2-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol

Base Information

• Chemical Name: 2-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol
• CAS No.: 627906-52-9
• Molecular Formula: C13H19BO3
• Molecular Weight: 234.103
• Hs Code.: 2934999090
• Mol file: 627906-52-9.mol

Synonyms:4-Hydroxy-3-methylphenylboronic Acid Pinacol Ester;4-Hydroxy-3-methylbenzeneboronic acid pinacol ester;2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenol;Phenol, 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 2-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol

Chemical Property:

• Boiling Point: 351.0±35.0 °C(Predicted)
• PKA: 10.00±0.35(Predicted)
• PSA: 38.69000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 1.99980
• Storage Temp.: 2-8°C

Purity/Quality:

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

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol

There total 3 articles about 2-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol 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: 75.0%

4-Bromo-2-methylphenol (2362-12-1) + bis(pinacol)diborane (73183-34-3) → 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (627906-52-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 90 ℃; Inert atmosphere;

Reference yield:

ortho-cresol (95-48-7,77504-84-8) → 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (627906-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra-N-butylammonium tribromide / chloroform / 3 h / 20 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; tetra-N-butylammonium tribromide; In 1,4-dioxane; chloroform;

DOI:10.1016/j.tet.2012.04.106

Reference yield:

ortho-cresol (95-48-7,77504-84-8) → 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (627906-52-9) + 2-(3-hydroxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (331273-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; sulfur trioxide pyridine complex / dichloromethane / 19 h / 20 - 40 °C

1.2: 1 h

2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin / 1,4-dioxane / 36 h / 60 °C / Glovebox

2.2: 1 h / pH 1 - 2 / Glovebox

With pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; sulfur trioxide pyridine complex; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jacs.9b08464

upstream raw materials:

4-Bromo-2-methylphenol

bis(pinacol)diborane

ortho-cresol

Downstream raw materials:

(4-hydroxy-3-methylphenyl)boronic acid

2-{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylphenyl}-4,4,5,5-tetramethyl-1,3,2-dioxoborolane

HY-112667