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(E)-Methyl 2-((dimethylamino)methylene)-3-oxobutanoate

  • CAS No. 203186-56-5

  • Cat. No. CS-0155159
  • Purity≥97%
  • MDL No.MFCD08689663

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

(E)-Methyl 2-((dimethylamino)methylene)-3-oxobutanoate|CS-0155159

Structure of 203186-56-5

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General Information

  • CAS No. 203186-56-5
  • Cat. No. CS-0155159
  • Purity ≥97%
  • MDL No. MFCD08689663
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₃NO₃
  • Molecular Weight 171.19
  • Synonym(s) Methyl 2-acetyl-3-(dimethylamino)acrylate
  • SMILES CC(=O)/C(=C\N(C)C)/C(=O)OC

Description

(E)-Methyl 2-((dimethylamino)methylene)-3-oxobutanoate is a bench-stable enolizable β-keto ester featuring an electron-rich exocyclic double bond. This conjugated system enables efficient Michael additions and Diels-Alder reactions, integrating readily into complex molecular architectures. The dimethylamino group enhances nucleophilicity at the α-carbon, facilitating regioselective transformations under mild conditions.

Application

(E)-Methyl 2-((dimethylamino)methylene)-3-oxobutanoate serves as a versatile enolizable building block in synthetic organic chemistry, enabling efficient access to substituted pyrroles and other heterocyclic scaffolds via condensation reactions. Its conjugated enone system facilitates Michael additions and [4+2] cycloadditions, while the dimethylamino group enhances electrophilicity at the β-carbon. Bench-stable and readily purified by distillation or chromatography, it functions effectively in multi-step syntheses requiring functional group compatibility and predictable reactivity.

Synthesis

  • Route1

    References

    • Tetrahedron Letters, , vol. 41, # 44 p. 8609 - 8613

Safety Information

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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   46.61
  • LogP   0.1939
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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