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CS-W001157 4
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(E)-Ethyl 2-cyano-3-ethoxyacrylate

  • CAS No. 42466-67-1

  • Cat. No. CS-0023511
  • Purity≥97%
  • MDL No.MFCD00009136

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

(E)-Ethyl 2-cyano-3-ethoxyacrylate|CS-0023511

Structure of 42466-67-1

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General Information

  • CAS No. 42466-67-1
  • Cat. No. CS-0023511
  • Purity ≥97%
  • MDL No. MFCD00009136
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁NO₃
  • Molecular Weight 169.18
  • Synonym(s) ethyl (E)-2-cyano-3-ethoxyacrylate
  • SMILES O=C(OCC)/C(C#N)=C/OCC

Description

(E)-Ethyl 2-cyano-3-ethoxyacrylate is a bench-stable, electron-deficient acrylate ester featuring a conjugated cyano and ethoxy group. This configuration enables efficient Michael addition reactions and Diels-Alder cycloadditions under mild conditions. The (E)-geometry ensures predictable stereochemistry in synthetic transformations. It serves as a key building block for heterocyclic compounds and functionalized polymers.

Application

(E)-Ethyl 2-cyano-3-ethoxyacrylate serves as a versatile Michael acceptor and key building block in heterocyclic synthesis, enabling efficient access to pyrroles, pyridines, and other nitrogen-containing scaffolds via condensation and cycloaddition reactions. Its well-defined (E)-configuration ensures predictable stereochemical outcomes, while the cyano and ester groups offer orthogonal reactivity for sequential transformations. Bench-stable and readily purified by flash chromatography, it functions effectively in multistep syntheses requiring high functional group tolerance and reproducible yields.

Synthesis

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    • In-stock
      (E)-Ethyl 2-cyano-3-ethoxyacrylate|CS-0023511
      42466-67-1

    References

    • Jones Journal of the American Chemical Society, 1952 , vol. 74, p. 4889

Safety Information

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GHS Pictogram :
GHS No : GHS05,GHS07,GHS08
Signal Word : Danger
UN#: 3335
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H318-H334-H335
Precautionary Statements : P261-P264-P270-P271-P272-P280-P285-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   59.32
  • LogP   1.62958
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   4

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