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CS-W001157 4
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1-Bromo-9H-carbazole

  • CAS No. 16807-11-7

  • Cat. No. CS-W007242
  • Molecule weight246.10
  • Purity≥98%
  • MDL No.MFCD18450164

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

1-Bromo-9H-carbazole|CS-W007242

Structure of 16807-11-7

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General Information

  • CAS No. 16807-11-7
  • Cat. No. CS-W007242
  • Purity ≥98%
  • MDL No. MFCD18450164
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₈BrN
  • Molecular Weight 246.10
  • Synonym(s) 1-Bromocarbazole fandachem
  • SMILES BrC1=CC=CC2=C1NC3=C2C=CC=C3

Description

1-Bromo-9H-carbazole features a bromine atom at the 1-position of the carbazole scaffold, enabling direct functionalization in cross-coupling reactions. The electron-rich aromatic system supports stable incorporation into conjugated materials. This bench-stable reagent facilitates efficient access to carbazole-based architectures in organic synthesis and materials science applications.

Application

1-Bromo-9H-carbazole serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl and heteroaryl scaffolds. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the carbazole core offers inherent stability and π-conjugation valuable in materials science and medicinal chemistry applications. Its bench-stable crystalline form facilitates handling and purification, making it ideal for iterative synthesis workflows.

Synthesis

  • Route1

    References

    • Liu, Ching-Yuan; Knochel, Paul Organic Letters, 2005 , vol. 7, # 13 p. 2543 - 2546
  • Route2
    • 8-Bromo-2,3,4,9-tetrahydro-1h-carbazole|CS-0265986
      27372-41-4
    • ~%
    • In-stock
      1-Bromo-9H-carbazole|CS-W007242
      16807-11-7

    References

    • Barclay; Campbell Journal of the Chemical Society, 1945 , p. 530,532
  • Route3
    • null|null
      86-74-8
    • ~9%
    • In-stock
      1-Bromo-9H-carbazole|CS-W007242
      16807-11-7
    • In-stock
      3-Bromocarbazole|CS-W008617
      1592-95-6

    References

    • Bonesi, Sergio M.; Erra-Balsells, Rosa Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 7 p. 1583 - 1595

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 : 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   15.79
  • LogP   4.0836
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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