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CS-W001157 4
Total: USD 88.00

3-Bromo-1,5-naphthyridine

  • CAS No. 17965-71-8

  • Cat. No. CS-W021848
  • Purity≥96%
  • MDL No.MFCD11858569

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

3-Bromo-1,5-naphthyridine|CS-W021848

Structure of 17965-71-8

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General Information

  • CAS No. 17965-71-8
  • Cat. No. CS-W021848
  • Purity ≥96%
  • MDL No. MFCD11858569
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂
  • Molecular Weight 209.04
  • Synonym(s) 1,5-Naphthyridine, 3-bromo-
  • SMILES BrC1=CC2=NC=CC=C2N=C1

Description

3-Bromo-1,5-naphthyridine offers a reactive halogen site for cross-coupling reactions, enabling efficient integration into complex heterocyclic architectures. This bench-stable derivative features a planar, electron-deficient core that enhances regioselective functionalization in transition-metal-catalyzed processes.

Application

3-Bromo-1,5-naphthyridine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to construct biaryl and heteroaryl architectures. The bromine substituent exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the naphthyridine core provides excellent stability and functional group tolerance. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • WO2011/149937 A1, ; Page/Page column 39; 75 ; WO 2011/149937 A1
  • Route2
    • In-stock
      1,5-Naphthyridine|CS-B0780
      254-79-5
    • ~35%
    • 3,7-Dibromo-1,5-naphthyridine|CS-B0785
      17965-72-9
    • In-stock
      3-Bromo-1,5-naphthyridine|CS-W021848
      17965-71-8

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 23 p. 6525 - 6528
  • Route3

    References

    • ChemMedChem, , vol. 9, # 1 p. 217 - 232

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

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Computational Chemistry Data

  • TPSA   25.78
  • LogP   2.3923
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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