3-Hydroxyphenylboronic acid Chemical Properties

Melting point:

210-213 °C (dec.) (lit.)

Boiling point:

370.0±44.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder, Crystals and/or Chunks

pka

pK1:8.55;pK2:10.84 (25°C)

color 

Pink to gray to tan

BRN 

3240771

InChI

InChI=1S/C6H7BO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8-10H

InChIKey

WFWQWTPAPNEOFE-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(O)=C1)(O)O

CAS DataBase Reference

87199-18-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

3-Hydroxyphenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

suzuki reaction

Uses

3-Hydroxyphenylboronic acid (3-HPBA) can be used as a reagent:

• In Suzuki-Miyaura coupling reactions with aryl halides for the formation of C-C bond in the presence of Pd catalyst.
• ?To synthesize boron/nitrogen-doped polymer nano/microspheres by hydrothermal polymerization with formaldehyde and ammonia.??????
• To prepare carbon quantum dots based on 3-HPBA as selective fructose sensor.?????
• In the development of modified electrodes for electrochemical biosensors.

Synthesis

(vi) Preparation of 3-hydroxyphenylboronic acid: m-Bromophenol (8.65 g, 50 mmol) was dissolved in anhydrous tetrahydrofuran (150 mL) and sodium hydride (60%, 2.4 g, 60 mmol) was added at room temperature. After 1 hour of reaction, sec-butyl lithium (1.3 M, 50 mL, 65 mmol) was added slowly and dropwise to the reaction solution at -78 °C. Stirring was continued at this temperature for 30 min, followed by the addition of trimethyl borate (15 mL). The reaction system was gradually warmed to room temperature and maintained for 2 hours. Upon completion of the reaction, the reaction was quenched with deionized water (50 mL) and extracted with dichloromethane (2 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to afford 3-hydroxyphenylboronic acid as a white solid (4.0 g, 58% yield), and the product was used directly in the subsequent Suzuki coupling reaction without further purification.

References

[1] Patent: US2003/187022, 2003, A1

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