2-(2,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 408492-25-1
• Molecular Formula: C12H15BF2O2
• Molecular Weight: 240.05400
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60581481
• Nikkaji Number: J1.689.011A
• Wikidata: Q82472641
• Mol file: 408492-25-1.mol

Synonyms:408492-25-1;2-(2,5-DIFLUOROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2,5-DIFLUOROPHENYLBORONIC ACID PINACOL ESTER;2,5-DIFLUOROBENZENEBORONIC ACID PINACOL ESTER;SCHEMBL14274295;DTXSID60581481;MFCD12405346;AKOS017550067;MB11838;AS-55703;CS-0061089;W17812;EN300-1425736

Chemical Property of 2-(2,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• PSA: 18.46000
• LogP: 2.26400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 240.1133162
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

98.5% ^*data from raw suppliers

2,5-Difluorophenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-(2,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 12 articles about 2-(2,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 87.0%

2-bromo-1,4-difluorobenzene (399-94-0) + bis(pinacol)diborane (73183-34-3) → 2-(2,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-25-1)

Guidance literature:

2-bromo-1,4-difluorobenzene; With potassium acetate; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

bis(pinacol)diborane; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1039/c8tc06517a

Reference yield: 85.0%

para-difluorobenzene (540-36-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-25-1)

Guidance literature:

[Ir(hydrotris(pyrazolyl)borate)Ir(1,5-cyclooctadiene)]; In neat (no solvent); Ir catalyst was added to Schlenk tube; evacuated; backfilled with N2; arene and pinacolborane were added; stirred at 120°C for 18 h; extd. (ether); washed (brine); dried (Na2SO4); concd.; distd.;

DOI:10.1246/bcsj.79.1980

Reference yield: 85.0%

para-difluorobenzene (540-36-3) + 4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(2,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-25-1)

Guidance literature:

iridium(hydrotris(pyrazolyl)borate)(1,5-cyclooctadiene); at 120 ℃; for 16h;

DOI:10.1246/bcsj.79.1980

upstream raw materials:

para-difluorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

1-chloro-2,5-difluorobenzene

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

Downstream raw materials:

2,5-difluorobenzophenone

1,4-difluoro-2,5-di(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)benzene

Refernces

• 1、 Liu, Zhiqiang,Budiman, Yudha P.,Tian, Ya-Ming,Friedrich, Alexandra,Huang, Mingming,Westcott, Stephen A.,Radius, Udo,Marder, Todd B.. "Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes". supporting information. p. 17267 - 17274. Retrieved 2020/12/01.
• 2、 -. "Nitrogen-containing heterocyclic compound and application thereof and organic electroluminescent device (by machine translation)". Paragraph 0077-0081. . Retrieved 2019/11/25.