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2,7-Dibromo-9-octyl-9H-carbazole

  • CAS No. 726169-75-1

  • Cat. No. CS-0152157
  • Purity≥95%
  • MDL No.MFCD19440901

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

2,7-Dibromo-9-octyl-9H-carbazole|CS-0152157

Structure of 726169-75-1

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General Information

  • CAS No. 726169-75-1
  • Cat. No. CS-0152157
  • Purity ≥95%
  • MDL No. MFCD19440901
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₂₃Br₂N
  • Molecular Weight 437.21
  • Synonym(s) 2,7-DibroMo-9-n-octylcarbazole
  • SMILES CCCCCCCCN1C2=C(C=CC(=C2)Br)C3=C1C=C(C=C3)Br

Description

2,7-Dibromo-9-octyl-9H-carbazole features a sterically shielded carbazole core with bromine substituents at the 2 and 7 positions, enabling efficient cross-coupling reactions. The octyl chain enhances solubility in organic media while maintaining electronic integrity. This derivative serves as a high-performance building block for solution-processable semiconductors and emissive materials in organic electronics.

Application

2,7-Dibromo-9-octyl-9H-carbazole serves as a versatile building block for the synthesis of conjugated polymers and functionalized carbazole-based materials. The dibromo substitution pattern enables efficient Pd-catalyzed cross-coupling reactions, while the octyl side chain enhances solubility and processability in solution-phase syntheses. This compound functions reliably in standard Suzuki-Miyaura and Stille coupling protocols, facilitating the construction of high-performance organic semiconductors and optoelectronic materials.

Synthesis

  • Route1

    References

    • Brunner, Klemens; Van Dijken, Addy; Boerner, Herbert; Bastiaansen, Jolanda J. A. M.; Kiggen, Nicole M. M.; Langeveld, Bea M. W. Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 6035 - 6042
  • Route2

    References

    • Kawabata, Kohsuke; Goto, Hiromasa Chemistry - A European Journal, 2012 , vol. 18, # 47 p. 15065 - 15072
  • Route3
    • 4,4'-Dibromo-2-nitro-1,1'-biphenyl|CS-0314780
      439797-69-0
    • ~%
    • In-stock
      2,7-Dibromo-9-octyl-9H-carbazole|CS-0152157
      726169-75-1

    References

    • Kawabata, Kohsuke; Goto, Hiromasa Chemistry - A European Journal, 2012 , vol. 18, # 47 p. 15065 - 15072

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

  • TPSA   4.93
  • LogP   7.68
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   7

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