58414-96-3

Basic information

• Product Name: Pyridine, 2-[[(4-methylphenyl)sulfonyl]methyl]-
• Synonyms: 4-methylphenyl 2-pyridinylmethyl sulfone;2-{[(4-methylphenyl)sulfonyl]methyl}pyridine
• CAS NO: 58414-96-3
• Molecular Formula: C₁₃H₁₃NO₂S
• Molecular Weight: 247.31282
• Mol File: 58414-96-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyridine, 2-[[(4-methylphenyl)sulfonyl]methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-[[(4-methylphenyl)sulfonyl]methyl]-(58414-96-3)
• EPA Substance Registry System: Pyridine, 2-[[(4-methylphenyl)sulfonyl]methyl]-(58414-96-3)

Safety Data

• Hazardous Substances Data: 58414-96-3(Hazardous Substances Data)

Upstream product

• 22353-29-3 4-methyl-N'-(pyridin-2-ylmethylene)benzenesulfonohydrazide 
• 33984-18-8 2-<(4-methylphenyl)thiomethyl>-pyridine 
• 109-04-6 2-bromo-pyridine 
• 3185-99-7 Methyl p-tolyl sulfone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 4377-33-7 2-chloromethylpyridine 

Downstream Products

• 137890-00-7 2-Chloro-10-(toluene-4-sulfonyl)-pyrimido[4,5-b]indolizine 
• 137890-01-8 2-Methylsulfanyl-10-(toluene-4-sulfonyl)-pyrimido[4,5-b]indolizine 
• 300395-91-9 C₁₃H₁₃NO₃S 

Relevant articles and documents

Palladium Catalyzed Monoselective α-Arylation of Sulfones and Sulfonamides with 2,2,6,6-Tetramethylpiperidine·ZnCl·LiCl Base and Aryl Bromides

A palladium catalyzed Negishi-type α-arylation of sulfones and sulfonamides with a broad range of aryl bromides has been developed. The substrates are selectively metalated in situ with tmp·ZnCl·LiCl base (tmp: 2,2,6,6-tetramethylpiperidine) and cross-coupled in the presence of a catalyst system that is generated from Pd(dba)2 and XPhos. Electron-deficient, electron-rich, and heterocyclic aryl bromides have been successfully cross-coupled, and sensitive functional groups are well tolerated. Simple aryl bromides are converted overnight at 60 °C in THF while heteroaryl bromides are efficiently coupled within 2 h at 130 °C in a microwave reactor. The desired monoarylated α-branched benzyl sulfones and sulfonamides were obtained in good yields, and overarylation was not detected. The procedure is ideal for late stage functionalization in parallel medicinal chemistry.

Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions

A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.