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CS-W001157 4
Total: USD 88.00

3-Nitroquinolin-4-ol

  • CAS No. 50332-66-6

  • Cat. No. CS-M2023
  • Purity≥97%
  • MDL No.MFCD00277722

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

3-Nitroquinolin-4-ol|CS-M2023

Structure of 50332-66-6

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General Information

  • CAS No. 50332-66-6
  • Cat. No. CS-M2023
  • Purity ≥97%
  • MDL No. MFCD00277722
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆N₂O₃
  • Molecular Weight None
  • Synonym(s) 3-Nitro-4-hydroxyquinoline; 3-Nitro-4-quinolinol; 4-Hydroxy-3-nitroquinoline
  • SMILES OC1=C([N+]([O-])=O)C=NC2=CC=CC=C12

Description

3-Nitroquinolin-4-ol features a quinoline core bearing a nitro group at the 3-position and a hydroxyl at the 4-position, creating a rigid, electron-deficient scaffold. This arrangement enables direct participation in transition-metal-catalyzed cross-couplings and facilitates hydrogen bonding in supramolecular architectures. The compound exhibits bench-stable handling under standard conditions.

Application

3-Nitroquinolin-4-ol serves as a versatile building block in medicinal chemistry, enabling direct access to quinoline-based pharmacophores. Its dual functionality—nitro group at C3 and hydroxyl at C4—facilitates selective transformations, including reduction, coupling, and cyclization reactions. The compound exhibits good bench stability and compatibility with common protecting group strategies, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • Minnesota Mining and Manufacturing Company Patent: US5175296 A1, 1992 ;
  • Route2
    • 2-(2-Nitroethylidene)aminobenzoic acid|CS-M2022
      121845-92-9
    • ~49%
    • In-stock
      3-Nitroquinolin-4-ol|CS-M2023
      50332-66-6

    References

    • THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPT. OF HEALTH AND HUMAN SERVICES; UNIVERSITEIT LEIDEN Patent: WO2007/89507 A1, 2007 ; Location in patent: Page/Page column 20 ; WO 2007/089507 A1
  • Route3
    • null|null
      118-92-3
    • ~%
    • In-stock
      3-Nitroquinolin-4-ol|CS-M2023
      50332-66-6

    References

    • Bachman et al. Journal of the American Chemical Society, 1947 , vol. 69, p. 365,370

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   76.26
  • LogP   1.8486
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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