4423-09-0

Basic information

• Product Name: 3-(4-METHYLPHENYL)PYRIDINE
• Synonyms: 3-(4-METHYLPHENYL)PYRIDINE;AKOS BAR-0410;3-(p-Tolyl)pyridine;3-p-Tolylpyridine;3-(p-Methylphenyl)pyridine;4-(3-Pyridyl)toluene;5-(4-Methylphenyl)pyridine;4-(3-Pyridinyl)toluene
• CAS NO: 4423-09-0
• Molecular Formula: C₁₂H₁₁N
• Molecular Weight: 169.22
• Mol File: 4423-09-0.mol

Chemical Properties

• Melting Point: 38-39 °C
• Boiling Point: 293.9±9.0 °C(Predicted)
• Appearance: /
• Density: 1.030±0.06 g/cm3(Predicted)
• PKA: 5.08±0.10(Predicted)
• CAS DataBase Reference: 3-(4-METHYLPHENYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHYLPHENYL)PYRIDINE(4423-09-0)
• EPA Substance Registry System: 3-(4-METHYLPHENYL)PYRIDINE(4423-09-0)

Safety Data

• Hazardous Substances Data: 4423-09-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-METHYLPHENYL)PYRIDINE is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse medicinal compounds with potential applications in treating a wide range of diseases and conditions.
Used in Agrochemical Industry:
3-(4-METHYLPHENYL)PYRIDINE is utilized as a key component in the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these products helps enhance their effectiveness in controlling pests and weeds, thereby improving crop yields and ensuring food security.
Used in Coordination Chemistry:
3-(4-METHYLPHENYL)PYRIDINE is employed as a ligand in coordination chemistry, playing a crucial role in the formation of metal complexes. These complexes exhibit unique properties and applications in various fields, including catalysis, materials science, and supramolecular chemistry.
Used in Organic Synthesis:
3-(4-METHYLPHENYL)PYRIDINE is used as a reagent in organic synthesis, facilitating the formation of a variety of organic compounds. Its presence in reactions can enhance the yield and selectivity of desired products, making it a valuable tool in the synthesis of complex organic molecules.

Upstream product

• 110-86-1 pyridine 
• 51274-57-8 1-(4-Methylphenyl)-3,3-(1,5-pentanediyl)triazene 
• 599-66-6 bis(4-methylphenyl) sulfone 
• 106-38-7 para-bromotoluene 
• 89878-14-8 3-Diethylboranylpyridine 
• 626-55-1 3-Bromopyridine 
• 5720-05-8 4-methylphenylboronic acid 
• 626-60-8 3-Chloropyridine 
• 18412-57-2 p-tolyltriethoxysilane 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 
• 160688-99-3 [tris(3-pyridyl)boroxin] 
• 624-31-7 4-tolyl iodide 
• 1120-90-7 3-iodopyridine 
• 858364-75-7 N,N-diethyl pyridin-3-yl O-sulfamate 

Downstream Products

• 200282-69-5 3-(4-methylphenyl)pyridine N-oxide 
• 755699-91-3 3-(4-methylphenyl)piperidine 
• 200282-70-8 2-acetyl-3-(4-methylphenyl)pyridine 
• 143425-48-3 3-(4-methylphenyl)pyridine-2-carbonitrile 
• 179057-21-7 3-(4-Bromomethyl-phenyl)-pyridine 

Relevant articles and documents

Isotope Effects in the p-Tolylation of Pyridine

p-Toluoyl peroxide, p-iodotuluene, and di-p-tolyl sulfone, sulfoxide, and sulfide were photolyzed in an equimolar pyridine-pyridine-d5 mixture to give rise to isomeric p-tolylpyridines (α, β, and γ) and their deuterated compounds.Isotopic distribution ratios (YH/YD) in the isomeric products were determined to be slightly larger than unity.

Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls

Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

Suzuki-Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst

This paper describes the Suzuki Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PSPdONPs). The reaction of aryl bromides having electron-withdrawing groups or electron-donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of PdNPs was observed after the reaction.

New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions

A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.

para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator

Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Preparation method of para-substituted aryl compound

The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.

4-Amino-1,2,4-triazoles-3-thiones and 1,3,4-oxadiazoles-2-thiones·palladium(II) recoverable complexes as catalysts in the sustainable Suzuki-Miyaura cross-coupling reaction

The Suzuki-Miyaura cross-coupling reaction using 4-amino-1,2,4-triazoles and 1,3,4-oxadiazoles-2-thiones·palladium (II) is studied. The reaction is optimized and the most appropriate catalytic complex is tested with several aryl halides, boronic acids in an environmentally benign solvent system (H2O/EtOH). The recovery of the catalytic species is also surveyed because of the nature of the employed solvent. A domino process is efficiently carried out following the standard conditions. Several surface parameters of the ligands are analyzed and the resulting values are extrapolated to the insoluble palladium catalyst.

Salicylaldehyde-stabilized palladium nanoparticles for highly efficient suzuki-miyaura reaction at room temperature

Pd-catalyzed Suzuki-Miyaura cross-coupling reactions promoted by simple and commercial salicylaldehyde-based ligands were investigated. The effect of the ligands was evaluated and the reaction conditions were optimized. Moreover, the physical nature of the palladium was determined by TEM analysis and poison tests. It demonstrated that this catalytic system can be reused for ten consecutive runs and showed excellent activities toward aryl bromides with arylboronic acids at room temperature in air.

Bulk TiPd alloys as easily recyclable and preactivation-free heterogeneous catalysts for cross-coupling reactions

TiPd alloys have been found to be novel heterogeneous palladium catalysts for organic cross-coupling reactions. Catalyst preactivation is not necessary, resulting in facile recovery and reuse of the catalysts. Palladium is not leached into the reaction solution and the catalysts can be recycled several times without losing their catalytic activity.