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Chemical Structure| 1953-54-4 Chemical Structure| 1953-54-4
Chemical Structure| 1953-54-4

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5-Hydroxyindole is a hydroxylated indole widely found in various pharmacologically active compounds and natural products, reducing ion current desensitization mediated by 5-HT3 receptors in N1E-115 neuroblastoma cells.

Synonyms: NSC 87503

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Product Details of 5-Hydroxyindole

CAS No. :1953-54-4
Formula : C8H7NO
M.W : 133.15
SMILES Code : C1=CC2=C([NH]1)C=CC(=C2)O
Synonyms :
NSC 87503
MDL No. :MFCD00005677
InChI Key :LMIQERWZRIFWNZ-UHFFFAOYSA-N
Pubchem ID :16054

Safety of 5-Hydroxyindole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Hydroxyindole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1953-54-4 ]

[ 1953-54-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1953-54-4 ]
  • [ 54737-34-7 ]
  • [ 619-60-3 ]
  • [ 80792-63-8 ]
  • 2
  • [ 619-60-3 ]
  • [ 80792-63-8 ]
  • [ 1953-54-4 ]
  • [ 54737-34-7 ]
  • 3
  • [ 1953-54-4 ]
  • [ 3107-19-5 ]
  • 5-(2,6-dichloro-4-nitro-phenoxy)-1<i>H</i>-indole [ No CAS ]
  • 4
  • [ 1953-54-4 ]
  • [ 417721-36-9 ]
  • [ 417716-31-5 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine; In ethanol; dimethyl sulfoxide; Example 309 6-Carbamoyl-4-(1H-indol-5-yloxy)-7-methoxyquinoline After mixing 6-carbamoyl-4-chloro-7-methoxyquinoline (2.0 g, 8.4509 mmol), 5-hydroxyindole (1.68 g), diisopropylethylamine (2.2 ml) and N-methylpyrrolidone (2.2 ml), the mixture was heated and stirred at 150° C. for 5 hours. After cooling, the partly solidified reaction mixture was dissolved in dimethylsulfoxide and then adsorbed onto NH silica gel and purified by NH silica gel column chromatography (ethyl acetate-methanol system). The obtained crystals were suspended in ethanol, the suspension was diluted with diethyl ether and hexane, and the crystals were filtered out, washed with diethyl ether:hexane=1:5 and dried by aspiration to obtain the title compound (1.291 g, 3.8698 mmol, 45.79percent) as light yellow crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 4.02 (3H, s), 6.37 (1H, d, J=5.2 Hz), 6.46 (1H, brs), 6.98 (1H, dd, J=2.4 Hz, 8.4 Hz), 7.43-7.45(2H, m), 7.48(1H, s), 7.51(1H, d, J=8.4 Hz), 7.71 (1H, brs), 7.84 (1H, brs), 8.58 (1H, d, J=5.2 Hz), 8.74 (1H, s), 11.29 (1H, s).
  • 5
  • [ 1953-54-4 ]
  • [ 1056934-87-2 ]
  • C20H22N4O3 [ No CAS ]
  • 6
  • [ 1953-54-4 ]
  • [ 7044-92-0 ]
  • 1,4-bis(di(5-hydroxy-1H-indol-3-yl)methyl)-2,5-dimethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With iodine; In acetonitrile; at 20℃; for 0.5h; General procedure: A round-bottomed flask (10 mL) was charged with dialdehyde (1.0 mmol),5-hydroxyindole (0.53 g, 4 mmol), and iodine (0.05 g, 0.2 mmol) in MeCN (5 mL).This mixture was then stirred at room temperature for 0.5 to 8 h. The reactionmixture was treated with aqueous Na2S2O3, andthe solution was extracted with ethyl acetate (3 × 20 mL). The combined organiclayers were dried over MgSO4 and filtered. The solvent wasremoved under reduced pressure, and the residue was subjected to columnchromatography (ethyl acetate/hexane, 1/1), followed by recrystallization
  • 7
  • [ 1953-54-4 ]
  • [ 7072-01-7 ]
  • 1,4-bis(di(5-hydroxy-1H-indol-3-yl)methyl)-2,3,5,6-tetramethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With iodine; In acetonitrile; at 20℃; for 7h; General procedure: A round-bottomed flask (10 mL) was charged with dialdehyde (1.0 mmol),5-hydroxyindole (0.53 g, 4 mmol), and iodine (0.05 g, 0.2 mmol) in MeCN (5 mL).This mixture was then stirred at room temperature for 0.5 to 8 h. The reactionmixture was treated with aqueous Na2S2O3, andthe solution was extracted with ethyl acetate (3 × 20 mL). The combined organiclayers were dried over MgSO4 and filtered. The solvent wasremoved under reduced pressure, and the residue was subjected to columnchromatography (ethyl acetate/hexane, 1/1), followed by recrystallization
 

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