18103-77-0

Basic information

• Product Name: Methanone, (4-methyl-2-pyridinyl)phenyl-
• CAS NO: 18103-77-0
• Molecular Formula: C13H11NO
• Molecular Weight: 197.236
• Mol File: 18103-77-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Methanone, (4-methyl-2-pyridinyl)phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-methyl-2-pyridinyl)phenyl-(18103-77-0)
• EPA Substance Registry System: Methanone, (4-methyl-2-pyridinyl)phenyl-(18103-77-0)

Safety Data

• Hazardous Substances Data: 18103-77-0(Hazardous Substances Data)

Upstream product

• 108-89-4 picoline 
• 93-89-0 benzoic acid ethyl ester 
• 1003-67-4 4-methylpyridine-1-oxide 
• 10364-94-0 1-benzoylimidazole 
• 501-65-5 diphenyl acetylene 
• 536-74-3 phenylacetylene 
• 1620-76-4 2-Cyano-4-methylpyridin 
• 108-86-1 bromobenzene 
• 611-74-5 N,N-dimethylbenzamide 

Downstream Products

• 58088-62-3 C-(4-methyl-pyridin-2-yl)-C-phenyl-methylamine 
• 58088-24-7 (4-methyl-pyridin-2-yl)-phenyl-methanone oxime 
• 82226-09-3 (4-methylpyridin-2-yl)-3-phenylmethanol 

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.

Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation

A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.

Iridium-Catalyzed Highly Enantioselective Transfer Hydrogenation of Aryl N-Heteroaryl Ketones with N-Oxide as a Removable ortho-Substituent

A highly enantioselective transfer hydrogenation of non-ortho-substituted aryl N-heteroaryl ketones, using readily available chiral diamine-derived iridium complex (S,S)-1f as a catalyst and sodium formate as a hydrogen source in a mixture of H2O/i-PrOH (v/v = 1:1) under ambient conditions, is described. The chiral aryl N-heteroaryl methanols were obtained with up to 98.2% ee by introducing an N-oxide as a removable ortho-substituent. In contrast, no more than 15.1% ee was observed in the absence of an N-oxide moiety. Furthermore, the practical utility of this protocol was also demonstrated by gram-scale asymmetric synthesis of bepotastine besilate in 51% total yield and 99.9% ee.