4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl

Base Information

• Chemical Name: 4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl
• CAS No.: 207611-87-8
• Molecular Formula: C24H32B2O4
• Molecular Weight: 406.13
• Hs Code.: 29319090
• European Community (EC) Number: 805-574-3
• DSSTox Substance ID: DTXSID70441269
• Nikkaji Number: J1.898.307I
• Wikidata: Q72443696
• Mol file: 207611-87-8.mol

Synonyms:207611-87-8;4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl;4,4'-BIPHENYLDIBORONIC ACID DIPINACOL ESTER;4,4'-BIPHENYLDIBORONIC ACID PINACOL ESTER;4,4'-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BIPHENYL;BIPHENYL-4,4'-DIBORONIC ACID BIS(PINACOL) ESTER;4,4,5,5-tetramethyl-2-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-1,3,2-dioxaborolane;MFCD08669545;SCHEMBL2707320;DTXSID70441269;INNVTCAYPFZCAL-UHFFFAOYSA-N;AKOS016004687;AB45892;AS-2457;CS-W000898;1,3,2-Dioxaborolane, 2,2'-[1,1'-biphenyl]-4,4'-diylbis[4,4,5,5-tetramethyl-;SY051365;B4166;A879444;4,4'-Biphenyldiboronic acid bis(pinacol) ester, 97%;[1,1'-BIPHENYL]-4,4'-DIYLDIBORONIC ACID PINACOL ESTER;4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan2-yl)biphenyl;4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)biphenyl;2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);4,4 inverted exclamation mark -Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl;4,4mu-Biphenyldiboronic acid bis(pinacol) ester;-Biphenyldiboronic acid dipinacol ester;Biphenyl-4,4'-diboronic acid bis(pinacol) ester, 95%;3,2-Dioxaborolane, 2,2'-[1,1'-biphenyl]-4,4'-diylbis[4,4,5,5-tetramethyl- (9CI);4,4'-Biphenyldiboronic acid bis(pinacol) ester;4,4,5,5-tetramethyl-2-[4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl]-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-[4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[4-biphenylyl]-1,3,2-dioxaborolane

Chemical Property of 4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl

Chemical Property:

• Melting Point: 260-262 °C
• Boiling Point: 508.7±43.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 3.95200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 406.2486698
• Heavy Atom Count: 30
• Complexity: 531

Purity/Quality:

98% ^*data from raw suppliers

4,4''-Biphenyldiboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• 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=CC=C(C=C2)C3=CC=C(C=C3)B4OC(C(O4)(C)C)(C)C
• Uses: Biphenyl-4,4'-diboronic acid bis(pinacol) ester is used as pharmaceutical intermediate.

Technology Process of 4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl

There total 22 articles about 4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl 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: 93.0%

4-(4-bromophenyl)bromobenzene (92-86-4) + bis(pinacol)diborane (73183-34-3) → 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl (207611-87-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 10h; Inert atmosphere;

DOI:10.1021/acs.inorgchem.7b03040

Reference yield: 92.0%

4,4'-difluorobiphenyl (398-23-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl (207611-87-8)

Guidance literature:

With 2-((2,4,6-trimethylphenyl)amino)-4-((2,4,6-trimethylphenyl)imino)-2-pentene; magnesium; cobalt(II) chloride; In tetrahydrofuran; at 60 ℃; for 20h; Inert atmosphere; Glovebox;

DOI:10.1021/acs.orglett.8b03167

Reference yield: 89.0%

p-bromophenylboronic acid pinacol ester (68716-49-4) → 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl (207611-87-8)

Guidance literature:

With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; (C₅H₅)2Zr(OC₄H₈)N(Si(CH₃)3)CH(C₆H₅); bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; at 80 ℃; for 16h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.chempr.2021.06.007

upstream raw materials:

p,p'-diaminobiphenyl

bis(pinacol)diborane

Ethyl 4-bromobutyrate

p-bromophenylboronic acid pinacol ester

Downstream raw materials:

N⁴,N^4''-bis(2-(3,4,5-tri-((S)-3',7'-dimethyloctyl)oxybenzamido)ethyl)-[1,1':4',1''-quaterphenyl]-4,4''-dicarboxamide

[8]cyclo-para-phenylene

bacteriopyropheophorbide-a

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran

Refernces

• 1、 Fu, Yue,Liu, Fang-Jie,Liu, Peng,Tang, Jian-Tao,Toste, F. Dean,Wu, Ting-Feng,Ye, Baihua,Zhang, Yue-Jiao. "Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides". supporting information. p. 1963 - 1974. Retrieved 2021/07/07.
• 2、 Sicard, Lambert,Lucas, Fabien,Jeannin, Olivier,Bouit, Pierre-Antoine,Rault-Berthelot, Jo?lle,Quinton, Cassandre,Poriel, Cyril. "[n]-Cyclo-9,9-dibutyl-2,7-fluorene (n=4, 5): Nanoring Size Influence in Carbon-Bridged Cyclo-para-phenylenes". supporting information. p. 11066 - 11072. Retrieved 2020/05/04.