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Ethyl (E)-4,4-dimethoxybut-2-enoate

  • CAS No. 114736-25-3

  • Cat. No. CS-0141403
  • Purity≥98%
  • MDL No.MFCD06204472

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

Ethyl (E)-4,4-dimethoxybut-2-enoate|CS-0141403

Structure of 114736-25-3

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General Information

  • CAS No. 114736-25-3
  • Cat. No. CS-0141403
  • Purity ≥98%
  • MDL No. MFCD06204472
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄O₄
  • Molecular Weight 174.19
  • Synonym(s) (E)-Ethyl 4,4-dimethoxybut-2-enoate
  • SMILES O=C(OCC)/C=C/C(OC)OC

Description

Ethyl (E)-4,4-dimethoxybut-2-enoate features a conjugated enoate system with dual methoxy groups at the gamma position, enhancing electron density and stabilizing the E-configuration. This stereochemically defined intermediate integrates readily into Michael additions and Diels-Alder reactions, offering high reactivity under mild conditions. The ethyl ester moiety enables straightforward functionalization, while the dimethoxy substitution improves solubility in polar organic solvents.

Application

Ethyl (E)-4,4-dimethoxybut-2-enoate serves as a versatile synthon in synthetic organic chemistry, enabling efficient access to substituted dihydropyran and tetrahydropyran ring systems. Its conjugated enoate functionality facilitates Michael additions and Diels–Alder reactions, while the geminal dimethoxy group supports controlled hydrolysis and subsequent functionalization. The compound exhibits excellent bench stability and is readily purified by distillation or flash chromatography, making it well-suited for iterative synthesis workflows in medicinal chemistry and natural product development.

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   0.7246
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   5

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