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CS-W001157 4
Total: USD 88.00

2,4-Dichloro-1,8-naphthyridine

  • CAS No. 59514-89-5

  • Cat. No. CS-D0002
  • Purity≥97%
  • MDL No.MFCD00234380

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

2,4-Dichloro-1,8-naphthyridine|CS-D0002

Structure of 59514-89-5

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General Information

  • CAS No. 59514-89-5
  • Cat. No. CS-D0002
  • Purity ≥97%
  • MDL No. MFCD00234380
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄Cl₂N₂
  • Molecular Weight 199.04
  • Synonym(s) 2,4-Dichloro-pyrido[2,3-b]pyridine
  • SMILES ClC1=CC(Cl)=NC2=NC=CC=C12

Description

2,4-Dichloro-1,8-naphthyridine is a bench-stable, electron-deficient heterocycle featuring two chlorine substituents at positions 2 and 4. This configuration enhances its utility in transition metal-catalyzed cross-coupling reactions, where the chlorides serve as effective coupling partners. The fused bicyclic scaffold provides rigidity and improved solubility in common organic solvents, facilitating integration into complex molecular architectures.

Application

2,4-Dichloro-1,8-naphthyridine serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its electron-deficient heterocyclic core exhibits excellent bench stability and compatibility with diverse nucleophiles, facilitating the construction of biologically active scaffolds. The dichloro substitution pattern provides orthogonal reactivity for sequential derivatization, making it particularly valuable in API development workflows requiring precise structural control.

Synthesis

  • Route1
    • 2,4-Dihydroxy-1,8-naphthyridine|CS-0029741
      59514-86-2
    • ~%
    • In-stock
      2,4-Dichloro-1,8-naphthyridine|CS-D0002
      59514-89-5

    References

    • WO2012/595 A1, ; Page/Page column 74 ; WO 2012/000595 A1
  • Route2
    • 1-Benzyl-4-hydroxy-1,8-naphthyridin-2(1h)-one|CS-0682594
      219775-95-8
    • ~28%
    • In-stock
      2,4-Dichloro-1,8-naphthyridine|CS-D0002
      59514-89-5
    • 1-Benzyl-4-chloro-1,8-naphthyridin-2(1H)-one|CS-0594381
      583031-57-6

    References

    • WO2008/24423 A2, ; Page/Page column 43 ;
  • Route3

    References

    • WO2012/595 A1, ; WO 2012/000595 A1

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   25.78
  • LogP   2.9366
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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