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CS-W001157 4
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1-Iodoisoquinoline

  • CAS No. 19658-77-6

  • Cat. No. CS-0171441
  • Purity≥98%
  • MDL No.None

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

1-Iodoisoquinoline|CS-0171441

Structure of 19658-77-6

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General Information

  • CAS No. 19658-77-6
  • Cat. No. CS-0171441
  • Purity ≥98%
  • 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) isoquinoline,1-iodo
  • SMILES C1=CC=C2C(=C1)C=CN=C2I

Description

1-Iodoisoquinoline is a bench-stable, electron-deficient heterocycle featuring a reactive iodine atom at the isoquinoline core. This substitution pattern enables direct coupling in cross-coupling reactions, facilitating efficient access to functionalized isoquinoline derivatives under standard conditions.

Application

1-Iodoisoquinoline serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to construct biaryl and heteroaryl scaffolds. Its iodine functionality offers high reactivity under standard Suzuki, Stille, and Negishi conditions, facilitating efficient C–C bond formation. The molecule exhibits good bench stability and compatibility with diverse functional groups, making it a practical choice for medicinal chemistry campaigns and the synthesis of complex nitrogen-containing heterocycles.

Synthesis

  • Route1

    References

    • Clayden, Jonathan; Fletcher, Stephen P.; McDouall, Joseph J. W.; Rowbottom, Stephen J. M. Journal of the American Chemical Society, 2009 , vol. 131, p. 5331 - 5343
  • Route2

    References

    • Kadiyala, Raghu Ram; Tilly, David; Nagaradja, Elisabeth; Roisnel, Thierry; Matulis, Vadim E.; Ivashkevich, Oleg A.; Halauko, Yury S.; Chevallier, Floris; Gros, Philippe C.; Mongin, Florence Chemistry - A European Journal, 2013 , vol. 19, # 24 p. 7944 - 7960
  • Route3
    • null|null
      1161941-05-4
    • ~95%
    • In-stock
      1-Iodoisoquinoline|CS-0171441
      19658-77-6

    References

    • Bissember, Alex C.; Banwell, Martin G. Journal of Organic Chemistry, 2009 , vol. 74, # 13 p. 4893 - 4895

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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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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