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CS-W001157 4
Total: USD 88.00

Ethyl 3-ethoxy-2-cyanoacrylate

  • CAS No. 94-05-3

  • Cat. No. CS-D1211
  • Purity≥96%
  • MDL No.None

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

Ethyl 3-ethoxy-2-cyanoacrylate|CS-D1211

Structure of 94-05-3

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General Information

  • CAS No. 94-05-3
  • Cat. No. CS-D1211
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁NO₃
  • Molecular Weight 169.18
  • Synonym(s) Acrylic acid, 2-cyano-3-ethoxy-, ethyl ester (6CI,7CI,8CI); 2-(Ethoxymethylene)-2-cyanoacetic acid ethyl ester; 2-Cyano-3-ethoxy-2-propenoic acid ethyl ester; Ethyl ethoxymethylenecyanoacetate
  • SMILES O=C(OCC)/C(C#N)=C/OCC

Description

Ethyl 3-ethoxy-2-cyanoacrylate is a bench-stable, moisture-tolerant acrylate ester featuring a cyano group at the α-position. This electron-deficient vinyl system enables efficient Michael additions and copolymerization reactions under mild conditions. The ethoxy substituent enhances solubility in organic solvents and supports controlled reactivity in synthetic workflows.

Application

Ethyl 3-ethoxy-2-cyanoacrylate serves as a versatile Michael acceptor and Diels-Alder dienophile, enabling efficient construction of substituted pyrrolidines and cyclohexenes. Its electrophilic β-carbon is readily attacked by nucleophiles under mild conditions, offering high functional group tolerance and facile purification due to its crystalline nature. The ethoxy and cyano groups enhance reactivity while maintaining bench stability, making it ideal for multi-step synthesis workflows in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      122-51-0
    • null|null
      105-56-6
    • ~83%
    • In-stock
      Ethyl 3-ethoxy-2-cyanoacrylate|CS-D1211
      94-05-3

    References

    • Chen, Li; Chen, Shaoqing; Michoud, Christophe Patent: US2006/4046 A1, 2006 ; Location in patent: Page/Page column 35 ; US 20060004046 A1
  • Route2
    • null|null
      122-51-0
    • ~%
    • In-stock
      Ethyl 3-ethoxy-2-cyanoacrylate|CS-D1211
      94-05-3

    References

    • Journal of the American Chemical Society, , vol. 69, p. 2234

Safety Information

Download SDS
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

Quality Control

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Computational Chemistry Data

  • TPSA   59.32
  • LogP   0.99348
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   4

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