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

Base Information

• Chemical Name: 2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 444120-95-0
• Molecular Formula: C11H15BFNO2
• Molecular Weight: 223.055
• Hs Code.: 2934999090
• European Community (EC) Number: 626-822-5
• DSSTox Substance ID: DTXSID20479299
• Wikidata: Q72476734
• Mol file: 444120-95-0.mol

Synonyms:444120-95-0;2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Fluoropyridine-5-boronic acid pinacol ester;6-Fluoropyridine-3-boronic acid, pinacol ester;6-FLUOROPYRIDINE-3-BORONIC ACID PINACOL ESTER;2-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Flouropyridine-5-boronic acid pinacol ester;MFCD03412792;(6-FLUOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;Pyridine, 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL484154;DTXSID20479299;ZKSRQMCKFLGPQU-UHFFFAOYSA-N;AKOS016011501;CS-W013102;HY-W012386;PB14350;DS-13640;SY024947;AM20051186;F1094;FT-0766369;A25322;ADENOSINE-8(3)H3,5-CYCLICMONOPHOSPHATE;EN300-318544;2-Fluoropyridine-5-boronic acid pinacol ester, >=95%;2-FLUORO-5-(4 4 5 5-TETRAMETHYL-(1 3 2)&;2-(6-Fluoro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-pyridine;2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)pyridine;2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 29-33oC(lit.)
• Boiling Point: 304.208oC at 760 mmHg
• PKA: -0.44±0.12(Predicted)
• Flash Point: >230 °F
• PSA: 31.35000
• Density: 1.1g/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%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)F

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

There total 2 articles about 2-Fluoro-5-(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: 11.0%

2-fluoropyridine (372-48-5) + bis(pinacol)diborane (73183-34-3) → C17H26B2FNO4 + C17H26B2FNO4 + 2-[3-(2-fluoro)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (452972-14-4) + 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-86-0) + 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-95-0)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; at 20 ℃; for 24h; regioselective reaction; Glovebox; Sealed tube;

DOI:10.1039/c4ob01565g

Reference yield:

2-fluoropyridine (372-48-5) + bis(pinacol)diborane (73183-34-3) → 2-[3-(2-fluoro)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (452972-14-4) + 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-86-0) + 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-95-0)

Guidance literature:

With n-butyllithium; C₂₈H₄₁ClNPPtSi; In hexane; 1,3,5-trimethyl-benzene; at 20 - 150 ℃; for 4h; Overall yield = 86 %; Overall yield = 77.4 mg; regioselective reaction; Inert atmosphere;

DOI:10.1039/c5cc07263h

Reference yield: 93.0%

1,3-bis(3-pyridinephenyl)-5-(3-bromophenyl)benzene (1165939-26-3) + 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-95-0) → C39H26FN3 (1197989-76-6)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 20h; Inert atmosphere; Reflux;

upstream raw materials:

2-fluoropyridine

bis(pinacol)diborane

Downstream raw materials:

2-fluoro-5-(4-methoxyphenyl)pyridine

6-fluoropyridin-3-ol

C₃₉H₂₆FN₃

N-{3-[4-(6-fluoropyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide

Refernces

• 1、 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.