Biphenyl-3-boronic acid Chemical Properties

Melting point:

193-198 °C (lit.)

Boiling point:

411.0±38.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

solid

pka

8.30±0.10(Predicted)

color 

White to Off-White

Water Solubility 

Insoluble in water.

BRN 

2836311

InChI

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

InChIKey

GOXICVKOZJFRMB-UHFFFAOYSA-N

SMILES

B(C1C=CC=C(C2=CC=CC=C2)C=1)(O)O

CAS DataBase Reference

5122-95-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

Hazard Note 

Corrosive

HS Code 

29163990

MSDS

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

Biphenyl-3-boronic acid Usage And Synthesis

Uses

3-Biphenylboronic Acid is a fluorescent boronic acid useful for sensitive detection of sugars in water.

Chemical Properties

yellow crystal powder

Uses

suzuki reaction

Uses

It is a biological reagent used as a boronate-assisted fluorogenic chemosensor. It is evaluated for pharmacological activity as fatty acid amide hydrolase inhibitors. It is a reactant involved in coupling with potassium cyanate, quinones, or fluorous tagged N-hydroxyphthalimide and direct C-H arylation of electron-deficient heterocycles.

Uses

Biological reagent used as a boronate-assisted fluorogenic chemosensor

Evaluated for pharmacological activity as fatty acid amide hydrolase inhibitors

Reactant involved in:

• Coupling with potassium cyanate, quinones, or fluorous tagged N-hydroxyphthalimide
• Direct C-H arylation of electron-deficient heterocycles

Synthesis

The general procedure for the synthesis of 3-biphenylboronic acid from 3-bromobiphenyl was as follows: 3.8 g (16 mmol) of 3-bromobiphenyl was added to a 300 mL three-neck flask under nitrogen protection. 100 mL of tetrahydrofuran (THF) was added to dissolve, and the solution was subsequently cooled to -80 °C. Under stirring, 11 mL (18 mmol) of n-butyllithium (1.6 mol/L hexane solution) was slowly added dropwise via syringe. After the dropwise addition was completed, the reaction was kept at -80 °C with continued stirring for 1 hour. Subsequently, 2.2 mL (20 mmol) of trimethyl borate was added to the reaction system and the reaction mixture was allowed to gradually warm up to room temperature with continued stirring for 4 hours. Upon completion of the reaction, the reaction was quenched by the addition of about 50 mL of dilute hydrochloric acid (1.0 mol/L) and stirring was continued for 2 hours. The reaction mixture was transferred to a partition funnel and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed sequentially with saturated sodium bicarbonate solution and saturated saline. The organic layer was dried with anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated under reduced pressure to give an oil. Hexane was added to the oily material and a white solid was precipitated. The solid was collected by filtration and dried to give 1.7 g of white powdery 3-biphenylboronic acid in 55% yield.

References

[1] Patent: WO2010/5066, 2010, A1. Location in patent: Page/Page column 178-179
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 21, p. 3813 - 3816
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118

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