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CS-W001157 4
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Carbethoxymethyl cyclopropyl ketone

  • CAS No. 24922-02-9

  • Cat. No. CS-W009178
  • Purity≥96%
  • MDL No.MFCD00184570

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

Carbethoxymethyl cyclopropyl ketone|CS-W009178

Structure of 24922-02-9

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General Information

  • CAS No. 24922-02-9
  • Cat. No. CS-W009178
  • Purity ≥96%
  • MDL No. MFCD00184570
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂O₃
  • Molecular Weight 156.18
  • Synonym(s) Ethyl 3-cyclopropyl-3-oxopropanoate; Ethyl 3-cyclopropyl-3-oxopropionate; Ethyl β-cyclopropyl-β-ketopropionate; NSC 97121; β-Oxocyclopropanepropanoic acid ethyl ester
  • SMILES O=C(CC(OCC)=O)C1CC1

Description

Carbethoxymethyl cyclopropyl ketone features a strained cyclopropyl ring fused to a ketone bearing a carbethoxy-methyl side chain. This arrangement imparts high reactivity for cycloaddition and nucleophilic functionalization, enabling efficient construction of complex heterocycles under mild conditions. The molecule exhibits excellent stability during storage and compatibility with common organic solvents.

Application

Carbethoxymethyl cyclopropyl ketone serves as a versatile synthon in heterocyclic synthesis, enabling efficient construction of substituted pyrrolidines and γ-lactams via Michael addition or cyclization cascades. Its cyclopropyl moiety imparts conformational rigidity, while the ester and ketone functionalities offer orthogonal reactivity for sequential transformations. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and scalable process development.

Synthesis

  • Route1
    • In-stock
      3-Ethoxy-3-oxopropanoic acid potassium|CS-D1444
      6148-64-7
    • null|null
      4023-34-1
    • ~93%
    • In-stock
      Carbethoxymethyl cyclopropyl ketone|CS-W009178
      24922-02-9

    References

    • DAIICHI PHARMACEUTICAL CO., LTD. Patent: EP1479681 A1, 2004 ; Location in patent: Page 59 ;
  • Route2
    • null|null
      765-43-5
    • ~54%
    • 2-Fluoro-1-phenylethanone|CS-0037091
      450-95-3
    • In-stock
      Carbethoxymethyl cyclopropyl ketone|CS-W009178
      24922-02-9

    References

    • E. R. Squibb and Sons, Inc. Patent: US5506219 A1, 1996 ; US 5506219 A
  • Route3
    • In-stock
      3-Ethoxy-3-oxopropanoic acid|CS-0016016
      1071-46-1
    • null|null
      4023-34-1
    • ~64%
    • In-stock
      Carbethoxymethyl cyclopropyl ketone|CS-W009178
      24922-02-9

    References

    • J. Uriach and Cia, S.A. Patent: US5827863 A1, 1998 ; US 5827863 A

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   0.9187
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   4

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