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CS-W001157 4
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4,5,6,7-Tetrahydro-1h-indole-2-carboxylic acid

  • CAS No. 131172-64-0

  • Cat. No. CS-0217389
  • Purity≥98%
  • MDL No.None

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

4,5,6,7-Tetrahydro-1h-indole-2-carboxylic acid|CS-0217389

Structure of 131172-64-0

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General Information

  • CAS No. 131172-64-0
  • Cat. No. CS-0217389
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁NO₂
  • Molecular Weight 165.19
  • Synonym(s) 1H-Indole-2-carboxylicacid,4,5,6,7-tetrahydro-(9CI)
  • SMILES C1CCC2=C(C1)C=C(C(=O)O)N2

Description

4,5,6,7-Tetrahydro-1H-indole-2-carboxylic acid features a saturated indoline core with a carboxylic acid group at the 2-position, offering enhanced solubility and stability compared to aromatic analogs. This scaffold integrates readily into bioactive molecule design, particularly in CNS-targeted compounds and kinase inhibitors. The acidic proton enables salt formation and conjugation, while the hydrophobic indoline ring supports membrane permeability.

Application

4,5,6,7-Tetrahydro-1H-indole-2-carboxylic acid serves as a versatile scaffold in medicinal chemistry, enabling the construction of biologically relevant heterocycles. Its carboxylic acid functionality facilitates amide coupling and esterification, while the saturated indoline core offers enhanced metabolic stability. The compound exhibits good bench stability and is compatible with standard purification methods, making it a practical building block for API development and combinatorial synthesis workflows.

Synthesis

  • Route1

    References

    • Varnavas, Antonio; Lassiani, Lucia; Valenta, Valentina; Berti, Federico; Tontini, Andrea; Mennuni, Laura; Makovec, Francesco European Journal of Medicinal Chemistry, 2004 , vol. 39, # 1 p. 85 - 97
  • Route2

    References

    • Clarisse, Damien; Fenet, Bernard; Fache, Fabienne Organic and Biomolecular Chemistry, 2012 , vol. 10, # 32 p. 6587 - 6594
  • Route3
    • 2,2,2-Trifluoro-1-(4,5,6,7-tetrahydro-1h-indol-2-yl)ethan-1-one|CS-0304134
      131172-58-2
    • ~86%
    • In-stock
      4,5,6,7-Tetrahydro-1h-indole-2-carboxylic acid|CS-0217389
      131172-64-0

    References

    • Sobenina, L. N.; Sergeeva, M. P.; Mikhaleva, A. I.; Sigalov, M. V.; Korostova, S. E.; et al. Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990 , vol. 26, # 5 p. 516 - 520 Khimiya Geterotsiklicheskikh Soedinenii, 1990 , # 5 p. 612 - 616

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

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Computational Chemistry Data

  • TPSA   53.09
  • LogP   1.5917
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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