4-Dibenzothiopheneboronic acid Chemical Properties

Melting point:

327-330 °C (lit.)

Boiling point:

480.2±37.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Powder

pka

8.29±0.30(Predicted)

color 

White

BRN 

197863

InChI

InChI=1S/C12H9BO2S/c14-13(15)10-6-3-5-9-8-4-1-2-7-11(8)16-12(9)10/h1-7,14-15H

InChIKey

GOXNHPQCCUVWRO-UHFFFAOYSA-N

SMILES

B(C1=C2SC3=CC=CC=C3C2=CC=C1)(O)O

CAS DataBase Reference

108847-20-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

4-Dibenzothiopheneboronic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of dibenzothiophene-4-boronic acid from 4-bromodibenzothiophene and trimethyl borate was as follows: first, 4-bromodibenzothiophene was dissolved in anhydrous tetrahydrofuran (THF), and the reaction system was cooled to -78 °C. Under nitrogen protection, n-butyllithium (2.5 M hexane solution) was slowly added dropwise, maintaining the reaction temperature at -78 °C. After the dropwise addition, the reaction system was warmed to 0 °C and stirring was continued for 1 hour. Subsequently, the reaction system was again cooled to -78 °C and trimethyl borate was slowly added dropwise. After completion of dropwise addition, the reaction system was gradually warmed to room temperature and stirred for 12 hours. After completion of the reaction, the reaction mixture was slowly poured into 2N aqueous hydrochloric acid solution and stirred for 30 minutes. The aqueous phase was extracted with ether and the organic phase was combined. The organic phase was dried with anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford the target product dibenzothiophene-4-boronic acid in 82% yield.

References

[1] Patent: KR101497123, 2015, B1. Location in patent: Paragraph 0088; 0089; 0090; 0091; 0092
[2] RSC Advances, 2015, vol. 5, # 88, p. 72009 - 72018
[3] Journal of Fluorescence, 2017, vol. 27, # 2, p. 451 - 461

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