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CS-W001157 4
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6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one

  • CAS No. 129686-16-4

  • Cat. No. CS-W019255
  • Purity≥98%
  • MDL No.MFCD05664027

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

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one|CS-W019255

Structure of 129686-16-4

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General Information

  • CAS No. 129686-16-4
  • Cat. No. CS-W019255
  • Purity ≥98%
  • MDL No. MFCD05664027
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrN₂O
  • Molecular Weight 227.06
  • Synonym(s) 6-Bromo-3,4-dihydro-1H-[1,8]naphthyrid-2-one
  • SMILES BrC2=CN=C1NC(CCC1=C2)=O

Description

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one is a bench-stable heterocyclic building block featuring a brominated naphthyridinone core. This electron-deficient scaffold integrates readily into transition-metal-catalyzed coupling reactions, enabling efficient access to functionalized fused ring systems in medicinal chemistry and materials development.

Application

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one serves as a versatile building block for the synthesis of bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromo functionality. The dihydronaphthyridinone core exhibits bench stability and functional group tolerance, facilitating downstream derivatization in medicinal chemistry campaigns. Its structure supports integration into kinase inhibitor scaffolds and other pharmaceutical candidates via standard coupling protocols.

Synthesis

  • Route1
    • Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate|CS-0048943
      335031-10-2
    • ~90%
    • In-stock
      6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one|CS-W019255
      129686-16-4

    References

    • Affinium Pharmaceuticals, Inc. Patent: EP1226138 B1, 2004 ;
  • Route2
    • null|null
      1443988-87-1
    • ~91%
    • In-stock
      6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one|CS-W019255
      129686-16-4

    References

    • Zhou, Jun; Li, Bo; Hu, Fang; Shi, Bing-Feng Organic Letters, 2013 , vol. 15, # 13 p. 3460 - 3463
  • Route3

    References

    • Organic Letters, , vol. 15, # 13 p. 3460 - 3463

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   41.99
  • LogP   1.7288
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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