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Methyl 3-bromo-2-hydroxybenzoate

  • CAS No. 28165-45-9

  • Cat. No. CS-W022823
  • Purity≥97%
  • MDL No.MFCD10566798

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

Methyl 3-bromo-2-hydroxybenzoate|CS-W022823

Structure of 28165-45-9

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General Information

  • CAS No. 28165-45-9
  • Cat. No. CS-W022823
  • Purity ≥97%
  • MDL No. MFCD10566798
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO₃
  • Molecular Weight 231.04
  • Synonym(s) Methyl 3-bromosalicylate
  • SMILES O=C(OC)C1=CC=CC(Br)=C1O

Description

Methyl 3-bromo-2-hydroxybenzoate features a bromine atom at the meta position relative to the ester, paired with a hydroxyl group ortho to the carbonyl. This dual functionalization enables direct coupling in cross-coupling reactions and facilitates derivatization through the phenolic OH. The compound exhibits good stability under standard bench conditions and integrates readily into synthetic sequences requiring halogenated aromatic intermediates.

Application

Methyl 3-bromo-2-hydroxybenzoate serves as a versatile building block in medicinal chemistry and synthetic organic synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other heterocyclic scaffolds. The ortho-hydroxyl group facilitates intramolecular cyclization, while the bromide supports palladium-catalyzed cross-coupling reactions. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step sequences requiring functional group compatibility and positional control.

Synthesis

  • Route1

    References

    • Bovonsombat, Pakorn; Ali, Rameez; Khan, Chiraphorn; Leykajarakul, Juthamard; Pla-On, Kawin; Aphimanchindakul, Suraj; Pungcharoenpong, Natchapon; Timsuea, Nisit; Arunrat, Anchalee; Punpongjareorn, Napat Tetrahedron, 2010 , vol. 66, # 34 p. 6928 - 6935
  • Route2
    • null|null
      67-56-1
    • null|null
      854914-90-2
    • ~99%
    • In-stock
      Methyl 3-bromo-2-hydroxybenzoate|CS-W022823
      28165-45-9

    References

    • Dobler, Markus R. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 7 p. 963 - 964
  • Route3
    • null|null
      95-56-7
    • ~%
    • In-stock
      Methyl 3-bromo-2-hydroxybenzoate|CS-W022823
      28165-45-9

    References

    • Dobler, Markus R. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 7 p. 963 - 964

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   46.53
  • LogP   1.9413
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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