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Methyl 5-methoxy-1H-indole-2-carboxylate

  • CAS No. 67929-86-6

  • Cat. No. CS-0102186
  • Purity≥98%
  • MDL No.MFCD01074509

*For research and further manufacturing use only, not for direct human use.

Methyl 5-methoxy-1H-indole-2-carboxylate|CS-0102186

Structure of 67929-86-6

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General Information

  • CAS No. 67929-86-6
  • Cat. No. CS-0102186
  • Purity ≥98%
  • MDL No. MFCD01074509
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₁NO₃
  • Molecular Weight 205.21
  • Synonym(s) METHYL 5-METHOXYINDOLE-2-CARBOXYLATE
  • SMILES O=C(C(N1)=CC2=C1C=CC(OC)=C2)OC

Description

Methyl 5-methoxy-1H-indole-2-carboxylate features a benzene-fused pyrrole core with a methoxy group at the 5-position and a methyl ester at C2. This electron-rich indole derivative exhibits enhanced solubility in organic solvents and stability under standard bench conditions, enabling straightforward incorporation into synthetic sequences for pharmaceutical intermediates and functional materials.

Application

Methyl 5-methoxy-1H-indole-2-carboxylate serves as a versatile building block for indole-based scaffolds, enabling efficient access to functionalized heterocycles via standard coupling and oxidation protocols. The methoxy group at the 5-position enhances solubility and modulates electronic properties, while the ester functionality facilitates downstream transformations including hydrolysis, reduction, or nucleophilic displacement. Bench-stable and readily purified by column chromatography, it functions effectively in both medicinal chemistry and process-scale synthesis.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      5-Methoxy-1H-indole-2-carboxylic acid|CS-W010727
      4382-54-1
    • ~96%
    • In-stock
      Methyl 5-methoxy-1H-indole-2-carboxylate|CS-0102186
      67929-86-6

    References

    • WO2012/59776 A1, ; Page/Page column 57 ; WO 2012/059776 A1
  • Route2
    • null|null
      75525-73-4
    • ~%
    • In-stock
      Methyl 5-methoxy-1H-indole-2-carboxylate|CS-0102186
      67929-86-6

    References

    • US4851417 A1, ;
  • Route3
    • null|null
      651331-47-4
    • ~93%
    • In-stock
      Methyl 5-methoxy-1H-indole-2-carboxylate|CS-0102186
      67929-86-6

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 6 p. 1740 - 1742

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   51.32
  • LogP   1.9631
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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