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CS-W001157 4
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5-Bromo-2-iodobenzoic acid

  • CAS No. 21740-00-1

  • Cat. No. CS-W002338
  • Purity≥98%
  • MDL No.MFCD00079717

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

5-Bromo-2-iodobenzoic acid|CS-W002338

Structure of 21740-00-1

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General Information

  • CAS No. 21740-00-1
  • Cat. No. CS-W002338
  • Purity ≥98%
  • MDL No. MFCD00079717
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrIO₂
  • Molecular Weight 326.91
  • Synonym(s) None
  • SMILES BrC1=CC(C(O)=O)=C(I)C=C1

Description

5-Bromo-2-iodobenzoic acid features a benzoic acid core functionalized with bromo and iodo substituents at the meta and ortho positions, respectively. This dual halogenation enables efficient cross-coupling transformations in synthetic routes. The carboxylic acid group facilitates derivatization and incorporation into bioactive scaffolds. Designed for use in medicinal chemistry and materials synthesis, this compound offers high reactivity under standard palladium-catalyzed conditions.

Application

5-Bromo-2-iodobenzoic acid serves as a versatile dihalogenated aromatic building block for palladium-catalyzed cross-coupling reactions. The bromo and iodo groups enable sequential functionalization via orthogonal reactivity, facilitating the assembly of complex biaryl architectures. Its carboxylic acid functionality offers direct handle for derivatization, while maintaining bench stability and compatibility with standard purification protocols in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1

    References

    • Ravnsbaek, Jens B.; Jacobsen, Mikkel F.; Rosen, Christian B.; Voigt, Niels V.; Gothelf, Kurt V. Angewandte Chemie - International Edition, 2011 , vol. 50, # 46 p. 10851 - 10854
  • Route2

    References

    • Chemische Berichte, , vol. 29, p. 1410
  • Route3

    References

    • Stock, Nicholas; Volkots, Deborah; Stebbins, Karin; Broadhead, Alex; Stearns, Brian; Roppe, Jeffrey; Parr, Timothy; Baccei, Christopher; Bain, Gretchen; Chapman, Charles; Correa, Lucia; Darlington, Janice; King, Christopher; Lee, Catherine; Lorrain, Daniel S.; Prodanovich, Pat; Santini, Angelina; Evans, Jilly F.; Hutchinson, John H.; Prasit, Peppi Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 3 p. 1036 - 1040

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   37.3
  • LogP   2.7519
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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