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CS-W001157 4
Total: USD 88.00

5-Ethynyl-2-hydroxybenzaldehyde

  • CAS No. 252771-08-7

  • Cat. No. CS-0170753
  • Purity≥98%
  • MDL No.MFCD18824475

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

5-Ethynyl-2-hydroxybenzaldehyde|CS-0170753

Structure of 252771-08-7

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General Information

  • CAS No. 252771-08-7
  • Cat. No. CS-0170753
  • Purity ≥98%
  • MDL No. MFCD18824475
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆O₂
  • Molecular Weight None
  • Synonym(s) Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI)
  • SMILES O=CC1=CC(C#C)=CC=C1O

Description

5-Ethynyl-2-hydroxybenzaldehyde features a conjugated alkyne tethered to a phenolic aldehyde, enabling efficient copper-catalyzed azide-alkyne cycloaddition. The hydroxyl group enhances solubility and directs regiochemistry in coupling reactions. This bifunctional scaffold supports modular synthesis of bioactive heterocycles and functionalized aromatic systems under mild conditions.

Application

5-Ethynyl-2-hydroxybenzaldehyde serves as a versatile building block for copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, enabling efficient access to triazole-linked scaffolds. The molecule combines an aldehyde functionality with a terminal alkyne and phenolic hydroxyl group, offering orthogonal reactivity for sequential conjugations. Its bench-stable nature and compatibility with standard protecting group strategies facilitate integration into multi-step synthetic sequences, particularly in the construction of functionalized heterocycles and bioactive compound libraries.

Synthesis

  • Route1
    • null|null
      727375-48-6
    • ~93%
    • In-stock
      5-Ethynyl-2-hydroxybenzaldehyde|CS-0170753
      252771-08-7

    References

    • Beyer, Christoph; Wagenknecht, Hans-Achim Journal of Organic Chemistry, 2010 , vol. 75, # 8 p. 2752 - 2755
  • Route2

    References

    • Chang, Ku-Hsien; Huang, Chiung-Cheng; Liu, Yi-Hung; Hu, Ya-Hui; Chou, Pi-Tai; Lin, Ying-Chih Dalton Transactions, 2004 , # 11 p. 1731 - 1738

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 : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   1.186
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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