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CS-W001157 4
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Ethyl 2-(ethoxymethylene)-3-oxobutyrate

  • CAS No. 3788-94-1

  • Cat. No. CS-M2053
  • Purity≥95%
  • MDL No.MFCD06797311

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

Ethyl 2-(ethoxymethylene)-3-oxobutyrate|CS-M2053

Structure of 3788-94-1

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General Information

  • CAS No. 3788-94-1
  • Cat. No. CS-M2053
  • Purity ≥95%
  • MDL No. MFCD06797311
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₄O₄
  • Molecular Weight 186.21
  • Synonym(s) Acetoacetic acid, 2-(ethoxymethylene)-, ethyl ester; ethyl 2-(ethoxymethylidene)-3-oxobutanoate
  • SMILES CC(/C(C(OCC)=O)=C\OCC)=O

Description

Ethyl 2-(ethoxymethylene)-3-oxobutyrate is a versatile β-keto ester derivative featuring a conjugated enol ether system. This structure enables efficient Michael additions and Claisen condensations under mild conditions, delivering complex carbonyl architectures with high regiocontrol. The ethoxymethylene group enhances reactivity while maintaining bench-stable handling characteristics.

Application

Ethyl 2-(ethoxymethylene)-3-oxobutyrate serves as a versatile β-keto ester building block in synthetic organic chemistry, enabling efficient construction of substituted pyran and furan heterocycles. Its well-defined reactivity facilitates aldol-type condensations and Michael additions, while the ethoxymethylene group supports facile functionalization via Knoevenagel or Claisen-type reactions. Bench-stable and amenable to straightforward purification, it functions reliably in multi-step syntheses requiring controlled carbon-carbon bond formation.

Synthesis

  • Route1
    • In-stock
      Ethyl acetoacetate|CS-0016216
      141-97-9
    • null|null
      122-51-0
    • ~80%
    • In-stock
      Ethyl 2-(ethoxymethylene)-3-oxobutyrate|CS-M2053
      3788-94-1

    References

    • TAKEDA PHARMACEUTICAL COMPANY LIMITED; POONI, Parminder, Kaur; MERCHANT, Kevin, John; KERR, Catrina, Morvern; HARRISON, David Patent: WO2011/83316 A1, 2011 ; Location in patent: Page/Page column 52-53 ; WO 2011/083316 A1
  • Route2
    • In-stock
      Ethyl acetoacetate|CS-0016216
      141-97-9
    • null|null
      149-73-5
    • ~72%
    • In-stock
      Ethyl 2-(ethoxymethylene)-3-oxobutyrate|CS-M2053
      3788-94-1

    References

    • Kivrakidou, Olga; Braese, Stefan; Huelshorst, Frank; Griebenow, Nils Organic Letters, 2004 , vol. 6, # 7 p. 1143 - 1146
  • Route3
    • null|null
      75-03-6
    • ~%
    • In-stock
      Ethyl 2-(ethoxymethylene)-3-oxobutyrate|CS-M2053
      3788-94-1

    References

    • Claisen Justus Liebigs Annalen der Chemie, 1897 , vol. 297, p. 57 Chemische Berichte, 1893 , vol. 26, p. 2731

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   52.6
  • LogP   1.0589
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   5

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