1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one Chemical Properties

Melting point:

138 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

crystalline solid

color 

White

CAS DataBase Reference

26167-45-3

Safety Information

Hazard Codes 

C

Risk Statements 

36/37/38-34

Safety Statements 

26-36/37/39-45-26/37/39

RIDADR 

3261

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HS Code 

29349990

1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one Usage And Synthesis

Chemical Properties

Gray solid

Uses

1-(Benzo[b]thiophen-3-yl)-2-bromoethanone is one of the thiazole analogs of indomethacin as selective COX-2 inhibitors.

Synthesis

General procedure for the synthesis of 1-benzo[b]thiophen-3-yl-2-bromoethyl-1-one from 1-(benzo[b]thiophen-3-yl)ethanone: 1-(benzo[b]thiophen-3-yl)ethanone (21 mmol) was dissolved in a mixed solvent of ethyl acetate (50 ml) and chloroform (50 ml), followed by addition of copper(II) bromide (40.2 mmol). The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the resulting copper bromide precipitate was removed by filtration. The filtrate was washed sequentially with distilled water (20 ml x 3) to remove water-soluble impurities and then dried with anhydrous sodium sulfate overnight. After drying, the desiccant was removed by filtration and the residue was washed with a small amount of ethyl acetate. The solvent in the filtrate was evaporated by rotary evaporator to obtain the crude product. Finally, the crude product was purified by ethanol recrystallization to give a light yellow crystalline solid in about 75% yield.

References

[1] Patent: EP2311828, 2011, A1. Location in patent: Page/Page column 9
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 16, p. 1959 - 1964
[3] Patent: WO2014/31784, 2014, A1. Location in patent: Paragraph 0548
[4] Journal of Chemical Research, Miniprint, 1994, # 5, p. 1042 - 1059
[5] Journal of Scientific and Industrial Research, 1955, vol. 14 B, p. 11

1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one(26167-45-3)Related Product Information

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