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

Base Information

• Chemical Name: 2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 652148-92-0
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• Hs Code.: 2933399090
• European Community (EC) Number: 640-239-3
• DSSTox Substance ID: DTXSID30590540
• Nikkaji Number: J1.983.519G
• Wikidata: Q72458427
• Mol file: 652148-92-0.mol

Synonyms:652148-92-0;6-Chloropyridine-2-boronic acid pinacol ester;2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-chloro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;MFCD06798259;2-Chloro-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;Pyridine, 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL201979;(6-CHLOROPYRIDIN-2-YL)BORONIC ACID PINACOL ESTER;DTXSID30590540;CROJXBLQCOIOBI-UHFFFAOYSA-N;BCP21543;BBL100789;STL554583;AKOS005255640;PB29406;CS-10668;SY009368;DB-032270;6-chloropyridin-2-boronic acid pinacol ester;EN300-212582;A835020;J-508895;2-chloranyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property of 2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.0884366
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

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:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=NC(=CC=C2)Cl

Technology Process of 2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 4 articles about 2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

6-Chloro-[2,2']bipyridinyl

2-chloro-6-phenyl-pyridine

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