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CS-W001157 4
Total: USD 88.00

methyl oxolane-3-carboxylate

  • CAS No. 53662-85-4

  • Cat. No. CS-W004271
  • Molecule weight130.14
  • Purity≥95%
  • MDL No.MFCD06203928

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

methyl oxolane-3-carboxylate|CS-W004271

Structure of 53662-85-4

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General Information

  • CAS No. 53662-85-4
  • Cat. No. CS-W004271
  • Purity ≥95%
  • MDL No. MFCD06203928
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₀O₃
  • Molecular Weight 130.14
  • Synonym(s) Methyl tetrahydro-3-furoate
  • SMILES COC(=O)C1COCC1

Description

Methyl tetrahydrofuran-3-carboxylate is a bench-stable, moisture-tolerant heterocyclic ester featuring a stereogenic center at the 3-position. This compound integrates readily into synthetic sequences requiring chiral building blocks, particularly in asymmetric synthesis and medicinal chemistry applications. Its constrained cyclic structure enhances conformational rigidity, improving selectivity in downstream transformations.

Application

Methyl tetrahydrofuran-3-carboxylate serves as a versatile building block in synthetic organic chemistry, offering a stable, bench-ready platform for the construction of heterocyclic scaffolds and bioactive molecules. Its functional group tolerance enables reliable participation in nucleophilic additions, cross-coupling reactions, and asymmetric transformations. The tetrahydrofuran ring provides conformational rigidity beneficial for stereocontrolled synthesis, while the ester moiety facilitates downstream derivatization. This compound functions effectively in both medicinal chemistry lead optimization and process-scale synthesis.

Synthesis

  • Route1
    • null|null
      865-33-8
    • In-stock
      (S)-(Tetrahydrofuran-3-yl)methanol|CS-0053251
      124391-75-9
    • ~82%
    • In-stock
      methyl oxolane-3-carboxylate|CS-W004271
      53662-85-4

    References

    • Powell, Adam B.; Stahl, Shannon S. Organic Letters, 2013 , vol. 15, # 19 p. 5072 - 5075
  • Route2
    • null|null
      67-56-1
    • In-stock
      Tetrahydrofuran-3-carboxylic acid|CS-W004096
      89364-31-8
    • ~87%
    • In-stock
      methyl oxolane-3-carboxylate|CS-W004271
      53662-85-4

    References

    • Solladie-Cavallo, Ariette; Roche, Didier; Fischer, Jean; De Cian, Andre Journal of Organic Chemistry, 1996 , vol. 61, # 8 p. 2690 - 2694
  • Route3
    • Methyl 4,5-dihydrofuran-3-carboxylate|CS-0497990
      53750-81-5
    • ~%
    • In-stock
      methyl oxolane-3-carboxylate|CS-W004271
      53662-85-4

    References

    • Boekelheide; Morrison Journal of the American Chemical Society, 1958 , vol. 80, p. 3905,3907

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   35.53
  • LogP   0.1959
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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