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CS-W001157 4
Total: USD 88.00

3-Cyano-4-hydroxybenzoic acid methyl ester

  • CAS No. 156001-68-2

  • Cat. No. CS-0033761
  • Purity≥95%
  • MDL No.MFCD13248596

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

3-Cyano-4-hydroxybenzoic acid methyl ester|CS-0033761

Structure of 156001-68-2

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General Information

  • CAS No. 156001-68-2
  • Cat. No. CS-0033761
  • Purity ≥95%
  • MDL No. MFCD13248596
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₃
  • Molecular Weight 177.16
  • Synonym(s) Methyl 3-cyano-4-hydroxybenzoate
  • SMILES O=C(OC)C1=CC=C(O)C(C#N)=C1

Description

This methyl ester derivative features a cyano group at the meta position and a hydroxyl substituent at the para position relative to the carboxylic acid ester, enabling precise tuning of electronic properties and solubility. The ortho-ester functionality enhances reactivity in coupling reactions, while the phenolic hydroxyl supports hydrogen bonding and derivatization. Designed for synthetic applications requiring balanced polarity and stability under standard conditions.

Application

3-Cyano-4-hydroxybenzoic acid methyl ester serves as a versatile building block for heterocyclic synthesis and medicinal chemistry campaigns. Its orthogonal functionality—cyano, phenolic hydroxyl, and ester groups—enables sequential transformations including cyclization, amidation, and nucleophilic addition. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for scale-up and multi-step synthetic sequences in API development.

Synthesis

  • Route1
    • In-stock
      Methyl 4-hydroxy-3-iodobenzoate|CS-W019910
      15126-06-4
    • null|null
      143-33-9
    • null|null
      544-92-3
    • ~99%
    • In-stock
      3-Cyano-4-hydroxybenzoic acid methyl ester|CS-0033761
      156001-68-2

    References

    • CYTOKINETICS, INC.; SMITHKLINE BEECHAM CORPORATION Patent: WO2005/107762 A2, 2005 ; Location in patent: Page/Page column 253-254 ;
  • Route2
    • In-stock
      Methyl 4-hydroxy-3-iodobenzoate|CS-W019910
      15126-06-4
    • null|null
      143-33-9
    • ~71%
    • In-stock
      3-Cyano-4-hydroxybenzoic acid methyl ester|CS-0033761
      156001-68-2

    References

    • Madsen, Peter; Ling, Anthony; Plewe, Michael; Sams, Christian K.; Knudsen, Lotte B.; Sidelmann, Ulla G.; Ynddal, Lars; Brand, Christian L.; Andersen, Birgitte; Murphy, Douglas; Teng, Min; Truesdale, Larry; Kiel, Dan; May, John; Kuki, Atsuo; Shi, Shenghua; Johnson, Michael D.; Teston, Kimberly Ann; Feng, Jun; Lakis, James; Anderes, Kenna; Gregor, Vlad; Lau, Jesper Journal of Medicinal Chemistry, 2002 , vol. 45, # 26 p. 5755 - 5775
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 45, # 26 p. 5755 - 5775

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   70.32
  • LogP   1.05048
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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