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CS-W001157 4
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2-Iodobenzenesulfonic acid

  • CAS No. 63059-25-6

  • Cat. No. CS-0041161
  • Purity95% (sodium)
  • MDL No.MFCD01860232

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

2-Iodobenzenesulfonic acid|CS-0041161

Structure of 63059-25-6

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General Information

  • CAS No. 63059-25-6
  • Cat. No. CS-0041161
  • Purity 95% (sodium)
  • MDL No. MFCD01860232
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅IO₃S
  • Molecular Weight 284.07
  • Synonym(s) 2-Iodobenzenesulphonic acid; 2-Iodobenzenesulfonic acid
  • SMILES O=S(C1=CC=CC=C1I)(O)=O

Description

2-Iodobenzenesulfonic acid delivers a reactive iodine handle ortho to a sulfonic acid group, enabling site-specific functionalization in cross-coupling and derivatization workflows. The electron-withdrawing sulfonic moiety enhances halogen reactivity while maintaining solubility in polar media. This robust, bench-stable reagent facilitates efficient incorporation into complex molecular architectures under standard conditions.

Application

2-Iodobenzenesulfonic acid serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling the efficient installation of aryl sulfonate motifs. Its iodine functionality facilitates palladium-catalyzed coupling with boronic acids and amines, while the sulfonic acid group provides enhanced solubility and stability under reaction conditions. The ortho-iodo substitution pattern supports selective transformations, making it valuable for constructing biaryl architectures and functionalized heterocycles in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Chemische Berichte, , vol. 28, p. 91 Justus Liebigs Annalen der Chemie, , vol. 186, p. 325
  • Route2

    References

    • Justik, Michael W.; Protasiewicz, John D.; Updegraff, James B. Tetrahedron Letters, 2009 , vol. 50, # 44 p. 6072 - 6075

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   54.37
  • LogP   1.5379
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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