1267963-47-2

Basic information

• Product Name: 4-nitro-N-phenylpyridin-2-amine
• Synonyms: 4-nitro-N-phenylpyridin-2-amine
• CAS NO: 1267963-47-2
• Molecular Weight: 215.211
• Mol File: 1267963-47-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-nitro-N-phenylpyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitro-N-phenylpyridin-2-amine(1267963-47-2)
• EPA Substance Registry System: 4-nitro-N-phenylpyridin-2-amine(1267963-47-2)

Safety Data

• Hazardous Substances Data: 1267963-47-2(Hazardous Substances Data)

Upstream product

• 6945-67-1 2-bromo-4-nitropyridine 
• 62-53-3 aniline 

Relevant articles and documents

Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications

The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.