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CS-W001157 4
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2,4-Dibromoquinoline

  • CAS No. 20151-40-0

  • Cat. No. CS-0103202
  • Purity≥95%
  • MDL No.MFCD00837761

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

2,4-Dibromoquinoline|CS-0103202

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General Information

  • CAS No. 20151-40-0
  • Cat. No. CS-0103202
  • Purity ≥95%
  • MDL No. MFCD00837761
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅Br₂N
  • Molecular Weight 286.95
  • Synonym(s) 2,4-Dibromo-quinoline
  • SMILES BrC1=CC(Br)=NC2=CC=CC=C12

Description

2,4-Dibromoquinoline is a brominated quinoline derivative featuring two bromine atoms at the 2- and 4-positions, conferring enhanced electrophilicity and stability. This configuration enables direct use in palladium-catalyzed cross-coupling reactions, where it integrates efficiently into complex molecular architectures. The compound exhibits excellent bench-stability and compatibility with standard synthetic protocols.

Application

2,4-Dibromoquinoline serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The bromine substituents at the 2- and 4-positions exhibit high reactivity under palladium-catalyzed conditions, facilitating Suzuki, Stille, and Negishi couplings with excellent functional group tolerance. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Boudet, Nadege; Lachs, Jennifer R.; Knochel, Paul Organic Letters, 2007 , vol. 9, # 26 p. 5525 - 5528
  • Route2
    • null|null
      70254-43-2
    • ~99%
    • In-stock
      2,4-Dibromoquinoline|CS-0103202
      20151-40-0

    References

    • Reisch, Johannes; Gunaherath, G. M. Kamal B. Journal of Heterocyclic Chemistry, 1993 , vol. 30, # 4 p. 1057 - 1060
  • Route3
    • null|null
      141-82-2
    • null|null
      74497-02-2
    • ~76%
    • In-stock
      2,4-Dibromoquinoline|CS-0103202
      20151-40-0

    References

    • Osborne, Alan G.; Buley, Jill M.; Clarke, Helen; Dakin, Rachel C. H.; Price, Paul I. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993 , # 22 p. 2747 - 2756

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335
Precautionary Statements : P280-P302+P352-P330

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   3.7598
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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