2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(1,3,2-dioxaborolane)

Base Information

• Chemical Name: 2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(1,3,2-dioxaborolane)
• CAS No.: 135615-38-2
• Molecular Formula: C16H16B2O4
• Molecular Weight: 293.923
• DSSTox Substance ID: DTXSID20573640
• Nikkaji Number: J773.468I
• Wikidata: Q82462426
• Mol file: 135615-38-2.mol

Synonyms:135615-38-2;SCHEMBL4262348;DTXSID20573640;4,4'-Di(1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl;2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(1,3,2-dioxaborolane)

Chemical Property of 2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(1,3,2-dioxaborolane)

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 294.1234693
• Heavy Atom Count: 22
• Complexity: 308

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OCCO1)C2=CC=C(C=C2)C3=CC=C(C=C3)B4OCCO4

Technology Process of 2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(1,3,2-dioxaborolane)

There total 3 articles about 2,2'-([1,1'-Biphenyl]-4,4'-diyl)bis(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: 76.0%

triethyl borate (150-46-9) + 4-(4-bromophenyl)bromobenzene (92-86-4) + ethylene glycol (107-21-1) → Biphenyl-4,4'-diboronic acid diethylene glycol ester (135615-38-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; to soln. 4,4'-dibromobiphenyl in THF at -78°C n-BuLi was added, stirred for 1.5 h, B(OEt)3 was added, stirred for 1 h at -78°C andfor 2 h at room temp., concd. in vacuo, dissolved in ethylene glycol - toluene, refluxed for 2 days; react. mixt. was cooled to room temp., glycol layer was extd. with toluene, toluene fraction was concd. in vacuo, recrystn. from CH2Cl2-hexane (1:5), washing with hexane and drying in vacuo;

DOI:10.1021/ic0502731

Reference yield: 65.0%

4-(4-bromophenyl)bromobenzene (92-86-4) + ethylene glycol (107-21-1) → Biphenyl-4,4'-diboronic acid diethylene glycol ester (135615-38-2)

Guidance literature:

4-(4-bromophenyl)bromobenzene; With magnesium; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

ethylene glycol; In toluene; Further stages.; Heating;

DOI:10.1021/jo011073j

Reference yield:

4,4'-biphenyldiboronic acid (4151-80-8) + ethylene glycol (107-21-1) → Biphenyl-4,4'-diboronic acid diethylene glycol ester (135615-38-2)

Guidance literature:

In toluene; for 15h; Heating;

DOI:10.1002/chem.200305245

upstream raw materials:

4-(4-bromophenyl)bromobenzene

ethylene glycol

4,4'-biphenyldiboronic acid

triethyl borate