Benzothiophene-3-boronic acid Chemical Properties

Melting point:

225-230 °C(lit.)

Boiling point:

390.2±34.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

8.29±0.30(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C8H7BO2S/c10-9(11)7-5-12-8-4-2-1-3-6(7)8/h1-5,10-11H

InChIKey

QVANIYYVZZLQJP-UHFFFAOYSA-N

SMILES

B(C1=CSC2=CC=CC=C21)(O)O

CAS DataBase Reference

113893-08-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

Benzothiophene-3-boronic acid Usage And Synthesis

Uses

Benzo[b]thien-3-ylboronic acid can be used:

• To prepare thienyl substituted?pyrimidine derivatives as potent antimycobacterial?compounds.
• To prepare 3-O-protected 17-heteroaryl-3-hydroxyestra-1,3,5,16-tetraene-16-carbaldehyde, which in turn is used for the synthesis of heteroarenes-annelated estranes.
• As a substrate in the study of metal-free coupling reactions of allylic alcohols with heteroaryl boronic acids.
• As a starting material for the preparation of thienyl based quinoline and pyridine ligands, which are further used to synthesize platinum complexes.

Synthesis

Under nitrogen protection, 10 g (47 mmol) of 3-bromobenzothiophene was dissolved in 100 ml of tetrahydrofuran (THF) and cooled to -60 °C. 36 ml of hexane solution of n-butyllithium (concentration 1.57 mol/L) was slowly added dropwise, and after the dropwise addition, the reaction mixture was continued to be stirred for 1 hour. Subsequently, 13.3 g (71 mmol) of triisopropyl borate was added and stirring was continued for 1 hour. The reaction system was slowly brought back to room temperature and the reaction was quenched by the addition of 50 ml of saturated aqueous ammonium chloride solution. The reaction mixture was extracted with 100 ml of toluene, the organic phase was washed three times (100 ml each) with distilled water and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was removed by concentration under reduced pressure to afford intermediate B-1. 6.9 g (39 mmol, 83% yield) of the target product, benzothiophene-3-boronic acid, was finally obtained.

References

[1] Patent: EP2617724, 2013, A1. Location in patent: Paragraph 0162; 0163
[2] Patent: EP2628743, 2013, A1. Location in patent: Paragraph 0175

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