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CS-W001157 4
Total: USD 88.00

2,7-Dichloro-1,8-naphthyridine

  • CAS No. 55243-02-2

  • Cat. No. CS-0133252
  • Molecule weight199.04
  • Purity≥97%
  • MDL No.MFCD08234796

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

2,7-Dichloro-1,8-naphthyridine|CS-0133252

Structure of 55243-02-2

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General Information

  • CAS No. 55243-02-2
  • Cat. No. CS-0133252
  • Purity ≥97%
  • MDL No. MFCD08234796
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄Cl₂N₂
  • Molecular Weight 199.04
  • Synonym(s) 1,8-naphthyridine, 2,7-dichloro-
  • SMILES ClC1=CC=C2C=CC(Cl)=NC2=N1

Description

2,7-Dichloro-1,8-naphthyridine is a bench-stable, electron-deficient heterocycle featuring two chlorine substituents at key positions. This configuration enhances its reactivity in transition-metal-catalyzed couplings and enables efficient incorporation into pharmaceutical intermediates. The molecule’s planar structure supports π-stacking interactions, making it valuable in materials science applications.

Application

2,7-Dichloro-1,8-naphthyridine serves as a versatile building block in medicinal chemistry and catalytic synthesis, enabling efficient functionalization at nitrogen-rich heterocyclic sites. Its dichloro substitution pattern facilitates palladium-catalyzed cross-coupling reactions and nucleophilic aromatic substitution, offering predictable regioselectivity. The compound exhibits excellent bench stability and compatibility with diverse reaction conditions, making it well-suited for constructing complex scaffolds in API development and materials science applications.

Synthesis

  • Route1
    • 1,8-Naphthyridine-2,7-diol|CS-0171174
      49655-93-8
    • ~78%
    • In-stock
      2,7-Dichloro-1,8-naphthyridine|CS-0133252
      55243-02-2

    References

    • Newkome, George R.; Garbis, Sam J.; Majestic, Veronica K.; Fronczek, Frank R.; Chiari, Giacomo Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 833 - 839
  • Route2
    • In-stock
      2,6-Diaminopyridine|CS-W020019
      141-86-6
    • null|null
      617-48-1
    • ~%
    • In-stock
      2,7-Dichloro-1,8-naphthyridine|CS-0133252
      55243-02-2

    References

    • Synlett, , vol. 24, # 3 art. no. ST-2012-D1044-L, p. 359 - 362
  • Route3

    References

    • Journal of the Chemical Society - Dalton Transactions, , # 23 p. 4561 - 4570

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-P330-P362+P364-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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