3-Hydroxy-4-nitrophenylboronic acid, pinacol ester

Base Information

• Chemical Name: 3-Hydroxy-4-nitrophenylboronic acid, pinacol ester
• CAS No.: 1339927-68-2
• Molecular Formula: C12H18BNO6
• Molecular Weight: 283.08542
• Hs Code.: 2931900090
• Mol file: 1339927-68-2.mol

Synonyms:3-Hydroxy-4-nitrophenylboronic acid, pinacol ester

Chemical Property of 3-Hydroxy-4-nitrophenylboronic acid, pinacol ester

Chemical Property:

• PSA: 84.51000
• LogP: 2.12280

Purity/Quality:

98% ^*data from raw suppliers

3-Hydroxy-4-nitrophenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Hydroxy-4-nitrophenylboronic acid, pinacol ester

There total 2 articles about 3-Hydroxy-4-nitrophenylboronic 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:

tetrabutylammonium 2‐nitrophenyl sulfate + bis(pinacol)diborane (73183-34-3) → 2‐nitro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenol + 2-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1339927-68-2)

Guidance literature:

tetrabutylammonium 2‐nitrophenyl sulfate; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; at 100 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In methanol; at 20 ℃; for 1h; Overall yield = 74 percent; Overall yield = 49 mg; regioselective reaction;

DOI:10.1021/jacs.9b07267

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) → 2‐nitro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenol + 2-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1339927-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; chlorosulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

2.2: 1 h / 20 °C

With chlorosulfonic acid; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jacs.9b07267

upstream raw materials:

bis(pinacol)diborane

2-hydroxynitrobenzene

Refernces