R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol

Base Information

• Chemical Name: R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol
• CAS No.: 127049-50-7
• Molecular Formula: C20H28N2O2
• Molecular Weight: 328.455
• Mol file: 127049-50-7.mol

Synonyms:R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol;(αR,α'R)-α,α'-Bis(tert-butyl)-[2,2'-bipyridine]-6,6'- dimethanol

Chemical Property of R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol

Chemical Property:

• Boiling Point: 473.0±45.0 °C(Predicted)
• PKA: 13.02±0.20(Predicted)
• PSA: 66.24000
• Density: 1.085±0.06 g/cm3(Predicted)
• LogP: 4.30260

Purity/Quality:

98.5% ^*data from raw suppliers

Bolm'sligand ≥97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol

There total 8 articles about R,R-α,α'-bis(1,1-diMethylethyl)-[2,2'-Bipyridine]-6,6'-diMethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

(R)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropanol (127912-58-7) → (R,R)-6,6'-bis-(1-hydroxy-2,2-dimethylpropyl)-2,2'-bipyridine (127049-50-7)

Guidance literature:

With triphenylphosphine; nickel dichloride; zinc; In N,N-dimethyl-formamide; at 72 ℃; for 3.5h;

Reference yield:

(rac)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-ol (127127-27-9) → (meso)-1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(2,2-dimethylpropan-1-ol) (127127-29-1) + (rac)-1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(2,2-dimethylpropan-1-ol) (127049-50-7,127127-28-0,127127-29-1,131726-65-3)

Guidance literature:

Reference yield:

1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-one (127049-48-3) → (meso)-1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(2,2-dimethylpropan-1-ol) (127127-29-1) + (rac)-1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(2,2-dimethylpropan-1-ol) (127049-50-7,127127-28-0,127127-29-1,131726-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 2 h / 20 °C

2: bis(benzonitrile)palladium(II) dichloride; Tetrakis(dimethylamino)ethylen / N,N-dimethyl-formamide / 28 h / 50 °C / Inert atmosphere

With sodium tetrahydroborate; bis(benzonitrile)palladium(II) dichloride; Tetrakis(dimethylamino)ethylen; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/adsc.201800452

upstream raw materials:

(R)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropanol

Methyl pivalate

(rac)-1-(6-bromopyridin-2-yl)-2,2-dimethylpropan-1-ol

2,6-Dibromopyridine

Downstream raw materials:

(1R,2R)-1,2-diphenyl-2-(phenylamino)ethanol

(1S,2S)-1,2-diphenyl-2-(phenylamino)ethanol

Refernces

• 1、 -. "PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYLATED COMPOUNDS". Page/Page column title page; 5; 9. . Retrieved 2010/11/24.
• 2、 Bolm, Carsten,Zehnder, Margareta,Bur, Daniel. "Optisch aktive Bipyridine in der asymmetrischen Katalyse". . p. 206 - 208. Retrieved 2007/10/02.