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CS-W001157 4
Total: USD 88.00

9-(4-Bromophenyl)-9H-carbazole

  • CAS No. 57102-42-8

  • Cat. No. CS-W011997
  • Molecule weight322.21
  • Purity≥98%
  • MDL No.MFCD11617969

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

9-(4-Bromophenyl)-9H-carbazole|CS-W011997

Structure of 57102-42-8

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General Information

  • CAS No. 57102-42-8
  • Cat. No. CS-W011997
  • Purity ≥98%
  • MDL No. MFCD11617969
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₂BrN
  • Molecular Weight 322.21
  • Synonym(s) 9-(4-bromophenyl)carbazole; 9-(4-Bromophenyl)-9H-carbazole
  • SMILES BrC1=CC=C(N2C3=C(C4=C2C=CC=C4)C=CC=C3)C=C1

Description

9-(4-Bromophenyl)-9H-carbazole features a brominated phenyl group fused to the carbazole core, enabling efficient coupling in cross-coupling reactions. This electron-rich scaffold serves as a robust building block for conjugated materials in organic electronics. The bromine substituent offers high reactivity under palladium catalysis, facilitating precise molecular engineering.

Application

9-(4-Bromophenyl)-9H-carbazole serves as a versatile building block for constructing biaryl scaffolds in medicinal chemistry and materials science. The bromo group enables reliable Pd-catalyzed cross-coupling reactions, including Suzuki and Stille couplings, facilitating the assembly of complex molecular architectures. Its carbazole core offers excellent stability, moderate solubility, and favorable electronic properties, making it well-suited for synthesis workflows requiring bench-stable, functionalized heterocycles.

Synthesis

  • Route1
    • In-stock
      1,4-Dibromobenzene|CS-0000003
      106-37-6
    • null|null
      86-74-8
    • ~82%
    • In-stock
      9-(4-Bromophenyl)-9H-carbazole|CS-W011997
      57102-42-8

    References

    • Lai, Wen-Yong; He, Qi-Yuan; Chen, Dao-Yong; Huang, Wei Chemistry Letters, 2008 , vol. 37, # 9 p. 986 - 987
  • Route2
    • In-stock
      4-Bromoiodobenzene|CS-W008977
      589-87-7
    • null|null
      86-74-8
    • ~93%
    • In-stock
      9-(4-Bromophenyl)-9H-carbazole|CS-W011997
      57102-42-8

    References

    • NITTO DENKO CORPORATION; SISK, David, T.; KHAN, Sazzadur, Rahman; MOCHIZUKI, Amane Patent: WO2012/37269 A1, 2012 ; Location in patent: Page/Page column 44-45 ;
  • Route3
    • In-stock
      Dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate|CS-1351147
      189999-35-7
    • null|null
      106-40-1
    • ~66%
    • In-stock
      9-(4-Bromophenyl)-9H-carbazole|CS-W011997
      57102-42-8

    References

    • Zhu, Daqian; Liu, Qi; Luo, Bingling; Chen, Meihui; Pi, Rongbiao; Huang, Peng; Wen, Shijun Advanced Synthesis and Catalysis, 2013 , vol. 355, # 11-12 p. 2172 - 2178

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

Quality Control

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Computational Chemistry Data

  • TPSA   4.93
  • LogP   5.5462
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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