1451255-09-6

Basic information

• Product Name: N-tert-butyl-N-phenyl-2,2′-bipyridin-6-amine
• CAS NO: 1451255-09-6
• Molecular Weight: 303.407
• Mol File: 1451255-09-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-tert-butyl-N-phenyl-2,2′-bipyridin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butyl-N-phenyl-2,2′-bipyridin-6-amine(1451255-09-6)
• EPA Substance Registry System: N-tert-butyl-N-phenyl-2,2′-bipyridin-6-amine(1451255-09-6)

Safety Data

• Hazardous Substances Data: 1451255-09-6(Hazardous Substances Data)

Upstream product

• 937-33-7 N-tert-butylaniline 
• 626-05-1 2,6-Dibromopyridine 
• 109-04-6 2-bromo-pyridine 
• 1451255-08-5 6-bromo-N-tert-butyl-N-phenylpyridin-2-amine 

Downstream Products

• 1451255-10-9 C₂₆H₁₉N₃OPt 

Relevant articles and documents

Reaction of N -isopropyl- N -phenyl-2,2′-bipyridin-6-amine with K2PtCl4: Selective C-H bond activation, C-N bond cleavage, and selective acylation

The selective C-H bond activation of N-isopropyl-N-phenyl-2,2′- bipyridin-6-amine promoted by Pt(II) was complicated by the low selectivity of sp2 C-H bond activation in acetonitrile and low yield of sp 3 C-H activation in acetic acid. The use of a base was found to effectively suppress the competing sp3 C-H bond activation in acetonitrile, improving the selectivity of sp2 C-H bond activation from 70% to 99%. In the reaction in acetic acid, the low yield was due to the competing C-N bond cleavage. The use of a base reduced the C-N bond cleavage, but not completely. The reaction of N-tert-butyl-N-phenyl-2,2′-bipyridin- 6-amine with K2PtCl4 in acetic acid produced the cyclometalated complex with complete C-N bond cleavage and its acylated derivative. These results indicated that the C-N bond cleavage might proceed via heterolytic C-N bond dissociation. The acylation following the C-N cleavage in the reaction in acetic acid is regioselective. Further experiments showed that the reaction of N-phenyl-2,2′-bipyridin-6-amine with K 2PtCl4 in acetic acid produced the cyclometalated complex, while the reaction in a mixture of acetic anhydride and acetic acid produced the acylated cyclometalated complex. An X-ray crystal structure study revealed strong intramolecular H bonding in the acylated complexes. The regioselectivity was explained in terms of H bonding and the electron distribution predicted by the DFT calculations.