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

  • CAS No. 58380-11-3

  • Cat. No. CS-W018588
  • Purity≥96%
  • MDL No.None

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

2-Bromo-5-hydroxybenzoic acid|CS-W018588

Structure of 58380-11-3

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General Information

  • CAS No. 58380-11-3
  • Cat. No. CS-W018588
  • Purity ≥96%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrO₃
  • Molecular Weight 217.02
  • Synonym(s) benzoic acid, 2-bromo-5-hydroxy-
  • SMILES O=C(O)C1=CC(O)=CC=C1Br

Description

2-Bromo-5-hydroxybenzoic acid features a bromine atom at the ortho position relative to the carboxylic acid, combined with a hydroxyl group para to the acid. This dual functionality enables selective coupling reactions in synthetic pathways. The molecule exhibits enhanced reactivity in nucleophilic aromatic substitution due to the electron-withdrawing carboxylic acid and bromine, while the phenolic hydroxyl supports hydrogen bonding and solubility in polar media.

Application

2-Bromo-5-hydroxybenzoic acid serves as a versatile building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. The ortho-bromo and para-hydroxy groups enable sequential functionalization via palladium-catalyzed cross-coupling and electrophilic substitution reactions. Its bench-stable nature and compatibility with common protecting group strategies facilitate efficient multi-step synthesis, particularly in the construction of substituted benzofurans and arylated phenolic scaffolds.

Synthesis

  • Route1

    References

    • Yakugaku Zasshi, , vol. 76, p. 1122,1125 Chem.Abstr., , p. 3505
  • Route2

    References

    • Recueil des Travaux Chimiques des Pays-Bas, , vol. 40, p. 630
  • Route3

    References

    • Chemische Berichte, , vol. 62, p. 1182 Chemische Berichte, , vol. 66, p. 1761,1762

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   57.53
  • LogP   1.8529
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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