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

Base Information

• Chemical Name: 2-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 452972-14-4
• Molecular Formula: C11H15BFNO2
• Molecular Weight: 223.055
• Hs Code.: 2933399090
• European Community (EC) Number: 670-324-0
• DSSTox Substance ID: DTXSID40476866
• Nikkaji Number: J3.545.257E
• Wikidata: Q72476726
• Mol file: 452972-14-4.mol

Synonyms:452972-14-4;2-Fluoropyridine-3-boronic acid pinacol ester;2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Fluoropyridine-3-boronic acid, pinacol ester;MFCD06798245;2-fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;PYRIDINE, 2-FLUORO-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;SCHEMBL2813914;(2-FLUOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;DTXSID40476866;2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine;AKOS005173604;AB29851;BS-2069;CS-W003352;SY023546;AM20051193;F1105;FT-0684404;A22250;EN300-1587529;J-509524;2-(2-Fluoro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Vapor Pressure: 0.00113mmHg at 25°C
• Melting Point: 42-45 °C
• Refractive Index: 1.477
• Boiling Point: 309.9 °C at 760 mmHg
• PKA: -0.44±0.12(Predicted)
• Flash Point: 141.2 °C
• PSA: 31.35000
• Density: 1.1 g/cm³
• LogP: 1.51990
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 223.1179870
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

98% ^*data from raw suppliers

2-Fluoropyridine-3-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(N=CC=C2)F
• Uses: 2-Fluoropyridine-3-boronic acid, pinacol ester

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

There total 10 articles about 2-Fluoro-3-(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: 58.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-fluoropyridine (372-48-5) → 2-[3-(2-fluoro)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (452972-14-4)

Guidance literature:

2-fluoropyridine; With lithium diisopropyl amide; In diethyl ether; at -60 ℃; for 0.75h;

With Triisopropyl borate; In diethyl ether; at -60 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00283-1

Reference yield: 34.0%

2-fluoropyridine (372-48-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[3-(2-fluoro)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (452972-14-4)

Guidance literature:

2-fluoropyridine; With n-butyllithium; diisopropylamine; In diethyl ether; at -60 ℃; for 1.5h; Inert atmosphere;

With Triisopropyl borate; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With acetic acid; In diethyl ether; at 20 ℃; Inert atmosphere;

Reference yield: 34.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-fluoropyridine (372-48-5) + Triisopropyl borate (5419-55-6) → 2-[3-(2-fluoro)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (452972-14-4)

Guidance literature:

2-fluoropyridine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; diethyl ether; at -60 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; diethyl ether; at -60 - 20 ℃; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran; diethyl ether; at 20 ℃; Inert atmosphere;

upstream raw materials:

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

2-fluoropyridine

(2-fluoro-pyridin-3-yl)boronic acid

Triisopropyl borate

Downstream raw materials:

3-(3-chloro-phenyl)-2-fluoro-pyridine

(R)-2-fluoro-3-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)pyridine

(S)-1-(2-fluoropyridin-3-yl)-1-phenylethanol

(R)-2-fluoro-3-(1-phenylethyl)pyridine

Refernces

• 1、 -. "Indazole Compounds as IRAK4 Inhibitors". Paragraph 0173. . Retrieved 2016/11/28.
• 2、 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.