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CS-W001157 4
Total: USD 88.00

7-Bromo-2,3-dioxoindoline

  • CAS No. 20780-74-9

  • Cat. No. CS-W002675
  • Molecule weight226.03
  • Purity≥97%
  • MDL No.MFCD00774354

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

7-Bromo-2,3-dioxoindoline|CS-W002675

Structure of 20780-74-9

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General Information

  • CAS No. 20780-74-9
  • Cat. No. CS-W002675
  • Purity ≥97%
  • MDL No. MFCD00774354
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄BrNO₂
  • Molecular Weight 226.03
  • Synonym(s) 7-Bromoisatin; 7-Bromo-2,3-dioxoindoline
  • SMILES BrC1=CC=CC(C2=O)=C1NC2=O

Description

7-Bromo-2,3-dioxoindoline features a brominated indoline core with two carbonyl groups at the 2 and 3 positions, delivering enhanced reactivity for cross-coupling and heterocycle formation. This bench-stable, moisture-tolerant scaffold integrates readily into complex molecular architectures, enabling efficient access to bioactive indole derivatives in medicinal chemistry and materials science applications.

Application

7-Bromo-2,3-dioxoindoline serves as a versatile building block for the synthesis of biologically active heterocycles, particularly in medicinal chemistry and natural product derivatization. Its bromine substituent enables facile palladium-catalyzed cross-coupling reactions, while the ortho-dicarbonyl framework facilitates enolization and condensation processes. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for iterative synthetic workflows and scaffold diversification.

Synthesis

  • Route1
    • N-(2-bromophenyl)-2-(hydroxyimino)acetamide|CS-0339946
      101080-38-0
    • ~92%
    • In-stock
      7-Bromo-2,3-dioxoindoline|CS-W002675
      20780-74-9

    References

    • ENDO PHARMACEUTICALS INC.; SMITH, Roger, Astbury; THOMPSON, Scott, Kevin; HOSAHALLI, Subramanya; BEJUGAM, Mallesham; NANDURI, Srinivas; PANIGRAHI, Sunil, Kumar; MAHALINGAM, Natarajan Patent: WO2012/58671 A1, 2012 ; Location in patent: Page/Page column 106 ;
  • Route2
    • null|null
      320734-34-7
    • ~9%
    • In-stock
      7-Bromo-2,3-dioxoindoline|CS-W002675
      20780-74-9
    • null|null
      320734-37-0

    References

    • Tetrahedron Letters, , vol. 41, # 47 p. 9089 - 9093
  • Route3
    • null|null
      615-36-1
    • ~%
    • In-stock
      7-Bromo-2,3-dioxoindoline|CS-W002675
      20780-74-9

    References

    • Journal of Medicinal Chemistry, , vol. 50, # 1 p. 21 - 39

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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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