3,5-Pridine diboronic acid pinacol ester

Base Information

• Chemical Name: 3,5-Pridine diboronic acid pinacol ester
• CAS No.: 1012085-50-5
• Molecular Formula: C17H27B2NO4
• Molecular Weight: 331.028
• Hs Code.: 2934999090
• Mol file: 1012085-50-5.mol

Synonyms:3,5-Pridine diboronic acid pinacol ester;3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property of 3,5-Pridine diboronic acid pinacol ester

Chemical Property:

• Boiling Point: 445.6±30.0 °C(Predicted)
• PKA: 5.21±0.24(Predicted)
• PSA: 49.81000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 1.68000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine

Technology Process of 3,5-Pridine diboronic acid pinacol ester

There total 3 articles about 3,5-Pridine diboronic acid pinacol ester 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: 79.0%

pyridine (110-86-1) + bis(pinacol)diborane (73183-34-3) → 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1012085-50-5) + 4-pyridineboronic acid pinacol ester (181219-01-2)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 60 ℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube;

pyridine; With C₃₂H₄₉AlBr₂O₂; In hexane; at 20 ℃; for 16h; Reagent/catalyst; Sealed tube;

DOI:10.1002/anie.201701238

Reference yield: 50.0%

pyridine (110-86-1) + bis(pinacol)diborane (73183-34-3) → 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1012085-50-5) + 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (329214-79-1)

Guidance literature:

bis(pinacol)diborane; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn; In toluene; at 20 ℃; for 0.5h; Schlenk technique;

pyridine; In toluene; at 70 ℃; for 24h; Reagent/catalyst; Solvent; Overall yield = > 99 percent; regioselective reaction; Catalytic behavior; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield:

pyridine (110-86-1) + bis(pinacol)diborane (73183-34-3) → 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1012085-50-5) + 4-pyridineboronic acid pinacol ester (181219-01-2) + 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (329214-79-1)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In para-xylene; at 20 ℃; for 0.5h; Schlenk technique;

pyridine; In para-xylene; at 80 ℃; for 24h; Reagent/catalyst; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

upstream raw materials:

pyridine

bis(pinacol)diborane

Downstream raw materials:

C₇₃H₄₉N₅

Refernces

• 1、 Yang, Lichen,Uemura, Nao,Nakao, Yoshiaki. "Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst". supporting information. p. 7972 - 7979. Retrieved 2019/05/22.