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CS-W001157 4
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Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

  • CAS No. 20197-75-5

  • Cat. No. CS-0061853
  • Purity≥98%
  • MDL No.None

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

Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate|CS-0061853

Structure of 20197-75-5

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General Information

  • CAS No. 20197-75-5
  • Cat. No. CS-0061853
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀O₄
  • Molecular Weight 194.18
  • Synonym(s) Methyl 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate
  • SMILES COC(=O)C1=CC2=C(C=C1)OCCO2

Description

Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate features a rigid, electron-rich benzodioxole core paired with a pendant ester group, enabling seamless integration into complex molecular architectures. This bench-stable scaffold delivers enhanced solubility and metabolic stability in synthetic routes targeting bioactive compounds.

Application

Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to bioactive heterocyclic scaffolds. Its stable benzodioxole core exhibits favorable metabolic resistance and enhances solubility, while the ester functionality facilitates selective derivatization via hydrolysis or nucleophilic substitution. The compound functions reliably in standard coupling reactions and is compatible with diverse synthetic transformations, supporting robust workflow integration in API development and lead optimization.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      2,3-dihydro-1,4-benzodioxine-6-carboxylic acid|CS-W002623
      4442-54-0
    • ~81%
    • In-stock
      Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate|CS-0061853
      20197-75-5

    References

    • Lo Monte, Fabio; Kramer, Thomas; Gu, Jiamin; Brodrecht, Martin; Pilakowski, Johannes; Fuertes, Ana; Dominguez, Juan Manuel; Plotkin, Batya; Eldar-Finkelman, Hagit; Schmidt, Boris European Journal of Medicinal Chemistry, 2013 , vol. 61, p. 26 - 40
  • Route2
    • In-stock
      Methyl 3,4-dihydroxybenzoate|CS-Z0026
      2150-43-8
    • null|null
      106-93-4
    • ~13%
    • In-stock
      Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate|CS-0061853
      20197-75-5

    References

    • PRESIDENT AND FELLOWS OF HARVARD COLLEGE Patent: WO2009/151561 A2, 2009 ; Location in patent: Page/Page column 68 ;
  • Route3
    • null|null
      54110-86-0
    • ~67%
    • In-stock
      Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate|CS-0061853
      20197-75-5

    References

    • Toracca, Karen E.; Kuwabe, Shin-Itsu; Buchwald, Stephen L. Journal of the American Chemical Society, 2000 , vol. 122, # 51 p. 12907 - 12908

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   44.76
  • LogP   1.2444
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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