Benzo[b]thien-2-ylboronic acid Chemical Properties

Melting point:

254-256 °C

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

solubility 

soluble in Tetrahydrofuran

form 

Powder

pka

6.99±0.30(Predicted)

color 

White to off-white

Water Solubility 

Insoluble in water.

BRN 

1637924

InChI

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

InChIKey

YNCYPMUJDDXIRH-UHFFFAOYSA-N

SMILES

B(C1SC2=CC=CC=C2C=1)(O)O

CAS DataBase Reference

98437-23-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

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

Benzo[b]thien-2-ylboronic acid Usage And Synthesis

Uses

Thianaphthene-2-boronic Acid is used in the preparation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.

Chemical Properties

white tooff-whitepowder

Uses

suzuki reaction

Uses

Thianaphthene-2-boronic Acid is used in the preparation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.

Uses

Reactant involved in:

• PDE4 inhibitors
• Chemoselective modification of oncolytic adenovirus
• Synthesis of phosphorescent sensor for quantification of copper(II) ion
• UV promoted phenanthridine syntheses
• Preparation of CYP11B1 inhibitors for treatment of cortisol dependent diseases
• Suzuki-Miyaura cross-coupling reactions

Synthesis

The general procedure for the synthesis of benzothiophene-2-boronic acid from trimethyl borate and benzothiophene was as follows: 144 g (554 mmol) of benzothiophene and 1,000 mL of tetrahydrofuran were added to a 2L reactor and mixed with stirring. After cooling the reaction mixture to -78 °C, 415 mL of n-butyllithium (1.6 M hexane solution) was slowly added dropwise and stirred for 1 hour at this temperature. Subsequently, the temperature of the reaction mixture was gradually brought to room temperature and kept stirring for 12 hours. After cooling again to -78 °C, 80.3 mL (664 mmol) of trimethyl borate was slowly added dropwise and stirred at room temperature for 2 hours. After completion of the reaction, the mixture was cooled to 0°C and acidified by adding 2N aqueous hydrochloric acid. Extraction was separated with ethyl acetate and distilled water and the organic layer was collected. The organic layer was concentrated under reduced pressure and filtered to give 86 g of the intermediate benzothiophene-2-boronic acid in 87.3% yield.

References

[1] Patent: KR2016/2328, 2016, A. Location in patent: Paragraph 0413-0415

Benzo[b]thien-2-ylboronic acid(98437-23-1)Related Product Information

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• Benzo[b]thien-2-ylboronic acid