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CS-W001157 4
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1,2,3,4-Tetrahydroquinoline-6-carboxylic acid

  • CAS No. 5382-49-0

  • Cat. No. CS-W006431
  • Purity≥95%
  • MDL No.MFCD00957087

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

1,2,3,4-Tetrahydroquinoline-6-carboxylic acid|CS-W006431

Structure of 5382-49-0

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General Information

  • CAS No. 5382-49-0
  • Cat. No. CS-W006431
  • Purity ≥95%
  • MDL No. MFCD00957087
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₁NO₂
  • Molecular Weight 177.20
  • Synonym(s) Tetrahydroquinoline-6-carboxylic acid
  • SMILES O=C(C1=CC2=C(NCCC2)C=C1)O

Description

1,2,3,4-Tetrahydroquinoline-6-carboxylic acid features a fully saturated quinoline core with a carboxylic acid group at the C6 position, enabling direct conjugation or derivatization. This scaffold combines enhanced solubility and metabolic stability with a rigid, electron-rich aromatic system, making it valuable for medicinal chemistry applications. The pendant carboxylic acid serves as a versatile handle for peptide coupling, esterification, or amide formation under standard conditions.

Application

1,2,3,4-Tetrahydroquinoline-6-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry and natural product synthesis. Its carboxylic acid functionality enables direct derivatization via amide, ester, or acyl chloride formation, while the saturated quinoline core offers enhanced metabolic stability and tunable lipophilicity. The molecule exhibits good bench stability and compatibility with standard coupling protocols, facilitating integration into multi-step synthetic sequences targeting bioactive scaffolds.

Synthesis

  • Route1

    References

    • Zhang, Cunyu; Westaway, Susan M.; Speake, Jason D.; Bishop, Michael J.; Goetz, Aaron S.; Carballo, Luz Helena; Hu, Mike; Epperly, Andrea H. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 2 p. 670 - 676
  • Route2
    • 1-Acetyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile|CS-0456222
      851202-94-3
    • ~61%
    • In-stock
      1,2,3,4-Tetrahydroquinoline-6-carboxylic acid|CS-W006431
      5382-49-0

    References

    • H. LUNDBECK A/S Patent: WO2005/39572 A1, 2005 ; Location in patent: Page/Page column 31-32 ;
  • Route3

    References

    • Marchand, Pascal; Puget, Alain; Le Baut, Guillaume; Emig, Peter; Czech, Michael; Guenther, Eckhard Tetrahedron, 2005 , vol. 61, # 16 p. 4035 - 4041

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   49.33
  • LogP   1.7429
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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