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5-Bromo-3-cyanoindole

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CAS:90271-86-6
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  • 5-Bromo-3-cyanoindole
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  • CAS:90271-86-6
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  • 5-Bromo-3-cyanoindole
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  • 5-Bromo-3-cyanoindole
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  • 2019-12-25
  • CAS:90271-86-6
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5-Bromo-3-cyanoindole Basic information
Product Name:5-Bromo-3-cyanoindole
Synonyms:5-BROMO-3-CYANOINDOLE;5-BROMO-3-FLUOROINDOLE;5-Bromo-1H-indole-3-carbonitrile;5-BroMoindole-3-lindoleforMonitrile;1H-Indole-3-carbonitrile, 5-bromo-;5-Bromo-3-cyano-1H-indole;5-Bromo-1H-indole-3-carbonitrile 97%;5-Bromoindole-3-carbonitrile
CAS:90271-86-6
MF:C9H5BrN2
MW:221.05
EINECS:
Product Categories:pharmacetical;Indole;Organohalides
Mol File:90271-86-6.mol
5-Bromo-3-cyanoindole Structure
5-Bromo-3-cyanoindole Chemical Properties
Boiling point 405.9±25.0 °C(Predicted)
density 1.74±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka13+-.0.30(Predicted)
AppearanceLight brown to brown Solid
InChIInChI=1S/C9H5BrN2/c10-7-1-2-9-8(3-7)6(4-11)5-12-9/h1-3,5,12H
InChIKeyZPUQCVKBNRGSAP-UHFFFAOYSA-N
SMILESN1C2=C(C=C(Br)C=C2)C(C#N)=C1
Safety Information
HS Code 2933998090
MSDS Information
5-Bromo-3-cyanoindole Usage And Synthesis
Synthesis
5-Bromoindole

10075-50-0

Chlorosulfonyl isocyanate

1189-71-5

5-Bromo-3-cyanoindole

90271-86-6

GENERAL METHOD: To a solution of 5-bromoindole (6.8 mmol) in anhydrous acetonitrile (6.0 mL) was slowly added chlorosulfonyl isocyanate (CSI) (0.63 mL, 7.25 mmol) dropwise at 0 °C, and the reaction mixture was kept stirring at 0 °C for 2 hours. Subsequently, anhydrous dimethylformamide (DMF) (1.3 mL, 170.0 mmol) was added dropwise and stirring was continued at 0 °C for 2 hours. Upon completion of the reaction, the mixture was poured into water and the resulting precipitate was collected by filtration. The precipitate was dried over anhydrous Na2SO4 and purified by column chromatography with the eluent being petroleum ether/ethyl acetate (40/60) or pure ethyl acetate to afford the target product 5-bromo-3-cyanoindole.

References[1] Marine Drugs, 2018, vol. 16, # 8,
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