63065-67-8

Basic information

• Product Name: 2-benzyl-5-methylpyridine
• Synonyms: 2-benzyl-5-methylpyridine;5-Methyl-2-(phenylmethyl)pyridine
• CAS NO: 63065-67-8
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.24902
• EINECS: 263-836-7
• Mol File: 63065-67-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 288.1°C at 760 mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 0.00414mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 2-benzyl-5-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-5-methylpyridine(63065-67-8)
• EPA Substance Registry System: 2-benzyl-5-methylpyridine(63065-67-8)

Safety Data

• Hazardous Substances Data: 63065-67-8(Hazardous Substances Data)

Usage

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

Upstream product

• 108-99-6 3-Methylpyridine 
• 100-44-7 benzyl chloride 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 62673-31-8 benzyl(bromo)zinc 
• 6921-34-2 benzylmagnesium chloride 
• 1003-73-2 3-picoline-N-oxide 
• 103-54-8 cinnamyl acetate 
• 18368-64-4 2-chloro-5-methylpyridine 
• 100-39-0 benzyl bromide 
• 16214-99-6 N-benzyl-3-methyl-pyridinium chloride 
• 80772-87-8 2-benzyl-5-methylpyridine 1-oxide 

Downstream Products

• 1416848-95-7 2-(2-(5-methylpyridin-2-yl)-1,2-diphenylethyl)malononitrile 
• 127581-43-5 (5-methylpyridin-2-yl)(phenyl)methanone 
• 80772-87-8 2-benzyl-5-methylpyridine 1-oxide 
• 233607-76-6 2(2,4-dinitrobenzyl)-5-methyl pyridine 

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.

A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS

A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.