2-Bromobenzylboronic acid pinacol ester

Base Information

• Chemical Name: 2-Bromobenzylboronic acid pinacol ester
• CAS No.: 149989-79-7
• Molecular Formula: C13H18 B Br O2
• Molecular Weight: 297.00
• Hs Code.: 2934999090
• Mol file: 149989-79-7.mol

Synonyms:2-bromobenzylboronic acid pinacol ester;2-(2-Bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-Bromobenzylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 318 ºC
• Flash Point: 146 ºC
• PSA: 18.46000
• Density: 1.26
• LogP: 3.88940
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2-(2-Bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromobenzylboronic acid pinacol ester

There total 7 articles about 2-Bromobenzylboronic 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: 69.0%

1-Bromo-2-iodobenzene (583-55-1) + ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)zinc(II) iodide (129422-12-4) → 2-(2-bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149989-79-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; (N2), stirred for 3-5 h at 50°C, cooled to room temp.; diluted with benzene, washed with water and brine, dried over MgSO4;

DOI:10.1246/cl.1993.845

Reference yield: 66.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + 1-(2-bromobenzyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate → 2-(2-bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149989-79-7)

Guidance literature:

2,2'-bis(1,3,2-benzodioxaborole); 1-(2-bromobenzyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate; In N,N-dimethyl acetamide; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;

2,3-dimethyl-2,3-butane diol; With triethylamine; In N,N-dimethyl acetamide; at 20 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201804246

Reference yield: 63.0%

1-Bromo-2-iodobenzene (583-55-1) + C7H14BO2Zn(1+)*I(1-) → 2-(2-bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149989-79-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 50 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.organomet.1c00025

upstream raw materials:

((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)zinc(II) iodide

2,3-dibromobenzene

1-Bromo-2-iodobenzene

bis(pinacol)diborane