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CS-W001157 4
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Methyl 5-oxotetrahydrofuran-2-carboxylate

  • CAS No. 3885-29-8

  • Cat. No. CS-0435430
  • Purity≥98%
  • MDL No.None

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

Methyl 5-oxotetrahydrofuran-2-carboxylate|CS-0435430

Structure of 3885-29-8

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General Information

  • CAS No. 3885-29-8
  • Cat. No. CS-0435430
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈O₄
  • Molecular Weight 144.13
  • Synonym(s) methyl5-oxooxolane-2-carboxylate
  • SMILES O=C(C(CC1)OC1=O)OC

Description

Methyl 5-oxotetrahydrofuran-2-carboxylate features a reactive α,β-unsaturated carbonyl system within a saturated heterocyclic framework, enabling efficient conjugate additions and cycloadditions. The ester functionality enhances solubility in polar organic solvents while maintaining stability under standard bench conditions. This scaffold serves as a key building block in the synthesis of bioactive heterocycles and natural product analogs.

Application

Methyl 5-oxotetrahydrofuran-2-carboxylate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to oxygenated carbocyclic and heterocyclic scaffolds. Its α,β-unsaturated γ-lactone functionality facilitates nucleophilic addition and cycloaddition reactions, while the ester group supports subsequent transformations such as reduction or hydrolysis. Bench-stable and readily purified by distillation or chromatography, it functions effectively in multi-step sequences requiring functional group compatibility and predictable reactivity.

Synthesis

  • Route1

    References

    • Drioli, Sara; Nitti, Patrizia; Pitacco, Giuliana; Tossut, Laura; Valentin, Ennio Tetrahedron Asymmetry, 1999 , vol. 10, # 14 p. 2713 - 2728
  • Route2

    References

    • Drioli, Sara; Nitti, Patrizia; Pitacco, Giuliana; Tossut, Laura; Valentin, Ennio Tetrahedron Asymmetry, 1999 , vol. 10, # 14 p. 2713 - 2728
  • Route3

    References

    • Utaka, Masanori; Nakatano, Manabu; Takeda, Akira Journal of Organic Chemistry, 1986 , vol. 51, # 7 p. 1140 - 1141

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   -0.135
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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