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

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1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one Basic information
Product Name:1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one
Synonyms:1-BENZO[B]THIOPHEN-3-YL-2-BROMOETHAN-1-ONE;1-(1-BENZOTHIOPHEN-3-YL)-2-BROMO-1-ETHANONE;3-(Bromoacetyl)benzo[b]thiophene97%;1-Benzo[b]thiophen-3-yl-2-bromoethan-1-on, 97%;3-(Bromoacetyl)benzo[b]thiophene 97%;1-(Benzo[b]thiophen-3-yl)-2-bromoethan-1-one97%;3-(Bromoacetyl)benzo[b]thiophene;3-(Bromoacetyl)benzothiophene
CAS:26167-45-3
MF:C10H7BrOS
MW:255.13
EINECS:
Product Categories:
Mol File:26167-45-3.mol
1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one Structure
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 Reference26167-45-3
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
MSDS Information
1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one Usage And Synthesis
Chemical PropertiesGray solid
Uses1-(Benzo[b]thiophen-3-yl)-2-bromoethanone is one of the thiazole analogs of indomethacin as selective COX-2 inhibitors.
Synthesis
3-Acetyl benz[b]thiophene

1128-05-8

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

26167-45-3

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 Preparation Products And Raw materials
Raw materialsDichloromethane-->Bromine-->Carbon tetrachloride-->Acetyl chloride-->Thianaphthene-->Tin tetrachloride-->3-Acetyl benz[b]thiophene-->Ethyl acetate-->Cupric bromide-->Chloroform
Tag:1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one(26167-45-3) Related Product Information
2-Bromoacetophenone Benzo[b]thien-2-ylboronic acid Tetrahydrothiophen-3-one 3'-Bromoacetophenone 4'-Bromoacetophenone Dibenzothiophene 3-Acetyl benz[b]thiophene 1-(1-Benzothiophen-5-yl)-2-bromo-1-ethanone 1-(1-Benzothiophen-2-yl)-2-bromo-1-ethanone 2-Bromo-1-(3-thienyl)-1-ethanone 1-Benzothiophene-3-carbaldehyde AKOS 93688 2-Bromo-1-(5-bromo-3-benzo[b]thienyl)ethanone AKOS 92964 1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one