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CS-W001157 4
Total: USD 88.00

4-(Benzyloxy)-4-oxobutanoic acid

  • CAS No. 103-40-2

  • Cat. No. CS-W002611
  • Purity≥97%
  • MDL No.MFCD00447717

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

4-(Benzyloxy)-4-oxobutanoic acid|CS-W002611

Structure of 103-40-2

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General Information

  • CAS No. 103-40-2
  • Cat. No. CS-W002611
  • Purity ≥97%
  • MDL No. MFCD00447717
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂O₄
  • Molecular Weight 208.21
  • Synonym(s) None
  • SMILES O=C(O)CCC(=O)OCC=1C=CC=CC1

Description

4-(Benzyloxy)-4-oxobutanoic acid features a benzyl ether-linked β-keto acid scaffold, enabling direct incorporation into synthetic sequences requiring stable, functionalized acyl precursors. The benzyloxy group provides orthogonal protection for hydroxyl functionalities during multistep transformations. This compound serves as a key intermediate in the synthesis of bioactive esters and lactones.

Application

4-(Benzyloxy)-4-oxobutanoic acid serves as a versatile building block for heterocyclic synthesis, particularly in the construction of γ-lactones and substituted pyrones. Its α,β-unsaturated ketone functionality enables Michael additions and aldol condensations under mild conditions. The benzyloxy group provides orthogonal protection for alcohols, facilitating sequential transformations. This compound exhibits good bench stability and is amenable to standard purification methods, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Krishnan, K. Syam; Bengtsson, Christoffer; Good, James A. D.; Mirkhanov, Shamil; Chorell, Erik; Johansson, Lennart B.-A.; Almqvist, Fredrik Journal of Organic Chemistry, 2013 , vol. 78, # 23 p. 12207 - 12213
  • Route2
    • null|null
      15026-16-1
    • ~91%
    • In-stock
      4-(Benzyloxy)-4-oxobutanoic acid|CS-W002611
      103-40-2

    References

    • Yadav; Reddy, B. V. Subba; Rao, K. Sanjeeva; Harikishan Synlett, 2002 , # 5 p. 826 - 828
  • Route3
    • In-stock
      Succinic anhydride|CS-0011581
      108-30-5
    • null|null
      121-44-8
    • ~85%
    • In-stock
      4-(Benzyloxy)-4-oxobutanoic acid|CS-W002611
      103-40-2

    References

    • NeoRx Corporation Patent: US5112953 A1, 1992 ;

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   63.6
  • LogP   1.5946
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   5

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