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5-Bromo-2,3-dihydro-1H-indene

  • CAS No. 6134-54-9

  • Cat. No. CS-0137904
  • Purity≥97%
  • MDL No.MFCD09842508

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

5-Bromo-2,3-dihydro-1H-indene|CS-0137904

Structure of 6134-54-9

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General Information

  • CAS No. 6134-54-9
  • Cat. No. CS-0137904
  • Purity ≥97%
  • MDL No. MFCD09842508
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉Br
  • Molecular Weight 197.07
  • Synonym(s) 5-Bromoindane
  • SMILES BrC1=CC2=C(CCC2)C=C1

Description

5-Bromo-2,3-dihydro-1H-indene is a brominated indene derivative featuring a reactive dihydroindene core with enhanced stability and solubility in organic solvents. This compound serves as a key intermediate in synthetic routes to functionalized aromatic systems, particularly in palladium-catalyzed cross-coupling reactions. The bromine substituent enables efficient C–C bond formation under mild conditions, while the saturated ring system minimizes side reactivity. Its bench-stable nature simplifies handling during multi-step syntheses.

Application

5-Bromo-2,3-dihydro-1H-indene serves as a versatile building block in synthetic organic chemistry, offering a stable, bench-compatible platform for palladium-catalyzed cross-coupling reactions. The bromo group enables efficient Suzuki, Stille, and Negishi coupling transformations, while the dihydroindene core provides structural rigidity and compatibility with diverse functional groups. Its predictable reactivity and ease of purification make it a practical choice for constructing complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Michelotti, Enrique L.; Moffett, Kristofer K.; Nguyen, Duyan; Kelly, Martha J.; Shetty, Rupa; Chai, Xiaomei; Northrop, Katrina; Namboodiri, Variketta; Campbell, Brandon; Flynn, Gary A.; Fujimoto, Ted; Hollinger, Frank P.; Bukhtiyarova, Marina; Springman, Eric B.; Karpusas, Michael Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5274 - 5279
  • Route2
    • null|null
      617-86-7
    • In-stock
      5-Bromo-2,3-dihydro-1H-inden-1-one|CS-W008687
      34598-49-7
    • ~63%
    • In-stock
      5-Bromo-2,3-dihydro-1H-indene|CS-0137904
      6134-54-9

    References

    • GLAXOSMITHKLINE LLC; ADAMS, Nicholas, D.; AQUINO, Christopher, Joseph; CHAUDHARI, Amita, M.; GHERGUROVICH, Jonathan, M.; KIESOW, Terence, John; PARRISH, Cynthia, A.; REIF, Alexander, Joseph; WIGGALL, Kenneth Patent: WO2011/103546 A1, 2011 ; Location in patent: Page/Page column 149-150 ; WO 2011/103546 A1
  • Route3

    References

    • SANOFI-AVENTIS; GEORGE, Pascal; HALL, Daniel; HARTUNG, Ryan; KOSLEY, JR., Raymond W.; SCOTESE, Anthony C. Patent: WO2011/34828 A1, 2011 ; Location in patent: Page/Page column 45 ; WO 2011/034828 A1

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-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P341-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.9378
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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