have been determined by a single-crystal X-ray diffraction analysis. Under reflux (> 200 °C) in glycerol solution, fac-type complexes with a distorted octahedral geometry are predominantly formed as the major components in all cases. Electrochemical studies showed much smaller oxidation potentials relative to Ir(ppy)3 (Hppy = 2-phenylpyridine). All complexes exhibit intense green photoluminescence (PL), which has been attributed to metal-to-ligand charge transfer (MLCT) triplet emission. The maximum emission wavelengths of thin films of 1, 3, 4 and 5 at room temperature are in the range 529-536 nm, while 2 displays a blue-shifted emission band (λmax = 512 nm) with a higher PL quantum efficiency (ΦPL = 0.52) than those of complexes 1 and 3-5; this is attributed to a decrease of the intermolecular interactions. Multilayered organic light-emitting diodes (OLEDs) were fabricated by using three (2, 3 and 4) of these IrIII derivatives as dopant materials. The electroluminescence (EL) spectra of the devices, which have the maximum peaks at 509-522 nm, with shoulder peaks near 552 nm, are consistent with the PL spectra in solution at 298 K. The devices show operating voltages at 1 mA/cm 2 of 4,9, 5.6, 5,1, and 4.6 V for Ir(ppy)3, 2, 3, and 4, respectively. In particular, the device with 2 shows a higher external quantum efficiency (ηext = 11% at 1 mA/cm2) and brightness (4543 cd/m2 at 20 mA/cm2) than Ir(ppy)3 (ηext = 6.0% at 1 mA/cm2; 3156 cd/m2 at 20 mA/cm2) and other Ir(dmppy)3 derivatives, (dmppy = dimethyl-substituted ppy), under the same conditions. The methyl groups at the meta (Ph) and para (Py) positions to the Ir metal atom have a great influence on absorption, emission, redox potentials and electroluminescence. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.