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CS-W001157 4
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8-Nitroquinolin-6-ol

  • CAS No. 5437-99-0

  • Cat. No. CS-0162614
  • Purity≥96%
  • MDL No.None

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

8-Nitroquinolin-6-ol|CS-0162614

Structure of 5437-99-0

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General Information

  • CAS No. 5437-99-0
  • Cat. No. CS-0162614
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆N₂O₃
  • Molecular Weight 190.16
  • Synonym(s) 6-Quinolinol,8-nitro-
  • SMILES OC1=CC([N+]([O-])=O)=C2N=CC=CC2=C1

Description

8-Nitroquinolin-6-ol delivers a potent electron-deficient heterocyclic scaffold ideal for transition metal-catalyzed coupling reactions. The para-nitro group enhances reactivity in cross-coupling processes, while the phenolic hydroxyl enables direct functionalization or coordination to metal centers. This bench-stable compound integrates seamlessly into synthetic sequences requiring precise electronic tuning and structural rigidity.

Application

8-Nitroquinolin-6-ol serves as a versatile scaffold for medicinal chemistry and materials science, enabling direct functionalization at the 2- and 4-positions via electrophilic substitution. The nitro group enhances reactivity in cross-coupling reactions, while the hydroxyl moiety provides a handle for derivatization or metal chelation. Its bench-stable crystalline form facilitates handling and purification, making it a practical building block for heterocyclic libraries and advanced synthesis workflows.

Synthesis

  • Route1

    References

    • METHYLGENE INC. Patent: US2007/293530 A1, 2007 ; Location in patent: Page/Page column 84 ; US 20070293530 A1
  • Route2
    • 6-Ethoxy-8-nitroquinoline|CS-1162060
      282547-59-5
    • ~%
    • In-stock
      8-Nitroquinolin-6-ol|CS-0162614
      5437-99-0

    References

    • Morgan; Cretcher Journal of the American Chemical Society, 1946 , vol. 68, p. 781,783 Full Text Show Details Magidson; Strukow Zhurnal Obshchei Khimii, 1933 , vol. 3, p. 769,776 Archiv der Pharmazie (Weinheim, Germany), 1933 , vol. 271, p. 359,364 Chem. Zentralbl., 1934 , vol. 105, # II p. 2227
  • Route3
    • In-stock
      4-Amino-3-nitrophenol|CS-D1352
      610-81-1
    • null|null
      107-02-8
    • ~18%
    • In-stock
      8-Nitroquinolin-6-ol|CS-0162614
      5437-99-0

    References

    • McQuade, Lindsey E.; Lippard, Stephen J. Inorganic Chemistry, 2010 , vol. 49, # 20 p. 9535 - 9545

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

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