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CS-W001157 4
Total: USD 88.00

4-Bromo-1H-indole-2,3-dione

  • CAS No. 20780-72-7

  • Cat. No. CS-W008631
  • Purity≥98%
  • MDL No.MFCD03618555

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

4-Bromo-1H-indole-2,3-dione|CS-W008631

Structure of 20780-72-7

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General Information

  • CAS No. 20780-72-7
  • Cat. No. CS-W008631
  • Purity ≥98%
  • MDL No. MFCD03618555
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄BrNO₂
  • Molecular Weight 226.03
  • Synonym(s) 4-Bromoindole-2,3-dione; 4-Bromoindoline-2,3-dione; 4-Bromoisatin; 4-Bromo-2,3-indolinedione
  • SMILES O=C1NC2=C(C(Br)=CC=C2)C1=O

Description

4-Bromo-1H-indole-2,3-dione features a brominated indole core with two carbonyl groups, offering enhanced electrophilicity and stability under standard conditions. This electron-deficient scaffold integrates readily into heterocyclic systems, enabling efficient coupling in transition-metal-catalyzed reactions. The para-bromine facilitates direct functionalization, streamlining access to complex molecular architectures.

Application

4-Bromo-1H-indole-2,3-dione serves as a versatile building block in heterocyclic synthesis, enabling efficient access to functionalized indole derivatives through palladium-catalyzed cross-coupling reactions. Its brominated position facilitates direct substitution under standard Suzuki, Stille, or Negishi conditions, while the quinone functionality supports electrophilic transformations and Diels-Alder cycloadditions. The compound exhibits excellent bench stability and simplifies purification due to its crystalline nature, making it well-suited for iterative synthesis workflows in medicinal chemistry and materials science.

Synthesis

  • Route1
    • (E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide|CS-0555200
      65971-74-6
    • ~0%
    • In-stock
      6-Bromoisatin|CS-W002793
      6326-79-0
    • In-stock
      4-Bromo-1H-indole-2,3-dione|CS-W008631
      20780-72-7

    References

    • WO2006/44415 A2, ; Page/Page column 118 ; WO 2006/044415 A2
  • Route2
    • null|null
      302-17-0
    • null|null
      591-19-5
    • ~39%
    • In-stock
      4-Bromo-1H-indole-2,3-dione|CS-W008631
      20780-72-7

    References

    • Chinese Chemical Letters, , vol. 24, # 10 p. 929 - 933
  • Route3
    • (E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide|CS-0555200
      65971-74-6
    • ~%
    • In-stock
      4-Bromo-1H-indole-2,3-dione|CS-W008631
      20780-72-7

    References

    • European Journal of Pharmacology, , vol. 556, # 1-3 p. 200 - 206

Safety Information

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GHS Pictogram : N/A
GHS No : N/A
Signal Word : N/A
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

  • TPSA   46.17
  • LogP   1.5839
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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