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CS-W001157 4
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2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid

  • CAS No. 138731-14-3

  • Cat. No. CS-0074805
  • Purity≥97%
  • MDL No.None

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

2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid|CS-0074805

Structure of 138731-14-3

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General Information

  • CAS No. 138731-14-3
  • Cat. No. CS-0074805
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₁NO₄
  • Molecular Weight 233.22
  • Synonym(s) 2-ETHOXYCABONYL-5-INDOLE CARBOXYLIC ACID
  • SMILES O=C(OCC)C1=CC(C=C2C(O)=O)=C(C=C2)N1

Description

This indole derivative features a carboxylic acid group at the 5-position and an ethoxycarbonyl substituent at the 2-position, enabling direct incorporation into peptide coupling or heterocyclic synthesis. The electron-deficient indole core enhances reactivity in electrophilic substitution, while the ester moiety offers stability under standard conditions.

Application

2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid serves as a versatile building block for indole-based heterocycles, enabling direct functionalization at the C5 position. Its dual carboxylic acid and ester functionalities facilitate sequential transformations, including decarboxylation, amidation, and coupling reactions. The compound exhibits good bench stability and is compatible with standard synthetic protocols, making it well-suited for medicinal chemistry campaigns targeting kinase inhibitors and CNS-active compounds.

Synthesis

  • Route1
    • null|null
      79-37-8
    • In-stock
      Ethyl indole-2-carboxylate|CS-D1745
      3770-50-1
    • ~%
    • In-stock
      2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid|CS-0074805
      138731-14-3

    References

    • Aventis Pharma Deutschland GmbH Patent: EP1479677 A1, 2004 ; Location in patent: Page 51 ; EP 1479677 A1
  • Route2
    • null|null
      301222-77-5
    • ~%
    • In-stock
      2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid|CS-0074805
      138731-14-3

    References

    • Khalaf, Abedawn I.; Pitt, Andrew R.; Suckling, Colin J.; Scobie, Martin; Urwin, John; Waigh, Roger D.; Fishleigh, Robert V.; Young, Stephen C. Journal of Chemical Research, Miniprint, 2000 , # 6 p. 751 - 770
  • Route3
    • 4-Hydrazinylbenzoic acid Lamivudine  Impurity|CS-0229071
      619-67-0
    • ~%
    • In-stock
      2-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid|CS-0074805
      138731-14-3

    References

    • Khalaf, Abedawn I.; Pitt, Andrew R.; Suckling, Colin J.; Scobie, Martin; Urwin, John; Waigh, Roger D.; Fishleigh, Robert V.; Young, Stephen C. Journal of Chemical Research, Miniprint, 2000 , # 6 p. 751 - 770

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   79.39
  • LogP   2.0428
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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