2,6-DIFLUOROPYRIDINE-3-BORONIC ACID, PINACOL ESTER

Base Information

• Chemical Name: 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID, PINACOL ESTER
• CAS No.: 1072945-00-6
• Molecular Formula: C₁₁H₁₄BF₂NO₂
• Molecular Weight: 241.045
• Hs Code.: 2934999090
• Mol file: 1072945-00-6.mol

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

Chemical Property of 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID, PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0.00129mmHg at 25°C
• Melting Point: 50-53°C
• Refractive Index: 1.466
• Boiling Point: 307.8ºC at 760 mmHg
• Flash Point: 139.9ºC
• PSA: 31.35000
• Density: 1.16 g/cm³
• LogP: 1.65900

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,6-DIFLUOROPYRIDINE-3-BORONIC ACID, PINACOL ESTER

There total 2 articles about 2,6-DIFLUOROPYRIDINE-3-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: 50.8%

2,6-difluoro pyridine (1513-65-1) + bis(pinacol)diborane (73183-34-3) → 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1204333-58-3) + 2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1072945-00-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1021/acsmedchemlett.7b00258

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,6-difluoro pyridine (1513-65-1) → 2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1072945-00-6)

Guidance literature:

2,6-difluoro pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With Triisopropyl borate; acetic acid; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In tetrahydrofuran; hexane; at 20 ℃; for 3h; Inert atmosphere;

Reference yield:

2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1072945-00-6) → 4-(((3-chloro-4-fluorophenyl)imino)methyl)-2,6-difluoropyridin-3-ol

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 3 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

2.2: 3 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 0.5 h / -78 °C

4.1: trifluoroacetic acid / dichloromethane / 5 h / 0 - 20 °C

5.1: 2,2,2-trifluoroethanol; acetonitrile / 2 h / 20 °C

With n-butyllithium; sodium perborate tetrahydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; 2,2,2-trifluoroethanol; water; acetonitrile;

upstream raw materials:

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

2,6-difluoro pyridine

bis(pinacol)diborane

Downstream raw materials:

2,6-difluoro-3-hydroxypyridine

Refernces

• 1、 Takaya, Jun,Ito, Shisei,Nomoto, Hironori,Saito, Narumasa,Kirai, Naohiro,Iwasawa, Nobuharu. "Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex". supporting information. p. 17662 - 17665. Retrieved 2015/12/18.