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CS-W001157 4
Total: USD 88.00

3-(Benzyloxy)cyclobutanecarboxylic acid

  • CAS No. 4958-02-5

  • Cat. No. CS-W008932
  • Purity≥95%
  • MDL No.MFCD00512751

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

3-(Benzyloxy)cyclobutanecarboxylic acid|CS-W008932

Structure of 4958-02-5

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General Information

  • CAS No. 4958-02-5
  • Cat. No. CS-W008932
  • Purity ≥95%
  • MDL No. MFCD00512751
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄O₃
  • Molecular Weight 206.24
  • Synonym(s) Cyclobutanecarboxylic acid, 3-(phenylmethoxy)-Cyclobutanecarboxylic acid, 3-(benzyloxy)-(6CI,7CI,8CI)
  • SMILES O=C(O)C(C1)CC1OCC2=CC=CC=C2

Description

This cyclobutanecarboxylic acid derivative features a benzyloxy substituent at the 3-position, delivering enhanced solubility and stability in organic media. The aromatic ether moiety facilitates integration into bioactive scaffolds, while the carboxylic acid group enables direct coupling or derivatization under standard conditions.

Application

3-(Benzyloxy)cyclobutanecarboxylic acid serves as a versatile building block for medicinal chemistry and natural product synthesis, enabling the introduction of a rigid cyclobutane scaffold with orthogonal benzyloxy and carboxylic acid functionalities. The molecule exhibits excellent bench stability, facilitates straightforward derivatization via esterification or amide coupling, and supports diverse downstream transformations including hydrogenolysis to release the free alcohol. Its defined stereochemistry and compatibility with standard purification methods make it a practical choice for high-throughput screening campaigns and process-scale applications.

Synthesis

  • Route1
    • 3-(Phenylmethoxy)-1,1-cyclobutanedicarboxylic acid|CS-0054585
      84182-46-7
    • ~92%
    • In-stock
      3-(Benzyloxy)cyclobutanecarboxylic acid|CS-W008932
      4958-02-5

    References

    • AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa Patent: WO2011/143366 A1, 2011 ; Location in patent: Page/Page column 44 ; WO 2011/143366 A1
  • Route2
    • Diisopropyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate|CS-0052774
      869109-30-8
    • ~%
    • In-stock
      3-(Benzyloxy)cyclobutanecarboxylic acid|CS-W008932
      4958-02-5

    References

    • EP1748048 A1, ; Page/Page column 56 ;
  • Route3
    • Diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate|CS-0052770
      54166-15-3
    • ~%
    • In-stock
      3-(Benzyloxy)cyclobutanecarboxylic acid|CS-W008932
      4958-02-5

    References

    • Helvetica Chimica Acta, , vol. 75, # 2 p. 589 - 603

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   46.53
  • LogP   2.0664
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   4

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