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CS-W001157 4
Total: USD 88.00

5-Bromo-8-nitroquinoline

  • CAS No. 176967-80-9

  • Cat. No. CS-0041420
  • Purity≥97%
  • MDL No.MFCD00466078

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

5-Bromo-8-nitroquinoline|CS-0041420

Structure of 176967-80-9

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General Information

  • CAS No. 176967-80-9
  • Cat. No. CS-0041420
  • Purity ≥97%
  • MDL No. MFCD00466078
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrN₂O₂
  • Molecular Weight 253.05
  • Synonym(s) 5-Bromo-8-nitro-quinoline
  • SMILES O=[N+](C1=C2N=CC=CC2=C(Br)C=C1)[O-]

Description

5-Bromo-8-nitroquinoline delivers a potent electron-deficient heterocyclic scaffold, combining a bromine substituent at the 5-position with a nitro group at the 8-position. This configuration enables direct functionalization in cross-coupling reactions and enhances reactivity in metal-catalyzed transformations. The molecule exhibits high stability under standard conditions and serves as a key building block for advanced pharmaceutical intermediates and materials chemistry applications.

Application

5-Bromo-8-nitroquinoline serves as a versatile building block in medicinal chemistry and catalytic cross-coupling reactions. The bromo group enables palladium-catalyzed transformations such as Suzuki, Stille, and Negishi couplings, while the nitro functionality offers opportunities for selective reduction and further derivatization. Its stability under standard reaction conditions and compatibility with diverse functional groups make it a practical scaffold for constructing complex heterocyclic architectures in API development.

Synthesis

  • Route1

    References

    • US2012/214803 A1, ; Page/Page column 173 ; US 20120214803 A1
  • Route2
    • In-stock
      5-Bromoquinoline|CS-W002559
      4964-71-0
    • ~%
    • In-stock
      5-Bromo-8-nitroquinoline|CS-0041420
      176967-80-9
    • null|null
      855837-58-0

    References

    • Journal fuer Praktische Chemie (Leipzig), , vol. <2> 73, p. 249 Recueil des Travaux Chimiques des Pays-Bas, , vol. 48, p. 552 Journal fuer Praktische Chemie (Leipzig), , vol. <2> 38, p. 391 Journal fuer Praktische Chemie (Leipzig), , vol. <2> 40, p. 382
  • Route3
    • null|null
      591-19-5
    • ~%
    • In-stock
      5-Bromo-8-nitroquinoline|CS-0041420
      176967-80-9

    References

    • Journal fuer Praktische Chemie (Leipzig), , vol. <2> 38, p. 391 Journal fuer Praktische Chemie (Leipzig), , vol. <2> 40, p. 382

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   56.03
  • LogP   2.9055
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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