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Ethyl 1-cyanocyclobutane-1-carboxylate

  • CAS No. 28246-87-9

  • Cat. No. CS-0008648
  • Purity≥95%
  • MDL No.MFCD04114273

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

Ethyl 1-cyanocyclobutane-1-carboxylate|CS-0008648

Structure of 28246-87-9

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General Information

  • CAS No. 28246-87-9
  • Cat. No. CS-0008648
  • Purity ≥95%
  • MDL No. MFCD04114273
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁NO₂
  • Molecular Weight 153.18
  • Synonym(s) Ethyl 1-cyanocyclobutanecarboxylate
  • SMILES O=C(C1(C#N)CCC1)OCC

Description

Ethyl 1-cyanocyclobutane-1-carboxylate features a strained cyclobutane ring bearing both a cyano and ester group, enabling direct functionalization at the ring junction. This configuration facilitates C–C bond formation in synthetic sequences requiring constrained scaffolds. The molecule exhibits stability under standard conditions and integrates readily into complex molecular architectures.

Application

Ethyl 1-cyanocyclobutane-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to cyclobutane-containing scaffolds. The molecule combines a stable ester functionality with a pendant nitrile group, allowing for sequential transformations including hydrolysis, reduction, and nucleophilic addition. Its bench-stable nature and compatibility with diverse reaction conditions facilitate straightforward purification and integration into multi-step syntheses of biologically relevant heterocycles and medicinal intermediates.

Synthesis

  • Route1
    • null|null
      105-56-6
    • In-stock
      1,3-Dibromopropane|CS-W020641
      109-64-8
    • ~72%
    • In-stock
      Ethyl 1-cyanocyclobutane-1-carboxylate|CS-0008648
      28246-87-9

    References

    • TAKEDA PHARMACEUTICAL COMPANY LIMITED Patent: WO2009/67547 A1, 2009 ; Location in patent: Page/Page column 281-282 ; WO 2009/067547 A1
  • Route2
    • null|null
      2999-46-4
    • In-stock
      1,3-Dibromopropane|CS-W020641
      109-64-8
    • ~46%
    • In-stock
      Ethyl 1-cyanocyclobutane-1-carboxylate|CS-0008648
      28246-87-9

    References

    • Kalvin, Douglas; Ramalingam, Kondareddiar; Woodward, Ronald Synthetic Communications, 1985 , vol. 15, # 4 p. 267 - 272
  • Route3
    • null|null
      105-56-6
    • ~%
    • In-stock
      Ethyl 1-cyanocyclobutane-1-carboxylate|CS-0008648
      28246-87-9

    References

    • Gosselck,J.; Winkler,A. Tetrahedron Letters, 1970 , p. 2437 - 2440

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   50.09
  • LogP   1.24338
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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