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CS-W001157 4
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4-Hydroxybut-2-ynoic acid

  • CAS No. 7218-52-2

  • Cat. No. CS-0005249
  • Purity≥98%
  • MDL No.MFCD06658457

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

4-Hydroxybut-2-ynoic acid|CS-0005249

Structure of 7218-52-2

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General Information

  • CAS No. 7218-52-2
  • Cat. No. CS-0005249
  • Purity ≥98%
  • MDL No. MFCD06658457
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₄O₃
  • Molecular Weight 100.07
  • Synonym(s) 4-HYDROXY-BUT-2-YNOIC ACID
  • SMILES O=C(O)C#CCO

Description

4-Hydroxybut-2-ynoic acid features a conjugated alkyne-carboxylic acid motif paired with a terminal hydroxyl group, enabling direct incorporation into bioconjugation workflows. The electron-deficient alkyne facilitates efficient copper-catalyzed azide-alkyne cycloaddition, while the hydroxyl moiety offers a handle for derivatization or protection. This bifunctional scaffold supports modular synthesis in chemical biology and materials science applications.

Application

4-Hydroxybut-2-ynoic acid serves as a versatile building block in synthetic organic chemistry, enabling access to functionalized γ-lactones and conjugated systems via cyclization or further derivatization. Its terminal alkyne and hydroxyl groups offer orthogonal reactivity for copper-catalyzed coupling and selective protection strategies. The compound demonstrates good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in medicinal chemistry and natural product analog development.

Synthesis

  • Route1
    • null|null
      110-65-6
    • ~99%
    • In-stock
      4-Hydroxybut-2-ynoic acid|CS-0005249
      7218-52-2

    References

    • Matsumura, Shuichi; Yoda, Nobuo; Endo, Masato; Yoshikawa, Sadao Chemistry Letters, 1990 , # 4 p. 647 - 648
  • Route2
    • 4-((Tetrahydro-2H-pyran-2-yl)oxy)but-2-ynoic acid|CS-0371352
      116053-25-9
    • ~%
    • In-stock
      4-Hydroxybut-2-ynoic acid|CS-0005249
      7218-52-2

    References

    • Johnson, C. David; Lane, Simon; Edwards, Philip N.; Taylor, Peter J. Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 5130 - 5139
  • Route3
    • null|null
      4544-40-5
    • ~%
    • In-stock
      4-Hydroxybut-2-ynoic acid|CS-0005249
      7218-52-2

    References

    • Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), , vol. 21, p. 1706 - 1711 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, , vol. 21, # 8 p. 1763 - 1769

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   57.53
  • LogP   -0.9333
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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