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CS-W001157 4
Total: USD 88.00

3-Bromofuran-2,5-dione

  • CAS No. 5926-51-2

  • Cat. No. CS-W021883
  • Purity≥95%
  • MDL No.MFCD00005519

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

3-Bromofuran-2,5-dione|CS-W021883

Structure of 5926-51-2

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General Information

  • CAS No. 5926-51-2
  • Cat. No. CS-W021883
  • Purity ≥95%
  • MDL No. MFCD00005519
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄HBrO₃
  • Molecular Weight 176.95
  • Synonym(s) Bromomaleic anhydride
  • SMILES O=C(C(Br)=C1)OC1=O

Description

3-Bromofuran-2,5-dione is a brominated furanone featuring electron-deficient double bonds and reactive carbonyl groups. This compound serves as a potent Michael acceptor in conjugate addition reactions and integrates readily into heterocyclic scaffolds under mild conditions. Its stability enables reliable use in synthetic sequences requiring controlled electrophilic engagement.

Application

3-Bromofuran-2,5-dione serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the 3-position via palladium-catalyzed cross-coupling reactions. Its electron-deficient furan scaffold exhibits high reactivity in nucleophilic substitution and cycloaddition processes, facilitating access to substituted heterocycles. The molecule demonstrates excellent bench stability and compatibility with common protecting groups, making it well-suited for multi-step synthesis and process-scale applications.

Synthesis

  • Route1
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      101349-74-0
    • ~%
    • In-stock
      3-Bromofuran-2,5-dione|CS-W021883
      5926-51-2

    References

    • Justus Liebigs Annalen der Chemie, , vol. 280, p. 209
  • Route2
    • 2-Bromobut-2-enedioic acid|CS-0343894
      584-99-6
    • ~%
    • In-stock
      3-Bromofuran-2,5-dione|CS-W021883
      5926-51-2

    References

    • Justus Liebigs Annalen der Chemie, , vol. Suppl.1, p. 368
  • Route3
    • null|null
      108-31-6
    • ~%
    • In-stock
      3-Bromofuran-2,5-dione|CS-W021883
      5926-51-2

    References

    • Zhurnal Obshchei Khimii, , vol. 24, p. 1216,1219; engl. Ausg. S. 1205, 1206

Safety Information

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

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   0.3486
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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