5191-54-8

Basic information

• Product Name: 2-benzyl-4-methylpyridine
• Synonyms: 2-benzyl-4-methylpyridine
• CAS NO: 5191-54-8
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.24902
• EINECS: 225-975-1
• Mol File: 5191-54-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 289.6°C at 760 mmHg
• Flash Point: 120°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 0.00378mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 2-benzyl-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-4-methylpyridine(5191-54-8)
• EPA Substance Registry System: 2-benzyl-4-methylpyridine(5191-54-8)

Safety Data

• Hazardous Substances Data: 5191-54-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13N/c1-11-7-8-14-13(9-11)10-12-5-3-2-4-6-12/h2-9H,10H2,1H3

Upstream product

• 23662-66-0 1-benzyl-4-methylpyridinium chloride 
• 4926-28-7 2-Bromo-4-picoline 
• 100-39-0 benzyl bromide 
• 108-86-1 bromobenzene 
• 1251919-65-9 potassium 2-(4-methylpyridin-2-yl)acetate 
• 6921-34-2 benzylmagnesium chloride 
• 1003-67-4 4-methylpyridine-1-oxide 
• 770-09-2 benzyltrimethylsilane 
• 103-54-8 cinnamyl acetate 
• 78761-38-3 cinnamyl propionate 
• 108-47-4 2,4-lutidine 
• 100-68-5 methyl-phenyl-thioether 
• 67-56-1 methanol 
• 101-82-6 2-Benzylpyridine 

Downstream Products

• 1581709-76-3 4-methyl-2-(1-phenylvinyl)pyridine 
• 1581709-77-4 2-(1-phenylvinyl)-4-vinylpyridine 
• 80772-88-9 2-benzyl-4-methylpyridine 1-oxide 
• 82226-09-3 (4-methylpyridin-2-yl)-3-phenylmethanol 
• 25927-45-1 2-(2,4-dinitrobenzyl)-4-methylpyridine 
• 18164-96-0 2-benzoyl-isonicotinic acid 

Relevant articles and documents

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.

Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage

A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.