6-BROMO-BENZO[B]THIOPHENE Chemical Properties

Melting point:

56.0 to 60.0 °C

Boiling point:

140°C/30mmHg(lit.)

Density 

1.649±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C8H5BrS/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5H

InChIKey

OQIMJOXSDVGEBU-UHFFFAOYSA-N

SMILES

C12=CC(Br)=CC=C1C=CS2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

HS Code 

2934999090

6-BROMO-BENZO[B]THIOPHENE Usage And Synthesis

Chemical Properties

off-white powder

Uses

6-Bromobenzo[b]thiophene is a reagent for the synthesis of aminobenzo[b]thiophene 1,1-dioxides as STAT3 inhibitors with antitumor activities being an attractive therapeutic target for cancer therapy.

Synthesis

Part C. Preparation of 6-bromobenzo[b]thiophene. 6-Bromobenzo[b]thiophene-2-carboxylic acid (0.70 g, 2.73 mmol) from Part B was mixed with DBU (1.35 mL, 8.94 mmol) in DMA (6 mL) in a sealed tube and heated in a microwave reactor for 70 min at 200 °C. After completion of the reaction, the resulting dark solution was diluted with 1 M HCl (20 mL) and extracted with dichloromethane (2 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane as eluent to afford 6-bromobenzo[b]thiophene as an oil (0.484 g, 83% yield).

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 264 - 281
[2] Tetrahedron Letters, 2004, vol. 45, # 52, p. 9645 - 9647
[3] Patent: WO2009/39134, 2009, A1. Location in patent: Page/Page column 159
[4] Patent: WO2012/149413, 2012, A1. Location in patent: Page/Page column 59
[5] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 538 - 550

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