4-(3-Pyridinyl)phenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-(3-Pyridinyl)phenylboronic acid pinacol ester
• CAS No.: 929203-04-3
• Molecular Formula: C17H20BNO2
• Molecular Weight: 281.162
• Hs Code.: 2934999090
• Mol file: 929203-04-3.mol

Synonyms:1-(3-Pyridyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;

Chemical Property of 4-(3-Pyridinyl)phenylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 410.7±28.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 31.35000
• Density: 1.09 g/cm³
• LogP: 3.04780
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(3-Pyridinyl)phenylboronic acid pinacol ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(3-Pyridinyl)phenylboronic acid pinacol ester

There total 17 articles about 4-(3-Pyridinyl)phenylboronic 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: 93.0%

3-(4-bromophenyl)pyridine (129013-83-8) + bis(pinacol)diborane (73183-34-3) → 3-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (929203-04-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; for 5h; Inert atmosphere; Reflux;

Reference yield: 91.0%

4-(3'-pyridinyl)-1-chlorobenzene (5957-97-1) + bis(pinacol)diborane (73183-34-3) → 3-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (929203-04-3)

Guidance literature:

With potassium acetate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; at 80 ℃; for 72h; Inert atmosphere;

DOI:10.1021/ol7030872

Reference yield: 87.0%

3-Bromopyridine (626-55-1,163928-56-1) + trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)stannane → 3-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (929203-04-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 12h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo402618r

upstream raw materials:

4-(3'-pyridinyl)-1-chlorobenzene

bis(pinacol)diborane

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

3-Bromopyridine

Downstream raw materials:

3,5,3',5'-tetra(p-pyridin-3-yl)phenyl-[1,1']biphenyl

C₄₄H₂₈N₂

1,3,5-tris[4-(pyridin-3-yl)phenyl]benzene

Refernces

• 1、 Dai, Hui-Xiong,Li, Hanyuan,Li, Ling-Jun,Liu, Qi-Sheng,Ma, Biao,Wang, Mei-Ling,Wang, Xing,Wang, Zhen-Yu,Xu, Hui. "Transformations of Aryl Ketones via Ligand-Promoted C?C Bond Activation". supporting information. p. 14388 - 14393. Retrieved 2020/07/06.
• 2、 Lee, Jiewon,Lee, Sunhee,Kim, Jin-Hyoung,Kang, Sang Ook,Han, Won-Sik. "Triaryl boron derivatives of pyridine as electron transporting materials for blue phosphorescent organic light-emitting diodes". . p. 5 - 11. Retrieved 2018/07/29.