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CS-W001157 4
Total: USD 88.00

6-Bromo-2,3,4,9-tetrahydro-1H-carbazole

  • CAS No. 21865-50-9

  • Cat. No. CS-0096539
  • Purity≥95%
  • MDL No.MFCD00094989

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

6-Bromo-2,3,4,9-tetrahydro-1H-carbazole|CS-0096539

Structure of 21865-50-9

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General Information

  • CAS No. 21865-50-9
  • Cat. No. CS-0096539
  • Purity ≥95%
  • MDL No. MFCD00094989
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₂BrN
  • Molecular Weight 250.13
  • Synonym(s) 6-BROMO-1,2,3,4-TETRAHYDROCARBAZOLE
  • SMILES BrC1=CC2=C(NC3=C2CCCC3)C=C1

Description

6-Bromo-2,3,4,9-tetrahydro-1H-carbazole offers a brominated heterocyclic scaffold ideal for cross-coupling transformations. The tetrahydrocarbazole core provides enhanced solubility and stability compared to fully aromatic analogs, while the pendant bromine enables efficient palladium-catalyzed functionalization. This intermediate integrates readily into complex molecular architectures used in medicinal chemistry and materials science.

Application

6-Bromo-2,3,4,9-tetrahydro-1H-carbazole serves as a versatile building block for the synthesis of biologically relevant heterocycles and pharmaceutical intermediates. Its bromine substituent enables facile cross-coupling reactions, including Suzuki and Stille couplings, while the tetrahydrocarbazole core provides a stable, bench-stable scaffold with favorable functional group tolerance. This compound functions effectively in late-stage diversification strategies within medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      108-94-1
    • In-stock
      (4-Bromophenyl)hydrazine|CS-0060253
      589-21-9
    • ~95%
    • In-stock
      6-Bromo-2,3,4,9-tetrahydro-1H-carbazole|CS-0096539
      21865-50-9

    References

    • Tetrahedron Letters, , vol. 52, # 34 p. 4417 - 4420
  • Route2
    • null|null
      117489-28-8
    • ~96%
    • In-stock
      6-Bromo-2,3,4,9-tetrahydro-1H-carbazole|CS-0096539
      21865-50-9

    References

    • US8080566 B1, ; Page/Page column 53-54 ;
  • Route3
    • In-stock
      (4-Bromophenyl)hydrazine hydrochloride|CS-W013083
      622-88-8
    • null|null
      108-94-1
    • ~73%
    • In-stock
      6-Bromo-2,3,4,9-tetrahydro-1H-carbazole|CS-0096539
      21865-50-9

    References

    • WO2009/103022 A1, ; Page/Page column 62 ;

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   15.79
  • LogP   3.8092
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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