2-FLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-FLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER
• CAS No.: 458532-86-0
• Molecular Formula: C₁₁H₁₅BFNO₂
• Molecular Weight: 223.055
• Hs Code.: 2933399090
• Mol file: 458532-86-0.mol

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

Chemical Property of 2-FLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0.000994mmHg at 25°C
• Melting Point: 48-52℃
• Refractive Index: 1.477
• Boiling Point: 312.1 °C at 760 mmHg
• PKA: -1.27±0.10(Predicted)
• Flash Point: 142.5 °C
• PSA: 31.35000
• Density: 1.09 g/cm³
• LogP: 1.51990
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

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

2-Fluoropyridine-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used in pharmaceuticals, agrochemicals, and high-tech materials.

Technology Process of 2-FLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER

There total 6 articles about 2-FLUOROPYRIDINE-4-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: 99.1%

4-bromo-2-fluoropyridine (128071-98-7) + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-86-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 100 ℃; for 12h;

Reference yield: 81.0%

2-fluoropyridine (372-48-5) + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-86-0)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 60 ℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube;

2-fluoropyridine; With C₃₂H₄₉AlBr₂O₂; In hexane; at 20 ℃; for 6h; Sealed tube;

DOI:10.1002/anie.201701238

Reference yield: 70.0%

boric acid tributyl ester (688-74-4) + 2-fluoro-4-iodopyridine (22282-70-8) → 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-86-0)

Guidance literature:

2-fluoro-4-iodopyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 2h;

boric acid tributyl ester; In diethyl ether; at -78 - 20 ℃; for 3h;

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

upstream raw materials:

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

4-bromo-2-fluoropyridine

boric acid tributyl ester

2-fluoro-4-iodopyridine

Downstream raw materials:

6-(2-fluoro-4-pyridyl)pyrido[3,2-d]pyrimidin-4-amine

Refernces

• 1、 Yang, Lichen,Semba, Kazuhiko,Nakao, Yoshiaki. "para-Selective C?H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis". supporting information. p. 4853 - 4857. Retrieved 2017/04/11.
• 2、 Sadler, Scott A.,Tajuddin, Hazmi,Mkhalid, Ibraheem A. I.,Batsanov, Andrei S.,Albesa-Jove, David,Cheung, Man Sing,Maxwell, Aoife C.,Shukla, Lena,Roberts, Bryan,Blakemore, David C.,Lin, Zhenyang,Marder, Todd B.,Steel, Patrick G.. "Iridium-catalyzed C-H borylation of pyridines". supporting information. p. 7318 - 7327. Retrieved 2014/11/07.