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5-Iodoisophthalic acid

  • CAS No. 51839-16-8

  • Cat. No. CS-0169459
  • Purity≥98%
  • MDL No.MFCD12913553

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

5-Iodoisophthalic acid|CS-0169459

Structure of 51839-16-8

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General Information

  • CAS No. 51839-16-8
  • Cat. No. CS-0169459
  • Purity ≥98%
  • MDL No. MFCD12913553
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅IO₄
  • Molecular Weight 292.03
  • Synonym(s) None
  • SMILES O=C(O)C1=CC(I)=CC(=C1)C(=O)O

Description

5-Iodoisophthalic acid features a rigid aromatic core with two carboxylic acid groups flanking a para-iodo substituent, enabling precise functionalization in cross-coupling reactions. This configuration supports efficient derivatization for bioconjugation and materials synthesis under standard conditions.

Application

5-Iodoisophthalic acid serves as a versatile building block for metal-catalyzed cross-coupling reactions, enabling efficient access to functionalized aromatic scaffolds. Its iodine substituent facilitates palladium-catalyzed coupling with boronic acids, stannanes, and amines, while the two carboxylic acid groups provide sites for derivatization, salt formation, or incorporation into polymers and bioactive molecules. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows requiring ortho-functionalized isophthalate motifs.

Synthesis

  • Route1

    References

    • Yamazaki, Manabu; Hagiwara, Toshiki; Sekiguchi, Masahiro; Sawaguchi, Takashi; Yano, Shoichiro Synthetic Communications, 2008 , vol. 38, # 4 p. 553 - 558
  • Route2

    References

    • Vaidyanathan; White; Affleck; Zhao; Welsh; McDougald; Choi; Zalutsky Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 24 p. 6929 - 6939
  • Route3

    References

    • Wessendorf, Florian; Hirsch, Andreas Tetrahedron, 2008 , vol. 64, # 50 p. 11480 - 11489

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   1.6876
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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