82226-09-3

Basic information

• Product Name: 2-Pyridinemethanol, 4-methyl-a-phenyl-
• CAS NO: 82226-09-3
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Mol File: 82226-09-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Pyridinemethanol, 4-methyl-a-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinemethanol, 4-methyl-a-phenyl-(82226-09-3)
• EPA Substance Registry System: 2-Pyridinemethanol, 4-methyl-a-phenyl-(82226-09-3)

Safety Data

• Hazardous Substances Data: 82226-09-3(Hazardous Substances Data)

Upstream product

• 108-89-4 picoline 
• 100-52-7 benzaldehyde 
• 4926-28-7 2-Bromo-4-picoline 
• 1003-67-4 4-methylpyridine-1-oxide 
• 5191-54-8 2-benzyl-4-methyl pyridine 
• 67-68-5 dimethyl sulfoxide 
• 108-86-1 bromobenzene 
• 1620-76-4 2-Cyano-4-methylpyridin 
• 18103-77-0 (4-methylpyridin-2-yl)(phenyl)methanone 
• 6630-33-7 ortho-bromobenzaldehyde 

Relevant articles and documents

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

Electrophilic reaction of N-Lewis acid and N-oxide Lewis acid complexes of 4-methylpyridines and their N-oxides through base-induced deprotonation

The comparative studies were carried out on the relative reactivity of4-methylpyridines, their N-oxides and their Lewis acid complexes towards electrophilic reaction. α-Deprotonation in pyridine ring rather than deprotonation of active methyl group or metal-halogen exchange occurred preferentially in the reaction of N- and N-oxides BF3 complexes with electrophile in the presence of LTMP-TMEDA in THF to give a -substituted-4-methylpyridines and their N-oxides.