2-Chloro-3-(hydroxyMethyl)phenylboronic Acid Pinacol Ester

Base Information

• Chemical Name: 2-Chloro-3-(hydroxyMethyl)phenylboronic Acid Pinacol Ester
• CAS No.: 1400755-07-8
• Molecular Formula: C13H20BClO4
• Molecular Weight: 286.5595
• Mol file: 1400755-07-8.mol

Synonyms:2-Chloro-3-(hydroxyMethyl)phenylboronic Acid Pinacol Ester;2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol

Chemical Property of 2-Chloro-3-(hydroxyMethyl)phenylboronic Acid Pinacol Ester

Chemical Property:

• Boiling Point: 391.6±37.0 °C(Predicted)
• PKA: 14.03±0.10(Predicted)
• PSA: 38.69000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 2.13150
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2-Chloro-3-(Hydroxymethyl)PhenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Chloro-3-(hydroxyMethyl)phenylboronic Acid Pinacol Ester

There total 2 articles about 2-Chloro-3-(hydroxyMethyl)phenylboronic 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: 82.0%

(3-bromo-2-chloro-phenyl)methanol (1261524-75-7) + bis(pinacol)diborane (73183-34-3) → [2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1400755-07-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2017.09.036

Reference yield:

3-bromo-2-chloro-benzoic acid (56961-27-4) → [2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1400755-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / Reflux

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; dimethylsulfide borane complex; potassium acetate; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

[2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1400755-07-8) → 5-((4-chloro-5-((2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)-2-formylphenoxy)methyl)nicotinonitrile

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Sealed tube

With di-isopropyl azodicarboxylate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

(3-bromo-2-chloro-phenyl)methanol

bis(pinacol)diborane

3-bromo-2-chloro-benzoic acid

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