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CS-W001157 4
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2-Cyanoethyl acetoacetate

  • CAS No. 65193-87-5

  • Cat. No. CS-0088550
  • Purity≥95%
  • MDL No.MFCD24687999

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

2-Cyanoethyl acetoacetate|CS-0088550

Structure of 65193-87-5

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General Information

  • CAS No. 65193-87-5
  • Cat. No. CS-0088550
  • Purity ≥95%
  • MDL No. MFCD24687999
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO₃
  • Molecular Weight 155.15
  • Synonym(s) None
  • SMILES CC(CC(OCCC#N)=O)=O

Description

2-Cyanoethyl 3-oxobutanoate features a strategically positioned cyanoethyl ester and β-keto carbonyl group, enabling efficient Michael addition reactions. This bifunctional scaffold integrates readily into synthetic sequences requiring nucleophilic acylation or conjugate addition. The molecule exhibits robust stability under standard conditions, facilitating straightforward handling in organic synthesis workflows.

Application

2-Cyanoethyl 3-oxobutanoate serves as a versatile Michael acceptor and key building block in heterocyclic synthesis, enabling efficient access to substituted pyrrolidines and γ-lactams via tandem cyclization. Its α,β-unsaturated ester functionality reacts readily with nucleophiles under mild conditions, while the cyano and ketone groups provide orthogonal handles for further functionalization. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for scalable synthetic workflows in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Suarez, Margarita; De Armas, Merly; Ramirez, Oney; Alvarez, Amaury; Martinez-Alvarez, Roberto; Molero, Dolores; Seoane, Carlos; Liz, Ramon; De Armas, Hector Novoa; Blaton, Norbert M.; Peeters, Oswald M.; Martin, Nazario New Journal of Chemistry, 2005 , vol. 29, # 12 p. 1567 - 1576
  • Route2

    References

    • Gorlitzer; Baltrusch Pharmazie, 2000 , vol. 55, # 10 p. 747 - 750
  • Route3
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      674-82-8
    • In-stock
      3-hydroxypropanenitrile|CS-W001263
      109-78-4
    • ~%
    • In-stock
      2-Cyanoethyl acetoacetate|CS-0088550
      65193-87-5

    References

    • Sircar; Gregor; Anderson; Haleen; Shih; Weishaar; Steffen; Pugsley; Taylor Journal of Medicinal Chemistry, 1991 , vol. 34, # 7 p. 2248 - 2260

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   67.16
  • LogP   0.42238
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   4

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