20531-88-8

Basic information

• Product Name: 2-(4-methylbenzyl) pyridine 1-oxide
• Synonyms: 2-(4-methylbenzyl) pyridine 1-oxide
• CAS NO: 20531-88-8
• Molecular Weight: 199.252
• Mol File: 20531-88-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-(4-methylbenzyl) pyridine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylbenzyl) pyridine 1-oxide(20531-88-8)
• EPA Substance Registry System: 2-(4-methylbenzyl) pyridine 1-oxide(20531-88-8)

Safety Data

• Hazardous Substances Data: 20531-88-8(Hazardous Substances Data)

Upstream product

• 931-19-1 2-methylpyridine N-oxide 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 1201921-86-9 C₁₃H₂₁NO₂ 
• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 109-06-8 α-picoline 
• 29335-87-3 2-(4-methyl-benzyl)-pyridine 
• 694-59-7 pyridine N-oxide 
• 106-42-3 para-xylene 

Downstream Products

• 78539-88-5 2-(4-toluoyl)pyridine 
• 29335-87-3 2-(4-methyl-benzyl)-pyridine 
• 80772-76-5 3-methylpyrido<1,2-a>indole 

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.

Copper-Catalyzed Aerobic Oxygenation of Benzylpyridine N-Oxides and Subsequent Post-Functionalization

A copper-catalyzed aerobic oxidation of benzylpyridine N-oxides is reported. The N-oxide moiety acts as a built-in activator for the benzylic methylene oxidation, without requirement of additives. Reaction conditions were identified which suppress undesired benzoylpyridine formation via N-deoxygenation involving intermolecular oxygen transfer. The versatility of the N-oxide group of the benzoylpyridine N-oxide reaction products for post-functionalization of the pyridine ring is demonstrated through efficient C–C, C–N, C–O and C–Cl bond forming procedures, with both nucleophiles and electrophiles. Finally, the applicability of the new synthetic methodology is demonstrated in an alternative route towards the antihistaminic drug Acrivastine via three consecutive N-oxide activated C–H functionalization processes, starting from picoline N-oxide. (Figure presented.).

Palladium-catalyzed (N-oido-2-pyridinyl)methyl transfer from 2-(2-Hydroxyalkyl)pyridine N-oxide to aryl halides by β-carbon elimination

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