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5-Iodoindolin-2-one

  • CAS No. 193354-13-1

  • Cat. No. CS-M1385
  • Molecule weight259.05
  • Purity≥95%
  • MDL No.MFCD08669500

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

5-Iodoindolin-2-one|CS-M1385

Structure of 193354-13-1

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General Information

  • CAS No. 193354-13-1
  • Cat. No. CS-M1385
  • Purity ≥95%
  • MDL No. MFCD08669500
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆INO
  • Molecular Weight 259.05
  • Synonym(s) 5-iodo-2,3-dihydro-1H-indol-2-one
  • SMILES O=C1NC2=CC=C(I)C=C2C1

Description

5-Iodoindolin-2-one delivers a reactive iodine handle at the 5-position of the indolin-2-one scaffold, enabling efficient late-stage functionalization in medicinal chemistry. This bench-stable, moisture-tolerant compound integrates readily into cross-coupling workflows, facilitating the construction of diverse heterocyclic architectures with high functional group compatibility.

Application

5-Iodoindolin-2-one serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biologically relevant indole scaffolds. The iodine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the indolin-2-one core offers inherent stability and compatibility with diverse functional groups. Its bench-stable nature and straightforward purification facilitate integration into multi-step syntheses of targeted compounds.

Synthesis

  • Route1

    References

    • Alanine, Alexander; Buettelmann, Bernd; Neidhart, Marie-Paule H.; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene Patent: US2001/47031 A1, 2001 ; US 20010047031 A1
  • Route2

    References

    • Bouchikhi, Fadoua; Anizon, Fabrice; Moreau, Pascale European Journal of Medicinal Chemistry, 2008 , vol. 43, # 4 p. 755 - 762
  • Route3

    References

    • Jha, Mukund; Chou, Ting-Yi; Blunt, Brian Tetrahedron, 2011 , vol. 67, # 5 p. 982 - 989

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

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   1.7858
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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