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CS-W001157 4
Total: USD 88.00

6-Nitroquinolin-8-ol

  • CAS No. 16727-28-9

  • Cat. No. CS-0074265
  • Molecule weight190.16
  • Purity≥97%
  • MDL No.MFCD00466084

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

6-Nitroquinolin-8-ol|CS-0074265

Structure of 16727-28-9

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General Information

  • CAS No. 16727-28-9
  • Cat. No. CS-0074265
  • Purity ≥97%
  • MDL No. MFCD00466084
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆N₂O₃
  • Molecular Weight 190.16
  • Synonym(s) 8-HYDROXY-6-NITROQUINOLINE
  • SMILES [O-][N+](C1=CC2=CC=CN=C2C(O)=C1)=O

Description

6-Nitroquinolin-8-ol delivers a potent electron-deficient quinoline scaffold bearing a strategically positioned nitro group at the 6-position and a phenolic hydroxyl at the 8-position. This combination enables strong metal chelation, enhanced solubility in polar solvents, and robust reactivity in transition-metal-catalyzed transformations under standard conditions.

Application

6-Nitroquinolin-8-ol serves as a versatile heterocyclic building block for medicinal chemistry and materials science. Its dual functionality—nitro group at C6 and hydroxyl at C8—enables selective derivatization via nucleophilic substitution, metal-catalyzed coupling, or electrophilic modification. The molecule exhibits good bench stability and facilitates access to quinoline-based scaffolds relevant in kinase inhibitor development and fluorescent probe design.

Synthesis

  • Route1
    • 8-Methoxy-6-nitroquinoline|CS-0035891
      80912-11-4
    • ~68%
    • In-stock
      6-Nitroquinolin-8-ol|CS-0074265
      16727-28-9

    References

    • Khan, Zafar U.; Patel, Dalpat I.; Smalley, Robert K.; Scriven, Eric F.V.; Suschitzky, Hans Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 10 p. 2495 - 2500
  • Route2
    • In-stock
      Glycerol|CS-6964
      56-81-5
    • null|null
      121-88-0
    • ~%
    • In-stock
      6-Nitroquinolin-8-ol|CS-0074265
      16727-28-9

    References

    • Archiv der Pharmazie (Weinheim, Germany), , vol. 291, p. 168,175

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

Quality Control

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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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