29335-87-3

Basic information

• Product Name: Pyridine, 2-[(4-methylphenyl)methyl]-
• CAS NO: 29335-87-3
• Molecular Formula: C13H13N
• Molecular Weight: 183.253
• Mol File: 29335-87-3.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: Pyridine, 2-[(4-methylphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-[(4-methylphenyl)methyl]-(29335-87-3)
• EPA Substance Registry System: Pyridine, 2-[(4-methylphenyl)methyl]-(29335-87-3)

Safety Data

• Hazardous Substances Data: 29335-87-3(Hazardous Substances Data)

Upstream product

• 20531-88-8 2-(4-methylbenzyl) pyridine 1-oxide 
• 372-48-5 2-fluoropyridine 
• 104-82-5 4-Methylbenzyl chloride 
• 109-09-1 2-chloropyridine 
• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 122058-30-4 p-methylcinnamyl alcohol 
• 694-59-7 pyridine N-oxide 
• 109-04-6 2-bromo-pyridine 
• 104-81-4 4-Methylbenzyl bromide 
• 106-43-4 para-chlorotoluene 
• 109-06-8 α-picoline 
• 106966-98-7 potassium 2-(pyridin-2-yl)acetate 

Downstream Products

• 109654-11-7 4-(pyridine-2-carbonyl)-benzoic acid 
• 40761-51-1 dimethyl-(3-[2]pyridyl-3-p-tolyl-propyl)-amine 
• 100-21-0 terephthalic acid 
• 20531-88-8 2-(4-methylbenzyl) pyridine 1-oxide 
• 29263-67-0 α-(4-methylphenyl)-2-pyridinemethanol 
• 78539-88-5 2-(4-toluoyl)pyridine 
• 1575656-61-9 2-phenyl-4-methylphenyl 2-pyridyl ketone 
• 1575656-79-9 C₂₅H₁₉NO 
• 782504-65-8 2-[(4-methylphenyl)methyl]piperidine hydrochloride 

Relevant articles and documents

Direct aerobic oxidation of 2-benzylpyridines in a gas-liquid continuous-flow regime using propylene carbonate as a solvent

The use of high-temperature/pressure gas-liquid continuous flow conditions dramatically enhances the iron-catalyzed aerobic oxidation of 2-benzylpyridines to their corresponding ketones. Pressurized air serves as a readily available oxygen source and propylene carbonate as a green solvent in this radically intensified preparation of synthetically valuable 2-aroylpyridines.

Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction

An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.

Metal-Free Halogen(I) Catalysts for the Oxidation of Aryl(heteroaryl)methanes to Ketones or Esters: Selectivity Control by Halogen Bonding

Metal-free halogen(I) catalysts were used for the selective oxidation of aryl(heteroaryl)methanes [C(sp3)?H] to ketones [C(sp2)=O] or esters [C(sp3)?O]. The synthesis of ketones was performed with a catalytic amount of NBS in DMSO solvent. Experimental studies and density functional theory (DFT) calculations supported the formation of halogen bonding (XB) between the heteroarene and N-bromosuccinimide, which enabled imine–enamine tautomerism of the substrates. No additional activator was required for this crucial step. Isotope-labeling and other supporting experiments suggested that a Kornblum-type oxidation with DMSO and aerobic oxygenation with molecular oxygen took place simultaneously. A background XB-assisted electron transfer between the heteroarenes and halogen(I) catalysts was responsible for the formation of heterobenzylic radicals and, thus, the aerobic oxygenation. For selective acyloxylation (ester formation), a catalytic amount of iodine was employed with tert-butyl hydroperoxide in aliphatic carboxylic acid solvent. Several control reactions, spectroscopic studies, and Time-Dependent Density Functional Theory (TD–DFT) calculations established the presence of acetyl hypoiodite as an active halogen(I) species in the acetoxylation process. With the help of a selectivity study, for the first time we report that the strength of the XB interaction and the frontier orbital mixing between the substrates and acyl hypoiodites determined the extent of the background electron-transfer process and, thus, the selectivity of the reaction.