5-Chloro-2-formylphenylboronic acid,pinacol ester

Base Information

• Chemical Name: 5-Chloro-2-formylphenylboronic acid,pinacol ester
• CAS No.: 1246633-36-2
• Molecular Formula: C₁₃H₁₆BClO₃
• Molecular Weight: 266.532
• Mol file: 1246633-36-2.mol

Synonyms:

Chemical Property of 5-Chloro-2-formylphenylboronic acid,pinacol ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Chloro-2-formylphenylboronic acid,pinacol ester

There total 4 articles about 5-Chloro-2-formylphenylboronic 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: 78.0%

(p-chlorobenzylidene)(tert-butyl)amine (943-72-6,86402-00-8) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde (1246633-36-2)

Guidance literature:

With 8-amino quinoline; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 90 ℃; for 12h; Glovebox;

DOI:10.1021/jacs.5b11683

Reference yield: 55.0%

2-bromo-4-chlorobenzaldehyde (84459-33-6) + bis(pinacol)diborane (73183-34-3) → 4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde (1246633-36-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

Reference yield:

(p-chlorobenzylidene)(tert-butyl)amine (943-72-6,86402-00-8) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C13H16BClO3 (1112209-14-9) + 4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde (1246633-36-2)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; at 90 ℃; for 12h; Reagent/catalyst; Overall yield = 76 %; Glovebox;

DOI:10.1021/jacs.5b11683

upstream raw materials:

4-chlorobenzaldehyde

(p-chlorobenzylidene)(tert-butyl)amine

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

(2-formyl-5-chlorophenyl)boronic acid

Refernces

• 1、 Yan, Yu-Hang,Li, Zhao-Feng,Ning, Xiang-Li,Deng, Ji,Yu, Jun-Lin,Luo, Yubin,Wang, Zhenling,Li, Guo,Li, Guo-Bo,Xiao, You-Cai. "Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases". supporting information. . Retrieved 2021/04/12.
• 2、 -. "SUBSTITUTED HETEROCYCLIC COMPOUNDS AS ALLOSTERIC MODULATORS OF GROUP II METABOTROPIC GLUTAMATE RECEPTORS". Page/Page column 217; 218. . Retrieved 2018/12/03.