4-(Hydroxymethyl)-3-methylphenylboronic Acid Pinacol Ester

Base Information

• Chemical Name: 4-(Hydroxymethyl)-3-methylphenylboronic Acid Pinacol Ester
• CAS No.: 1160430-87-4
• Molecular Formula: C14H21BO3
• Molecular Weight: 248.13
• Hs Code.: 2934999090
• Mol file: 1160430-87-4.mol

Synonyms:4-(Hydroxymethyl)-3-methylphenylboronic Acid Pinacol Ester;2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol;(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Chemical Property of 4-(Hydroxymethyl)-3-methylphenylboronic Acid Pinacol Ester

Chemical Property:

• PSA: 38.69000
• LogP: 1.78650

Purity/Quality:

97% ^*data from raw suppliers

4-(Hydroxymethyl)-3-methylphenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(Hydroxymethyl)-3-methylphenylboronic Acid Pinacol Ester

There total 2 articles about 4-(Hydroxymethyl)-3-methylphenylboronic 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: 90.0%

4-bromo-2-methylbenzyl alcohol (17100-58-2) + bis(pinacol)diborane (73183-34-3) → (2‐methyl‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)methanol (1160430-87-4)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; for 4h; Heating / reflux;

Reference yield:

2-methyl-benzyl alcohol (89-95-2) → (2‐methyl‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)methanol (1160430-87-4) + [2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1544673-46-2)

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 / 12 h / 40 °C / Glovebox

2.2: 1 h / 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

Reference yield: 81.0%

(2‐methyl‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)methanol (1160430-87-4) → 2-[4-(bromomethyl)-3-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1160431-16-2)

Guidance literature:

With phosphorus tribromide; In dichloromethane; at 0 ℃;

upstream raw materials:

4-bromo-2-methylbenzyl alcohol

bis(pinacol)diborane

2-methyl-benzyl alcohol

Downstream raw materials:

{4-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-2-methylphenyl}methanol

2-[4-(bromomethyl)-3-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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