131726-65-3

Basic information

• Product Name: S,S-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol
• Synonyms: S,S-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol;(αS,α'S)-α,α'-Bis(tert-butyl)-[2,2'-bipyridine]-6,6'- dimethanol
• CAS NO: 131726-65-3
• Molecular Weight: 328.455
• Mol File: 131726-65-3.mol

Chemical Properties

• CAS DataBase Reference: S,S-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol(CAS DataBase Reference)
• NIST Chemistry Reference: S,S-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol(131726-65-3)
• EPA Substance Registry System: S,S-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol(131726-65-3)

Safety Data

• Hazardous Substances Data: 131726-65-3(Hazardous Substances Data)

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 630-18-2 tert-butyl isocyanide 
• 127049-48-3 1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-one 
• 630-19-3 pivalaldehyde 
• 127127-27-9 (rac)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-ol 
• 127049-52-9 (S)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-ol 

Relevant articles and documents

Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).

New efficient method for the synthesis of chiral 2,2′-bipyridyl ligands

An efficient preparation of chiral 2,2′-bipyridines was developed. Compound 1 was synthesized in 54% yield for three steps starting from 2,6-dibromopyridine. In this synthesis, only catalytic amounts of metals were used in the asymmetric reduction and homo-coupling reaction steps. The total yield and simplicity of experimental procedures were much improved compared with those of the previous report. Other chiral 2,2′-bipyridines were similarly synthesized with high efficiency. Georg Thieme Verlag Stuttgart.

Enantioselective Synthesis of Optically Active Pyridine Derivatives and C2-Symmetric 2,2'-Bipyridines

Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11-13, 24, and 25 using the chiral borane reagent chlorodiisopinocampherylborane .Nickel(0)-mediated coupling of bromopyridines 2, 15, and 31 gives C2-symmetric 2,2'-bipyridines (R,R)-32, (R,R)-33, and (S,S)-38, respectively, which form metal complexex with Co(II), Pd(II), Cu(I), and Ag(I).Aryl-substituted pyridines 26, and 39-41 are synthesized by palladium(0)-catalized cross coupling of 2 and 15 with boronic acids 42-44.Key Words: 2,2-Bipyridines / Pyridines, optically active / Chiral ligands / Asymmetric Synthesis / Catalysis, enantioselective