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CS-W001157 4
Total: USD 88.00

6-Bromo-8-nitroquinoline

  • CAS No. 68527-67-3

  • Cat. No. CS-0041422
  • Purity≥97%
  • MDL No.MFCD09907842

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

6-Bromo-8-nitroquinoline|CS-0041422

Structure of 68527-67-3

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General Information

  • CAS No. 68527-67-3
  • Cat. No. CS-0041422
  • Purity ≥97%
  • MDL No. MFCD09907842
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrN₂O₂
  • Molecular Weight 253.05
  • Synonym(s) Quinoline, 6-bromo-8-nitro-
  • SMILES O=[N+](C1=C2N=CC=CC2=CC(Br)=C1)[O-]

Description

6-Bromo-8-nitroquinoline features a quinoline core functionalized with bromine at the 6-position and a nitro group at the 8-position, creating a highly electron-deficient heteroaromatic system. This combination enables efficient coupling reactions in cross-coupling protocols and facilitates direct functionalization in synthetic sequences. The molecule exhibits excellent stability under standard conditions and serves as a key intermediate in medicinal chemistry and materials science applications.

Application

6-Bromo-8-nitroquinoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its ortho-halogen and electron-deficient quinoline framework. The nitro group provides a handle for selective reduction or further functionalization, while the bromine facilitates reliable Suzuki, Stille, or Negishi couplings. Bench-stable and readily purified by recrystallization, it functions efficiently in the construction of complex heterocyclic scaffolds relevant to kinase inhibitors and other bioactive molecules.

Synthesis

  • Route1

    References

    • Wyeth Patent: EP1147083 B1, 2004 ; Location in patent: Page 45-46 ; EP 1147083 B1
  • Route2
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    • In-stock
      6-Bromo-8-nitroquinoline|CS-0041422
      68527-67-3

    References

    • Journal of the American Chemical Society, , vol. 72, p. 393
  • Route3
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    • ~%
    • In-stock
      6-Bromo-8-nitroquinoline|CS-0041422
      68527-67-3

    References

    • Monatshefte fuer Chemie, , vol. 125, # 6/7 p. 723 - 730

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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