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2-Bromoisophthalic acid

  • CAS No. 22433-91-6

  • Cat. No. CS-0168202
  • Purity≥95%
  • MDL No.MFCD00099229

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

2-Bromoisophthalic acid|CS-0168202

Structure of 22433-91-6

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General Information

  • CAS No. 22433-91-6
  • Cat. No. CS-0168202
  • Purity ≥95%
  • MDL No. MFCD00099229
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrO₄
  • Molecular Weight 245.03
  • Synonym(s) 2-Bromobenzene-1,3-dicarboxylic acid
  • SMILES O=C(O)C1=CC=CC(C(=O)O)=C1Br

Description

2-Bromoisophthalic acid features a bromine substituent at the aromatic ring, enhancing its reactivity in cross-coupling transformations. This ortho-disubstituted benzoic acid derivative offers improved solubility and stability compared to non-halogenated analogs, facilitating efficient incorporation into pharmaceutical intermediates and functional materials under standard conditions.

Application

2-Bromoisophthalic acid serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the aromatic ring and carboxylic acid termini. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, while the ortho-dicarboxylic acid framework supports metal coordination and derivatization for heterocycle synthesis. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for use in medicinal chemistry lead optimization and materials science applications.

Synthesis

  • Route1

    References

    • ANACOR PHARMACEUTICALS, INC.; ZHOU, Huchen; DING, Dazhong; ZHOU, Yasheen; ZHANG, Yong-Kang; PLATTNER, Jacob J. Patent: WO2011/22337 A1, 2011 ; Location in patent: Page/Page column 66 ;
  • Route2

    References

    • Coulson Journal of the Chemical Society, 1937 , p. 1298,1304
  • Route3

    References

    • Helmchen,G.; Prelog,V. Helvetica Chimica Acta, 1972 , vol. 55, p. 2599 - 2611

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   1.8455
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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