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CS-W001157 4
Total: USD 88.00

5-Iodoquinoline

  • CAS No. 1006-50-4

  • Cat. No. CS-0440178
  • Molecule weight255.06
  • Purity≥97%
  • MDL No.None

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

5-Iodoquinoline|CS-0440178

Structure of 1006-50-4

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General Information

  • CAS No. 1006-50-4
  • Cat. No. CS-0440178
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆IN
  • Molecular Weight 255.06
  • Synonym(s) None
  • SMILES C1=CC(=C2C=CC=NC2=C1)I

Description

5-Iodoquinoline is a halogenated quinoline derivative featuring a reactive iodine substituent at the 5-position, enabling direct functionalization in cross-coupling reactions. This electron-deficient heterocycle serves as a key scaffold in medicinal chemistry and materials science, offering enhanced stability under standard conditions while maintaining high reactivity in palladium-catalyzed transformations.

Application

5-Iodoquinoline serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The iodine substituent provides high reactivity in Pd- and Ni-catalyzed coupling processes, while the quinoline core offers favorable electronic properties and stability under standard reaction conditions. Its bench-stable nature and compatibility with diverse functional groups make it a practical choice for synthetic medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Karramkam, Mylene; Dolle, Frederic; Valette, Heric; Besret, Laurent; Bramoulle, Yann; Hinnen, Francoise; Vaufrey, Francoise; Franklin, Carine; Bourg, Sebastien; Coulon, Christine; Ottaviani, Michele; Delaforge, Marcel; Loc'h, Christian; Bottlaender, Michel; Crouzel, Christian Bioorganic and medicinal chemistry, 2002 , vol. 10, # 8 p. 2611 - 2623
  • Route2
    • null|null
      67-56-1
    • In-stock
      Quinolin-5-amine|CS-W001604
      611-34-7
    • ~19%
    • In-stock
      5-Iodoquinoline|CS-0440178
      1006-50-4

    References

    • Lautens, Mark; Paquin, Jean-Francois; Piguel, Sandrine Journal of Organic Chemistry, 2002 , vol. 67, # 11 p. 3972 - 3974
  • Route3
    • null|null
      91-22-5
    • ~%
    • In-stock
      5-Iodoquinoline|CS-0440178
      1006-50-4

    References

    • Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 127, p. 521

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   12.89
  • LogP   2.8394
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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