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CS-W001157 4
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5-Methoxyisobenzofuran-1,3-dione

  • CAS No. 28281-76-7

  • Cat. No. CS-W019718
  • Purity≥98%
  • MDL No.MFCD02670942

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

5-Methoxyisobenzofuran-1,3-dione|CS-W019718

Structure of 28281-76-7

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General Information

  • CAS No. 28281-76-7
  • Cat. No. CS-W019718
  • Purity ≥98%
  • MDL No. MFCD02670942
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆O₄
  • Molecular Weight 178.14
  • Synonym(s) METHYL N-(DIPHENYLMETHYLENE)-L-SERINATE
  • SMILES O=C1OC(C2=C1C=CC(OC)=C2)=O

Description

5-Methoxyisobenzofuran-1,3-dione features a fused bicyclic core with electron-withdrawing carbonyl groups and a methoxy substituent at the 5-position. This configuration imparts enhanced stability and modulates reactivity in Diels-Alder cycloadditions. The compound serves as a valuable dienophile in synthetic routes to complex heterocycles and natural product analogs.

Application

5-Methoxyisobenzofuran-1,3-dione serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzofuran derivatives. Its electron-deficient quinone core facilitates Diels-Alder reactions and nucleophilic additions, while the methoxy group enhances solubility and modulates reactivity. Bench-stable and readily purified by recrystallization, it functions reliably in multistep syntheses involving heterocyclic scaffolds and natural product analogs.

Synthesis

  • Route1

    References

    • ASTEX THERAPEUTICS LIMITED Patent: WO2008/44045 A1, 2008 ; Location in patent: Page/Page column 277-278 ; WO 2008/044045 A1
  • Route2

    References

    • Prichard Journal of the American Chemical Society, 1956 , vol. 78, p. 6137
  • Route3
    • 6-Methoxyisobenzofuran-1(3H)-one|CS-0332108
      4741-63-3
    • ~90%
    • In-stock
      5-Methoxyisobenzofuran-1,3-dione|CS-W019718
      28281-76-7

    References

    • Leblois, Danielle; Piessard, Sylvie; Baut, Guillaume Le; Kumar, Piyush; Brion, Jean-Daniel; et al. European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 229 - 238

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
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

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   1.0058
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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