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2-Bromo-5-benzoylthiophene

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2-Bromo-5-benzoylthiophene Basic information
Product Name:2-Bromo-5-benzoylthiophene
Synonyms:(5-BROMOTHIEN-2-YL)(PHENYL)METHANONE;2-BENZOYL-5-BROMOTHIOPHENE;2-BROMO-5-BENZOYLTHIOPHENE 98.0%MIN;2-Bromo-5-benzoylthiophene ,98%;2-BROMO-5-BENZOYLTHI;2-Bromo-5-bezoylthiophene;(5-Bromothiophen-2-yl)(phenyl)methanone;Methanone, (5-bromo-2-thienyl)phenyl-
CAS:31161-46-3
MF:C11H7BrOS
MW:267.14
EINECS:608-584-4
Product Categories:Heterocycle-oher series
Mol File:31161-46-3.mol
2-Bromo-5-benzoylthiophene Structure
2-Bromo-5-benzoylthiophene Chemical Properties
Melting point 45-46 °C
Boiling point 361.7±27.0 °C(Predicted)
density 1.542±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
form powder to crystal
color White to Yellow to Green
CAS DataBase Reference31161-46-3(CAS DataBase Reference)
Safety Information
Risk Statements 20/21/22-36/37/38
Safety Statements 22-26-36/37/39
HS Code 29309090
MSDS Information
2-Bromo-5-benzoylthiophene Usage And Synthesis
Chemical PropertiesYellow to brown powder
Synthesis
2-Bromothiophene

1003-09-4

Benzoyl chloride

98-88-4

2-BROMO-5-BENZOYLTHIOPHENE

31161-46-3

Aluminum chloride (5.34 g, 40.0 mmol) was added batchwise to a solution of carbon disulfide (120 mL) containing benzoyl chloride (2.81 g, 20.0 mmol) and 2-bromothiophene (3.42 g, 21.0 mmol) over a period of 10 minutes under vigorous stirring. The reaction mixture was continued to be magnetically stirred for 2.5 hours at room temperature. Upon completion of the reaction, the reaction was quenched with 100 mL of aqueous 1 M hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with carbon disulfide (3 x 50 mL). The organic phases were combined and washed with water (3 x 100 mL) and subsequently dried with anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ether=9:1) to give 5.14 g (96% yield) of a yellow crystalline product with a melting point of 41-43°C. The product was purified by 1H NMR (1H NMR) with a melting point of 1H NMR (1H NMR). The product was characterized by 1H NMR (CDCl3): δ 7.84 (d, 2H, 3J=8.0 Hz), 7.62 (t, 1H, 3J=7.2 Hz), 7.52 (t, 2H, 3J=7.5 Hz), 7.40 (d, 2H, 3J=3.5 Hz), 7.15 (d, 2H, 3J=4.0 Hz).

References[1] Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13476 - 13477
[2] Patent: WO2007/50049, 2007, A1. Location in patent: Page/Page column 27-29
[3] Patent: US5650522, 1997, A
[4] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 5,29
[5] Journal of the American Chemical Society, 1953, vol. 75, p. 1115
2-Bromo-5-benzoylthiophene Preparation Products And Raw materials
Raw materials2-Bromothiophene-->Benzoyl chloride-->Aluminum chloride-->Carbon disulfide
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