benzothiophene-6-carbaldehyde

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benzothiophene-6-carbaldehyde Basic information
Product Name:benzothiophene-6-carbaldehyde
Synonyms:benzothiophene-6-carbaldehyde;Benzo[b]thiophene-6-carboxaldehyde;Benzo[b]thiophene-6-carbaldehyde;1-Benzothiophene-6-carbaldehyde;1-Benzothiophene-6-carboxaldehyde
CAS:6386-80-7
MF:C9H6OS
MW:162.21
EINECS:
Product Categories:
Mol File:6386-80-7.mol
benzothiophene-6-carbaldehyde Structure
benzothiophene-6-carbaldehyde Chemical Properties
Melting point 42.0-42.5 °C
Boiling point 303.2±15.0 °C(Predicted)
density 1.300±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceWhite to yellow Solid
Safety Information
HS Code 2934999090
MSDS Information
benzothiophene-6-carbaldehyde Usage And Synthesis
Synthesis
6-BROMO-BENZO[B]THIOPHENE

17347-32-9

N,N-Dimethylformamide

68-12-2

benzothiophene-6-carbaldehyde

6386-80-7

Magnesium shavings (257 mg, 10.6 mmol) were suspended in anhydrous tetrahydrofuran (THF, 1.7 mL) in a 25 mL three-neck flask and heated to reflux. A solution of 6-bromobenzo[b]thiophene (1.5 g, 7.04 mmol) in anhydrous THF (8.3 mL) was added slowly and dropwise. The reaction mixture was refluxed for 2 h and then cooled to 0°C. Subsequently, N,N-dimethylformamide (1.03 g, 1.09 mL, 14.1 mmol) was slowly added dropwise and the reaction system was allowed to warm up to room temperature naturally. The resulting green suspension was stirred overnight and concentrated. The residue was purified by silica gel column chromatography. The target fraction was collected and dried under vacuum to give benzo[b]thiophene-6-carbaldehyde (821 mg, 72% yield) as a yellow oil.

References[1] Patent: WO2014/86663, 2014, A1. Location in patent: Page/Page column 61
benzothiophene-6-carbaldehyde Preparation Products And Raw materials
Raw materials6-BROMO-BENZO[B]THIOPHENE-->N,N-Dimethylformamide-->Magnesium-->Tetrahydrofuran
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