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Methyl 4-formyl-3-hydroxybenzoate

  • CAS No. 24589-98-8

  • Cat. No. CS-0044168
  • Purity≥97%
  • MDL No.MFCD17015455

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

Methyl 4-formyl-3-hydroxybenzoate|CS-0044168

Structure of 24589-98-8

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General Information

  • CAS No. 24589-98-8
  • Cat. No. CS-0044168
  • Purity ≥97%
  • MDL No. MFCD17015455
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈O₄
  • Molecular Weight 180.16
  • Synonym(s) methyl 4-formyl-3-hydoxybenzoate
  • SMILES COC(C1=CC=C(C=O)C(O)=C1)=O

Description

Methyl 4-formyl-3-hydroxybenzoate features a strategically positioned aldehyde and phenolic hydroxyl group, enabling direct functionalization in synthetic sequences. The ester moiety enhances solubility in organic solvents while maintaining compatibility with diverse reaction conditions. This scaffold serves as a key intermediate for bioactive molecule synthesis, particularly in medicinal chemistry and natural product derivatization.

Application

Methyl 4-formyl-3-hydroxybenzoate serves as a versatile synthetic intermediate for the construction of bioactive heterocycles and functionalized aromatic scaffolds. The ortho-hydroxyl and aldehyde functionalities enable efficient intramolecular cyclization, while the ester group provides a handle for selective derivatization. Its bench-stable nature and compatibility with standard coupling and reduction protocols facilitate straightforward incorporation into complex molecular architectures relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      4-Formyl-3-hydroxybenzoic acid|CS-W007759
      619-12-5
    • ~99%
    • In-stock
      Methyl 4-formyl-3-hydroxybenzoate|CS-0044168
      24589-98-8

    References

    • CHIESI FARMACEUTICI S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Esposito, Oriana; Carzaniga, Laura; Capaldi, Carmelida Patent: US2014/155391 A1, 2014 ; Location in patent: Paragraph 0617; 0618 ;
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    References

    • Harayama; Nakatsuka; Nishioka; Murakami; Hayashida; Ishii Chemical and Pharmaceutical Bulletin, 1994 , vol. 42, # 10 p. 2170 - 2173
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    References

    • Inoue, Seiichi; Yanai, Takayoshi; Ando, Shinji; Nakazawa, Akinori; Honda, Kiyoshi; Hoshino, Yujiro; Asai, Tomoyuki Journal of Materials Chemistry, 2005 , vol. 15, # 44 p. 4746 - 4752

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   63.6
  • LogP   0.9913
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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