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CS-W001157 4
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5-Amino-8-hydroxyquinoline

  • CAS No. 13207-66-4

  • Cat. No. CS-W001023
  • Purity≥95%
  • MDL No.MFCD00185837

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

5-Amino-8-hydroxyquinoline|CS-W001023

Structure of 13207-66-4

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General Information

  • CAS No. 13207-66-4
  • Cat. No. CS-W001023
  • Purity ≥95%
  • MDL No. MFCD00185837
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O
  • Molecular Weight 160.18
  • Synonym(s) 5A8HQ; 5AHQ
  • SMILES NC1=C2C=CC=NC2=C(O)C=C1

Description

5-Amino-8-hydroxyquinoline delivers a dual functional handle for coordination chemistry and molecular synthesis. The amino group enables nucleophilic coupling, while the hydroxyquinoline scaffold provides a rigid, electron-rich platform for metal chelation. This compound exhibits enhanced solubility in polar solvents and maintains stability under standard bench conditions, facilitating its use in ligand design and fluorescent probe development.

Application

5-Amino-8-hydroxyquinoline serves as a versatile scaffold in medicinal chemistry and coordination chemistry, enabling efficient metal chelation and serving as a building block for heterocyclic derivatives. Its dual functionality—amine and phenolic hydroxyl groups—facilitates selective derivatization, orthogonally protected transformations, and integration into bioactive molecules. The compound exhibits bench stability and ease of purification, supporting its use in multi-step synthesis and high-throughput screening campaigns.

Synthesis

  • Route1

    References

    • Paige, Mikell; Kosturko, George; Bulut, Guellay; Miessau, Matthew; Rahim, Said; Toretsky, Jeffrey A.; Brown, Milton L.; Ueren, Aykut Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 1 p. 478 - 487
  • Route2

    References

    • Chhajed, Santosh S.; Manisha, Puranik; Bastikar, Virupaksha A.; Animeshchandra, Haldar; Ingle; Upasani, Chandrashekhar D.; Wazalwar, Sachin S. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 12 p. 3640 - 3644
  • Route3
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      63450-86-2
    • ~82%
    • 5-Amino-8-hydroxyquinoline|CS-W001023
      13207-66-4

    References

    • Crosby, Ian T.; Rose, Mark L.; Collis, Maree P.; De Bruyn, Paula J.; Keep, Philip L. C.; Robertson, Alan D. Australian Journal of Chemistry, 2008 , vol. 61, # 10 p. 768 - 784

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

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Computational Chemistry Data

  • TPSA   59.14
  • LogP   1.5226
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   0

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