4-Biphenylboronic acid

Base Information

• Chemical Name: 4-Biphenylboronic acid
• CAS No.: 5122-94-1
• Molecular Formula: C12H11BO2
• Molecular Weight: 198.029
• Hs Code.: 29310095
• Mol file: 5122-94-1.mol

Synonyms:4-Biphenylboronicacid (6CI,7CI,8CI);Boronic acid, [1,1'-biphenyl]-4-yl- (9CI);(1,1'-Biphenyl)-4-boronic acid;4-(Dihydroxyboryl)-1,1'-biphenyl;4-Phenylbenzeneboronic acid;p-Biphenylboronic acid;

Chemical Property of 4-Biphenylboronic acid

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 232-245 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 385.504 °C at 760 mmHg
• PKA: 8.61±0.10(Predicted)
• Flash Point: 186.946 °C
• PSA: 40.46000
• Density: 1.184 g/cm³
• LogP: 1.03340
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Acetone,Methanol
• Water Solubility.: Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

4-Biphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: suzuki reaction: Suzuki coupling of 2-(4-bromophenyl)thiophene with phenylboronic acid and 4-biphenylboronic acid are used for the preparation of 4-(2-thieny)biphenyl and 4-(2-thienyl)-1,1':4,1''-biphenyl respectively. Coupling of two equivalents of 4-(2-thienyl)phenylboronic acid with 1,4-diiodobenzene gives 4,4''-bis(2-thienyl)-1,1':4,1''-terphenyl and with 2,5-diiodothiophene, 2,5-bis[4-(2-thienyl)-phenyl]-thiophene is obtained. Used in Suzuki reactions and as intermediates of liquid crystals.

Technology Process of 4-Biphenylboronic acid

There total 24 articles about 4-Biphenylboronic 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: 95.0%

4-bromophenylboronic acid MIDA ester + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; In tetrahydrofuran; at 90 ℃; for 4h; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1021/acs.orglett.5b03030

Reference yield: 86.0%

C18H14B2Br2O6(2-)*2K(1+) + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

Guidance literature:

With potassium carbonate; In ethanol; water; at 50 ℃; for 5h; Inert atmosphere;

Reference yield: 86.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

Guidance literature:

4-bromo-1,1'-biphenyl; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2.5h;

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

With hydrogenchloride; In tetrahydrofuran; hexane; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jp010869j

upstream raw materials:

boric acid tributyl ester

4-biphenylylmagnesium bromide

4-bromo-1,1'-biphenyl

4-iodo-biphenyl

Downstream raw materials:

[1,1';4',1'']terphenyl

5,5'-di([1,1'-biphenyl]-4-yl)-2,2'-bithiophene

8-biphenyl-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

7-Biphenyl-4-yl-benzo[1,2,4]triazin-3-ylamine

Refernces

• 1、 Bakir, Mohammed,Bohari Yamin, M.,Lawrence, Mark W.. "Novel κ2-Nim,S- and κ4-C,Nim,(μ-S),(μ-S)-coordination of di-2-thienyl ketone thiosemicarbazone (dtktsc). Hydrogen evolution and catalytic properties of palladacyclic [Pd(κ4-C,Nim,(μ-S),(μ-S)-dtktsc-2H)]4". . . Retrieved 2020.
• 2、 Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū. "Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems". supporting information. p. 353 - 359. Retrieved 2019/12/15.