85237-71-4

Usage

Uses

Used in Chemical Synthesis:
5-Methyl-2-(p-tolyl)pyridine is used as an intermediate in chemical synthesis for the production of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the synthesis of target molecules.
Used as a Solvent:
Due to its solubility properties, 5-methyl-2-(p-tolyl)pyridine can be used as a solvent in certain chemical processes. Its ability to dissolve a variety of substances makes it a valuable component in the preparation of solutions for specific applications.
Used as a Building Block in Organic Chemistry:
5-Methyl-2-(p-tolyl)pyridine serves as a building block in organic chemistry, enabling the construction of more complex molecules. Its presence in a molecule can influence the reactivity and properties of the final product, making it a versatile component in the synthesis of various organic compounds.
Safety Considerations:
As an organically synthesized compound, 5-methyl-2-(p-tolyl)pyridine must be handled with care to prevent potential harmful effects. The specific safety and hazard details may vary depending on its concentration and usage, necessitating proper precautions during its application in different industries.

InChI:InChI=1/C13H13N/c1-10-3-6-12(7-4-10)13-8-5-11(2)9-14-13/h3-9H,1-2H3

Upstream product

• 3510-66-5 2-Bromo-5-methylpyridine 
• 5720-05-8 4-methylphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 195062-57-8 p-tolylboronic pinacol ester 
• 71-23-8 propan-1-ol 
• 68208-23-1 3-amino-3-p-tolylpropan-1-ol 

Downstream Products

• 676339-81-4 2-phenylpyridine-5,4’-dicarboxylic acid 

Relevant academic research and scientific papers

Organic electrode material and preparation method and application thereof

The invention relates to an organic electrode material and a preparation method and application thereof, and belongs to the technical field of materials. The organic electrode material belongs to conjugated carboxylate. The material is used as a working electrode of a sodium ion battery, the specific discharge capacities of an organic electrode material I-1 and an organic electrode material I-2 are 171mAh. g and 184mAh.g respectively after 100 cycles at the current density of 100mA/g, and half batteries prepared by taking I-1 and I-2 as the electrode materials can provide high specific capacity of 119mAh/g and 90mAh/g respectively in a voltage platform test process when 5C is 935mA/g. And the working voltages of the two materials both are between 0.4V and 0.7 V. The electrodematerial prepared by the method can be well applied to the sodium-ion battery, and has excellent oxidation-reduction capability and cycling stability when used as a negative electrode material. The organic electrode material is simple in preparation process and low in cost, and meets the requirement of large-scale preparation.

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.

Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons

The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R-B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.

Nitroarenes as the Nitrogen Source in Intermolecular Palladium-Catalyzed Aryl C–H Bond Aminocarbonylation Reactions

A three-component palladium-catalyzed aminocarbonylation of aryl and heteroaryl sp2 C?H bonds using nitroarenes as the nitrogen source was achieved using Mo(CO)6 as the reductant and origin of the CO. This intermolecular C?H bond functionalization does not requires any exogenous ligand to be added, and our mechanism experiments indicate that the palladacycle catalyst serves two roles in the aminocarbonylation reaction: reduce the nitroarene to a nitrosoarene and activate the sp2 C?H bond.

Straightforward installation of carbon-halogen, carbon-oxygen and carbon-carbon bonds within metal-organic frameworks (MOF) via palladium-catalysed direct C-H functionalization

The straightforward C-H functionalization of UiO-67-dcppy materials was realized by a Pd-catalysed PSM. This novel protocol provides an efficient method for the synthesis of various functionalized MOFs, which have shown promising adsorbent ability in removing phenolic contaminates from water. This journal is

Regioselectively functionalized pyridines from sustainable resources

Make the most of it! An Ir-catalyzed dehydrogenative condensation of alcohols and 1,3-amino alcohol was used to construct pyridine derivatives regioselectively. This method provides access to unsymmetrically substituted pyridines and tolerates a wide variety of functional groups. Three equivalents of H2 are generated per pyridine unit formed and the alcohol substrates become completely deoxygenated. Copyright

Palladium(ii) thiocarboxamide complexes: Synthesis, characterisation and application to catalytic Suzuki coupling reactions

A simple route to synthesise palladium(ii) complexes from the reaction of N-substituted pyridine-2-thiocarboxamide ligands and PdCl2(PPh 3)2 has been developed. The new complexes are very soluble in common solvents and have been fully characterised (elemental analysis, FT-IR, 1H, 31P, 13C-NMR), including an X-ray diffraction analysis. The molecular structures of all the complexes were determined and reveal the presence of square planar geometry around Pd with little distortion. The complexes were tested in the Suzuki coupling of electronically deactivated aryl and heteroaryl bromides and were found to have much greater activity, without using any promoting additives or phase transfer agent under aerobic conditions. Higher reaction rates are obtained by varying R substituents on the aromatic ring of pyridine-2-thiocarboxamide. The effect of other variables on the cross-coupling reaction, such as temperature, solvent and base, is also reported.

A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media

A fast protocol has been developed for the construction of 2-aryl-substituted pyridine derivatives by the oxygen-promoted, ligand-free, Pd(OAc)2-catalyzed Suzuki reaction of 2-halogenated pyridines in aqueous isopropanol.

Experimental and computational probes of a self-assembled capsule

This research was undertaken to explore the interior surface of a synthetic receptor 1.1 with arylpyridines as guests. The interior surface differentiates the guests through the recognition of their nitrogen atoms. Experimental and computational analyses revealed that there is a delicate balance of attractions and repulsions between the host and the lone pairs of guests.

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.