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

  • CAS No. 90725-50-1

  • Cat. No. CS-0037724
  • Purity≥98%
  • MDL No.None

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

6-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0037724

Structure of 90725-50-1

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General Information

  • CAS No. 90725-50-1
  • Cat. No. CS-0037724
  • 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) 6-Bromo-3-methylindolin-2-one
  • SMILES CC1C2=CC=C(C=C2NC1=O)Br

Description

6-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one features a brominated indolinone scaffold with enhanced reactivity at the C6 position. The methyl group at C3 provides steric and electronic modulation, while the dihydroindolone core offers stability under standard conditions. This compound serves as a key intermediate in the synthesis of bioactive heterocycles, particularly in medicinal chemistry applications involving palladium-catalyzed cross-coupling reactions.

Application

6-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one serves as a versatile building block for the synthesis of biologically active indole derivatives. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the keto group facilitates nucleophilic addition and condensation processes. The molecule exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • 2-(4-Bromo-2-nitrophenyl)propanoic acid|CS-0664597
      400620-76-0
    • ~94%
    • In-stock
      6-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0037724
      90725-50-1

    References

    • Bender, David Michael; Forman, Scott Louis; Jones, Winton Dennis; Smith, Daryl Lynn; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael Patent: US2003/225127 A1, 2003 ; Location in patent: Page 14 ;
  • Route2

    References

    • Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki Patent: EP2669270 A1, 2013 ; Location in patent: Paragraph 0566-0567 ;
  • Route3
    • null|null
      65617-24-5
    • ~96%
    • In-stock
      6-Bromo-3-methyl-2,3-dihydro-1H-indol-2-one|CS-0037724
      90725-50-1

    References

    • Atwal, Karnail S.; Ferrara, Francis N.; Ding, Charles Z.; Grover, Gary J.; Sleph, Paul G.; Dzwonczyk, Steven; Baird, Anne J.; Normandin, Diane E. Journal of Medicinal Chemistry, 1996 , vol. 39, # 1 p. 304 - 313

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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