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CS-W001157 4
Total: USD 88.00

Benzyl acetoacetate

  • CAS No. 5396-89-4

  • Cat. No. CS-0071955
  • Purity≥97%
  • MDL No.MFCD00008785

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

Benzyl acetoacetate|CS-0071955

Structure of 5396-89-4

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General Information

  • CAS No. 5396-89-4
  • Cat. No. CS-0071955
  • Purity ≥97%
  • MDL No. MFCD00008785
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂O₃
  • Molecular Weight None
  • Synonym(s) Benzyl-2-oxobutanoate; Benzyl acetoacetate
  • SMILES O=C(OCC1=CC=CC=C1)CC(C)=O

Description

Benzyl acetoacetate serves as a key synthetic intermediate featuring a reactive β-keto ester moiety flanked by a benzyl group. This combination enables efficient Michael additions, Claisen condensations, and heterocycle formations under mild conditions. The benzyl protection enhances stability during storage and reaction handling, while the enolizable carbonyl system supports diverse transformations in medicinal chemistry and natural product synthesis.

Application

Benzyl acetoacetate serves as a versatile synthon in organic synthesis, enabling efficient construction of substituted pyranones and heterocyclic scaffolds via Claisen condensation and Michael addition protocols. Its benzyl ester functionality provides enhanced bench stability and facilitates straightforward purification, while the β-ketoester motif exhibits predictable reactivity in standard coupling and cyclization reactions. Widely employed in medicinal chemistry and natural product synthesis, it functions as a key building block for bioactive molecule assembly.

Synthesis

  • Route1
    • Benzyl acetate Benzyl Alcohol  Impurity|CS-0228843
      140-11-4
    • ~76%
    • In-stock
      Benzyl acetoacetate|CS-0071955
      5396-89-4

    References

    • Yoshizawa, Kazuhiro; Toyota, Shinji; Toda, Fumio Tetrahedron Letters, 2001 , vol. 42, # 45 p. 7983 - 7985
  • Route2
    • null|null
      2343-88-6
    • In-stock
      Benzyl alcohol|CS-4355
      100-51-6
    • ~%
    • In-stock
      Benzyl acetoacetate|CS-0071955
      5396-89-4

    References

    • Journal of Organic Chemistry, , vol. 26, p. 225 - 227
  • Route3
    • null|null
      72324-39-1
    • In-stock
      Benzyl alcohol|CS-4355
      100-51-6
    • ~93%
    • In-stock
      Benzyl acetoacetate|CS-0071955
      5396-89-4

    References

    • More; Mahulikar Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006 , vol. 45, # 3 p. 823 - 825

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   43.37
  • LogP   1.7089
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   4

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