ChemicalBook--->CAS DataBase List--->3189-13-7

3189-13-7

3189-13-7 Structure

3189-13-7 Structure
IdentificationMore
[Name]

6-Methoxyindole
[CAS]

3189-13-7
[Synonyms]

1H-INDOL-6-YL METHYL ETHER
6-METHOXY-1H-INDOLE
6-METHOXYINDOLE
AKOS JY2082692
METHOXYINDOLE(6-)
1H-Indole, 6-methoxy-
Methoxyindole,96%
5-Methoxyindole,~99%
6-Methoxyindole98%
6-Methoxylindole
6-METHOXYINDOLE 99%
[EINECS(EC#)]

221-689-6
[Molecular Formula]

C9H9NO
[MDL Number]

MFCD00022780
[Molecular Weight]

147.17
[MOL File]

3189-13-7.mol
Questions And AnswerBack Directory
[Synthesis]

Synthesis of 3189-13-7


A method for preparing quinoline and indole derivatives by catalytic oxidation and dehydrogenation of nitrogen-containing heterocyclic compounds using bio-based carbon materials, comprising the following steps:
S1. Using straw as raw material, mixing it with a dehydrating agent (e.g., P2O5, polyphosphoric acid, etc.) at a mass ratio of 1:1 to 1:8, placing it in a hydrothermal reactor with a polytetrafluoroethylene liner, reacting at 150℃-200℃ for 1-8 hours, removing it, washing it with deionized water until neutral, obtaining the catalyst;
S2. Adding 0.5 mmol of 6-methoxy-indoline and 50 mg of catalyst to a reaction tube, using oxygen as the oxidant, Using H2O as solvent, and controlling the temperature at 110℃, the reaction was carried out for 24 hours to obtain the corresponding product, 6-methoxyindole, in 83% yield.

Chemical PropertiesBack Directory
[Appearance]

white shiny crystals
[Melting point ]

90-92 °C (lit.)
[Boiling point ]

105°C 0,2mm
[density ]

1.169±0.06 g/cm3(Predicted)
[Fp ]

105°C/0.2mm
[storage temp. ]

Keep Cold
[solubility ]

Methanol (Slightly)
[form ]

Shiny Crystals
[pka]

17.22±0.30(Predicted)
[color ]

White
[Sensitive ]

Light Sensitive
[BRN ]

116483
[InChI]

InChI=1S/C9H9NO/c1-11-8-3-2-7-4-5-10-9(7)6-8/h2-6,10H,1H3
[InChIKey]

QJRWYBIKLXNYLF-UHFFFAOYSA-N
[SMILES]

N1C2=C(C=CC(OC)=C2)C=C1
[CAS DataBase Reference]

3189-13-7(CAS DataBase Reference)
[NIST Chemistry Reference]

Indole, 6-methoxy-(3189-13-7)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[Hazard Note ]

Irritant/Keep Cold
[HazardClass ]

IRRITANT, LIGHT SENSITIVE
[HS Code ]

29339900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

N,N-Dimethylformamide-->Potassium carbonate-->Palladium-->Acetonitrile-->Dimethyl sulfate-->Glycine-->N,N-Dimethylformamide dimethyl acetal-->Pyrrolidine-->4-Methyl-3-nitrophenol-->2-(5-bromo-4-methoxy-2-nitrophenyl)acetonitrile-->4-Bromo-3-nitroanisole-->4-Methoxyindole-->6-Hydroxyindole-->6-Methoxy-2,3-dihydro-1H-indole-->6-Methoxy-1H-indole-2-carboxylic acid
[Preparation Products]

BANISTERINE MONOHYDRATE-->(S)-2-Amino-3-(6-methoxy-1H-indol-3-yl)-propionic acid-->6-Methoxy-1H-indole-3-carbaldehyde
Hazard InformationBack Directory
[Chemical Properties]

white shiny crystals
[Uses]

6-Methoxyindole was used to study the fluorescence of protonated excited-state forms of serotonin and other related compounds in acid. It was used in the preparation of:
  • tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, potential anticancer immunomodulator
  • indolylindazoles and indolylpyrazolopyridines, interleukin-2 inducible T cell kinase inhibitors
  • diindolyloxyindoles, anticancer agents
  • benzoylpiperazinyl-indolyl ethane dione derivatives, HIV-1 inhibitors
  • 3-aroylindoles as anticancer agents
  • indolyl and isoquinolinyl anthranilates, PPARδ partial agonists
  • heteroaryl ketones, VEGFR-2 inhibitors
[Synthesis Reference(s)]

Synthesis, p. 735, 1986 DOI: 10.1055/s-1986-31759
[Biochem/physiol Actions]

6-Methoxyindole inhibits the chlorinating activity of myeloperoxidase and inhibits the generation of hypochlorous acid released by activated leukocytes.
Spectrum DetailBack Directory
[Spectrum Detail]

6-Methoxyindole(3189-13-7)1HNMR
6-Methoxyindole(3189-13-7)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

6-Methoxyindole, 98%(3189-13-7)
[Alfa Aesar]

6-Methoxyindole, 98+%(3189-13-7)
[Sigma Aldrich]

3189-13-7(sigmaaldrich)
[TCI AMERICA]

6-Methoxyindole,>98.0%(GC)(3189-13-7)
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