1,4-Phenylenebisboronic acid Chemical Properties

Melting point:

>350 °C(lit.)

Boiling point:

420.1±55.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.30±0.17(Predicted)

form 

liquid

color 

white to off-white

Water Solubility 

Soluble in water 2.5%.

BRN 

2836921

InChI

InChI=1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H

InChIKey

BODYVHJTUHHINQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4612-26-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,C,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

36-26

WGK Germany 

3

Hazard Note 

Corrosive

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29310095

MSDS

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

1,4-Phenylenebisboronic acid Usage And Synthesis

Chemical Properties

1,4-Phenylenebisboronic acid is off-white powder

Uses

Reagent used for . Externally initiated Kumada catalyst-transfer polycondensation . Suzuki-Miyaura cross-coupling reactions . Energy transfer processes in optoelectronic devices . Palladium-catalyzed sequential alkenylation and conjugate addition reactions . Scholl cyclizations

Uses

suzuki reaction

Uses

It is used for palladium-catalyzed sequential alkenylation and conjugate addition reactions, scholl cyclizations, Suzuki-Miyaura cross-coupling reactions. It is also used in the preparation of indolizine derivatives as OLEDs, in organic thin-film transistors, Fluorescence and solution-processable coordination polymers.

Synthesis

Under the protection of nitrogen atmosphere, 200 mL of tetrahydrofuran (THF) was added to the reaction flask and cooled to 15°C. 0 g (0.62 mmol) of magnesium and 1.0 g (0.004 mol) of iodine were slowly added followed by the dropwise addition of 300 mL of THF solution containing 68.4 g (0.29 mol) of 1,4-dibromobenzene at a controlled titration rate maintaining the reaction temperature at 30°C. The reaction was continued for 3 hours. After completion, the reaction was continued for 3 hours. After completion of the reaction, the reaction mixture was cooled to -70°C and a mixed solution consisting of trimethyl borate (78.5 mL, 0.72 mol) and 300 mL of THF was slowly added dropwise. After the dropwise addition was completed, the reaction was continued at -70°C for 1 hour, then slowly warmed to room temperature and stirred for 12 hours. To the reaction mixture was added 950 mL of 2.5 M hydrochloric acid, stirred rapidly for 15 minutes and the solid product was collected by filtration. The solid was washed 3 times with 300 mL of hexane and finally dried under vacuum to give 40.7 g of white solid 1,4-phenylenediboronic acid in 84.6% yield.

References

[1] Patent: CN103570530, 2016, B. Location in patent: Paragraph 0042; 0043

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