2,2'-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Base Information

• Chemical Name: 2,2'-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• CAS No.: 303006-90-8
• Molecular Formula: C18H26B2F2O4
• Molecular Weight: 366.021
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID801139755
• Nikkaji Number: J1.429.353A
• Mol file: 303006-90-8.mol

Synonyms:303006-90-8;2,2'-(2,5-DIFLUORO-1,4-PHENYLENE)BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE);2,5-DIFLUORO-1,4-PHENYLENEDIBORONIC ACID, PINACOL ESTER;2-[2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2,2'-(2,5-Difluoro-1,4-phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane];SCHEMBL1646761;DTXSID801139755;MFCD12407211;AKOS025293582;AS-73607;CS-0175505;C15528;2,5-Difluoro-1,4-phenylenediboronic acid pinacol ester;1,3,2-Dioxaborolane, 2,2'-(2,5-difluoro-1,4-phenylene)bis[4,4,5,5-tetramethyl-;2,2'-(2,5-Difluoro-p-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);2,2-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Chemical Property of 2,2'-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Chemical Property:

• Melting Point: 202-205℃
• Boiling Point: 419.6±45.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 2.56320
• Storage Temp.: Room temperature.
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 366.1985260
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

97% ^*data from raw suppliers

2,5-Difluoro-1,4-phenylenediboronicacid,pinacolester ^*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=CC(=C(C=C2F)B3OC(C(O3)(C)C)(C)C)F

Technology Process of 2,2'-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

There total 5 articles about 2,2'-(2,5-Difluoro-1,4-phenylene)bis(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: 74.1%

1,4-dibromo-2,5-difluorobenzene (327-51-5) + bis(pinacol)diborane (73183-34-3) → 1,4-difluoro-2,5-di(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)benzene (303006-90-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 24h; Inert atmosphere;

Reference yield: 39.0%

1,4-dibromo-2,5-difluorobenzene (327-51-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1,4-difluoro-2,5-di(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)benzene (303006-90-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; for 15h;

DOI:10.1021/ja000759a

Reference yield: 32.0%

1,2,4,5-Tetrafluorobenzene (327-54-8) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2,4,5-trifluorophenyl)-1,3,2-dioxaborolane + 1,4-difluoro-2,5-di(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)benzene (303006-90-8)

Guidance literature:

With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel⁽⁰⁾; C₃₂H₄₁O₆P₂Rh; cesium fluoride; In 1,3,5-trimethyl-benzene; at 25 ℃; for 6h; regioselective reaction; Irradiation; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.8b09790

upstream raw materials:

1,4-dibromo-2,5-difluorobenzene

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

bis(pinacol)diborane

1,2,4,5-Tetrafluorobenzene

Downstream raw materials:

2-{4-[8-(2,5-dimethoxy-phenyl)-naphthalen-1-yl]-2,5-difluoro-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

C₃₄H₂₃F₂IO₂