4,4'-Biphenyldiboronic acid

Base Information

• Chemical Name: 4,4'-Biphenyldiboronic acid
• CAS No.: 4151-80-8
• Molecular Formula: C12H12B2O4
• Molecular Weight: 241.847
• Hs Code.: 29163990
• European Community (EC) Number: 670-287-0
• UNII: OS4M710QCG
• DSSTox Substance ID: DTXSID40370390
• Nikkaji Number: J1.059.505C
• Wikidata: Q17321243
• Metabolomics Workbench ID: 147200
• ChEMBL ID: CHEMBL109227
• Mol file: 4151-80-8.mol

Synonyms:4,4'-BIPHENYLDIBORONIC ACID;4151-80-8;[1,1'-Biphenyl]-4,4'-diyldiboronic acid;[4-(4-boronophenyl)phenyl]boronic acid;4,4'-Biphenyldiyldiboronic acid;MFCD00151795;OS4M710QCG;BIPHENYL-4,4'-DIYLDIBORONIC ACID;CHEMBL109227;4,4'-Diphenylenebisboronic acid;BIPHENYL-4,4'-DIBORONIC ACID;(4-(4-Boronophenyl)phenyl)boronic acid;(1,1'-Biphenyl)-4,4'-diyldiboronic acid;UNII-OS4M710QCG;4,4'-biphenyldiboric acid;4,4'-Biphenyldiboronicacid;YSWG218;SCHEMBL806835;4,4''-biphenyldiboronic acid;DTXSID40370390;SLHKDOGTVUCXKX-UHFFFAOYSA-N;biphenyl-4,4''-diyldiboronic acid;4,4''-Bis-dihydroxyboranyl-biphenyl;BBL100483;BDBM50067910;STL554277;AKOS005254429;AB03983;CS-W000928;DB02627;GS-5812;PD007808;SY037884;[1,1'-Biphenyl]-4,4'-diyldiboronicacid;AM20040438;B2490;FT-0617001;SR-01000883705;{4-[4-(dihydroxyboranyl)phenyl]phenyl}boronic acid;SR-01000883705-1;4,4 inverted exclamation mark -Biphenyldiboronic Acid;Boronic acid, B,B'-[1,1'-biphenyl]-4,4'-diylbis-;Q17321243;[4'-(dihydroxyboranyl)-[1,1'-biphenyl]-4-yl]boronic acid;415108-00-8

Chemical Property of 4,4'-Biphenyldiboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Melting Point: 300 °C (dec.)
• Boiling Point: 505.9 °C at 760 mmHg
• PKA: 8.25±0.17(Predicted)
• Flash Point: 259.7 °C
• PSA: 80.92000
• Density: 1.31g/cm³
• LogP: -1.28680
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 242.0921692
• Heavy Atom Count: 18
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

4,4'-Biphenyldiboronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnC
• Hazard Codes: Xn,C
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-`37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C2=CC=C(C=C2)B(O)O)(O)O
• Uses: Reactant involved in synthesis of:Organic field-effect transistors based on organic semiconductors containing diazaborolesCycloparaphenylenes via Suzuki coupling1,3,2-Diazaboroine derivatives for organic thin-film transistor applicationsBack-to-back coupled 2,6-bis(triazol-1-yl)pyridine moleculesRectangular host via electrochemical reactions with methylaquacobaloxime and diamineArylboronates from reactions with catechol, dihydroxynaphthalene and diaminobenzenedithiol for use as organic field-effect transistors and light emitting diodes

Technology Process of 4,4'-Biphenyldiboronic acid

There total 7 articles about 4,4'-Biphenyldiboronic acid 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: 82.0%

4,4'-diiodobiphenyl (3001-15-8) → 4,4'-biphenyldiboronic acid (4151-80-8)

Guidance literature:

4,4'-diiodobiphenyl; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; hexane; water;

DOI:10.1021/jo300050m

Reference yield: 64.5%

4-(4-bromophenyl)bromobenzene (92-86-4) → 4,4'-biphenyldiboronic acid (4151-80-8)

Guidance literature:

4-(4-bromophenyl)bromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -30 - 20 ℃; for 1h;

With hydrogenchloride; In water; pH=2;

Reference yield: 48.5%

4,4'-biphenyldiboronic acid bis(neopentyl glycol) cyclic ester (5487-93-4) → 4,4'-biphenyldiboronic acid (4151-80-8)

Guidance literature:

With sodium hydroxide; at 60 ℃; for 1.5h;

DOI:10.1002/anie.201407387

upstream raw materials:

para-diiodobenzene

4-Bromophenylboronic acid

Triisopropyl borate

4-(4-bromophenyl)bromobenzene

Downstream raw materials:

4,4'-biphenyldiboronic acid bis(neopentyl glycol) cyclic ester

C₄₆H₅₂N₁₄

C₆₆H₈₈N₁₀

C₃₈H₂₆N₄

Refernces

• 1、 -. "COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS". Page/Page column 490. . Retrieved 2015/02/02.
• 2、 Basak, Supratim,Hui, Pramiti,Boodida, Sathyanarayana,Chandrasekar, Rajadurai. "Micropatterning of metallopolymers: Syntheses of back-to-back coupled octylated 2,6-Bis(pyrazolyl)pyridine ligands and their solution-processable coordination polymers". experimental part. p. 3620 - 3626. Retrieved 2012/06/15.