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CS-W001157 4
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5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one

  • CAS No. 90725-49-8

  • Cat. No. CS-0036961
  • Purity≥98%
  • MDL No.None

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

5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0036961

Structure of 90725-49-8

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General Information

  • CAS No. 90725-49-8
  • Cat. No. CS-0036961
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈BrNO
  • Molecular Weight 226.07
  • Synonym(s) 5-Bromo-3-methylindolin-2-one
  • SMILES CC1C2=CC(=CC=C2NC1=O)Br

Description

5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one is a bench-stable heterocyclic ketone featuring a brominated indolinone core. This electron-deficient scaffold integrates readily into synthetic sequences requiring halogen-directed functionalization or transition-metal-catalyzed coupling. Its sterically accessible C2 position enables efficient derivatization for medicinal chemistry and materials applications.

Application

5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one serves as a versatile building block for the synthesis of biologically active heterocycles, particularly in medicinal chemistry and agrochemical research. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the enone functionality supports nucleophilic addition and conjugate functionalization. The molecule exhibits good bench stability and facilitates straightforward purification, making it well-suited for multi-step synthesis workflows.

Synthesis

  • Route1

    References

    • Fensome, Andrew; Bender, Reinhold; Cohen, Jeffrey; Collins, Mark A; Mackner, Valerie A; Miller, Lori L; Ullrich, John W; Winneker, Richard; Wrobel, Jay; Zhang, Puwen; Zhang, Zhiming; Zhu, Yuan Bioorganic and medicinal chemistry letters, 2002 , vol. 12, # 23 p. 3487 - 3490
  • Route2
    • In-stock
      5-Bromoindolin-2-one|CS-W002616
      20870-78-4
    • null|null
      110-18-9
    • ~17%
    • In-stock
      5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0036961
      90725-49-8

    References

    • AMGEN INC. Patent: US2007/173506 A1, 2007 ; Location in patent: Page/Page column 47-48 ;
  • Route3
    • In-stock
      5-Bromoindolin-2-one|CS-W002616
      20870-78-4
    • null|null
      74-88-4
    • ~65%
    • In-stock
      5-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0036961
      90725-49-8

    References

    • Jiang, Tao; Kuhen, Kelli L.; Wolff, Karen; Yin, Hong; Bieza, Kimberly; Caldwell, Jeremy; Bursulaya, Badry; Wu, Tom Yao-Hsing; He, Yun Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 8 p. 2105 - 2108

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

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   2.5047
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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