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CS-W001157 4
Total: USD 88.00

6-Bromo-2,3-dihydroquinolin-4(1H)-one

  • CAS No. 76228-06-3

  • Cat. No. CS-W018961
  • Purity≥98%
  • MDL No.MFCD00600620

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

6-Bromo-2,3-dihydroquinolin-4(1H)-one|CS-W018961

Structure of 76228-06-3

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General Information

  • CAS No. 76228-06-3
  • Cat. No. CS-W018961
  • Purity ≥98%
  • MDL No. MFCD00600620
  • 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-2,3-dihydro-1H-quinolin-4-one
  • SMILES BrC2=CC=C1NCCC(C1=C2)=O

Description

6-Bromo-2,3-dihydroquinolin-4(1H)-one features a brominated dihydroquinolinone core with enhanced reactivity at the C6 position. This bench-stable heterocycle integrates readily into cross-coupling and cyclization workflows, offering efficient access to complex nitrogen-containing scaffolds in medicinal chemistry and materials synthesis.

Application

6-Bromo-2,3-dihydroquinolin-4(1H)-one serves as a versatile building block for the synthesis of biologically relevant heterocycles and pharmaceutical intermediates. Its bromine substituent enables facile palladium-catalyzed cross-coupling reactions, while the enaminone functionality supports electrophilic substitution and condensation processes. The compound exhibits good bench stability and is readily purified by crystallization, facilitating its use in multi-step synthetic sequences targeting kinase inhibitors and CNS-active compounds.

Synthesis

  • Route1

    References

    • WO2005/95326 A2, ; Page/Page column 248 ; WO 2005/095326 A2
  • Route2
    • 1-(4-Bromophenyl)azetidin-2-one|CS-0725836
      7661-25-8
    • ~92%
    • In-stock
      6-Bromo-2,3-dihydroquinolin-4(1H)-one|CS-W018961
      76228-06-3

    References

    • Lange, Jens; Bissember, Alex C.; Banwell, Martin G.; Cade, Ian A. Australian Journal of Chemistry, 2011 , vol. 64, # 4 p. 454 - 470
  • Route3
    • null|null
      875827-47-7
    • ~%
    • In-stock
      6-Bromo-2,3-dihydroquinolin-4(1H)-one|CS-W018961
      76228-06-3

    References

    • Journal of the American Chemical Society, , vol. 76, p. 5065,5067

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   2.4474
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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