4-Biphenylboronic acid Chemical Properties

Melting point:

232-245 °C (lit.)

Boiling point:

385.5±35.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Acetone,Methanol

pka

8.61±0.10(Predicted)

form 

Powder

color 

White

Water Solubility 

Insoluble in water.

BRN 

2937410

InChI

InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H

InChIKey

XPEIJWZLPWNNOK-UHFFFAOYSA-N

SMILES

B(C1=CC=C(C2=CC=CC=C2)C=C1)(O)O

CAS DataBase Reference

5122-94-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36-24/25

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29310095

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Biphenylboronic acid Usage And Synthesis

Chemical Properties

Solid

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.

Uses

Used in Suzuki reactions and as intermediates of liquid crystals.

Synthesis

The general procedure for the synthesis of 4-biphenylboronic acid from 4-bromobiphenyl was as follows: 4-bromobiphenyl (30 g, 0.12 mol) was added to a single-neck flask and the reaction was carried out under argon protection. Tetrahydrofuran (THF) (500 mL) was added and stirred at -78 °C for 10 min. Slowly n-butyllithium (2.5 M in hexane) (77 mL, 0.19 mol) was added and the mixture was stirred at -78 °C for 1 hour. Subsequently, dimethyl borate (21.9 mL, 0.19 mol) was added at -78 °C and stirring was continued at -78 °C for 30 min, then brought to room temperature and stirred for 4 hours. After completion of the reaction, extraction was carried out with distilled water and ethyl acetate (EA) and the organic layer was dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed using a rotary evaporator. Finally, pure 4-biphenylboronic acid (21 g, 84% yield) was isolated by column chromatography using hexane and ethyl acetate (EA) as eluents.

References

[1] Patent: WO2011/105700, 2011, A1. Location in patent: Page/Page column 18; 19; 21; 22
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1404 - 1408
[3] Tetrahedron, 2007, vol. 63, # 20, p. 4297 - 4303
[4] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1013 - 1030
[5] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571

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