6-Chloropyridine-2-boronic acid pinacol ester

Base Information

• Chemical Name: 6-Chloropyridine-2-boronic acid pinacol ester
• CAS No.: 652148-92-0
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• Hs Code.: 2933399090
• Mol file: 652148-92-0.mol

Synonyms:2-Chloro-6-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)pyridine;

Chemical Property of 6-Chloropyridine-2-boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 0.000196mmHg at 25°C
• Melting Point: 107-110℃
• Refractive Index: 1.505
• Boiling Point: 338.2 °C at 760 mmHg
• PKA: -0.21±0.10(Predicted)
• Flash Point: 158.3 °C
• PSA: 31.35000
• Density: 1.14 g/cm³
• LogP: 2.03420
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

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

6-Chloropyridine-2-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Chloropyridine-2-boronic acid pinacol ester

There total 4 articles about 6-Chloropyridine-2-boronic 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: 38.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-bromo-6-chloro-pyridine (5140-72-7) → 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0)

Guidance literature:

2-bromo-6-chloro-pyridine; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran;

DOI:10.1016/j.tet.2003.10.020

Reference yield: 31.0%

2-bromo-6-chloro-pyridine (5140-72-7) + bis(pinacol)diborane (73183-34-3) → 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0)

Guidance literature:

With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate; In 1,4-dioxane; at 110 ℃; for 12h; chemoselective reaction;

DOI:10.1055/s-0036-1591549

Reference yield:

2,6-Dibromopyridine (626-05-1) → 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran / -78 °C

1.2: 67 percent / C₂Cl₆ / tetrahydrofuran / -78 - 20 °C

2.1: nBuLi / tetrahydrofuran / -78 °C

2.2: B(OiPr)3 / tetrahydrofuran / -78 - 20 °C

2.3: 38 percent / glacial acetic acid / tetrahydrofuran

With n-butyllithium; In tetrahydrofuran;

DOI:10.1016/j.tet.2003.10.020

upstream raw materials:

2,3-dimethyl-2,3-butane diol

2-bromo-6-chloro-pyridine

2,6-Dibromopyridine

bis(pinacol)diborane

Downstream raw materials:

2-chloro-6-(4-methylphenyl)pyridine

5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

2-chloro-6-phenyl-pyridine

6-Chloro-[2,2']bipyridinyl

Refernces

• 1、 Rao, Kanusu Umamaheswara,Venkateswarlu, Katta. "Pd II -Porphyrin Complexes - The First Use as Safer and Efficient Catalysts for Miyaura Borylation". supporting information. p. 1055 - 1060. Retrieved 2018/03/23.