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CS-W001157 4
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5-Bromo-7-chloro-1H-indole

  • CAS No. 180623-89-6

  • Cat. No. CS-0054466
  • Purity≥97%
  • MDL No.None

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

5-Bromo-7-chloro-1H-indole|CS-0054466

Structure of 180623-89-6

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General Information

  • CAS No. 180623-89-6
  • Cat. No. CS-0054466
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrClN
  • Molecular Weight 230.49
  • Synonym(s) 7-chloro-5-bromoindole
  • SMILES ClC1=CC(Br)=CC2=C1NC=C2

Description

5-Bromo-7-chloro-1H-indole features a halogenated indole core with complementary reactivity at the 5-bromo and 7-chloro positions, enabling selective cross-coupling and functionalization. This bench-stable scaffold integrates readily into bioactive molecule design, particularly in medicinal chemistry and materials science applications where electron-deficient aromatic systems are required.

Application

5-Bromo-7-chloro-1H-indole serves as a valuable building block for the synthesis of functionalized indole scaffolds in medicinal chemistry and materials science. Its complementary halogenation pattern enables selective palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with excellent functional group tolerance. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for scalable synthesis workflows.

Synthesis

  • Route1

    References

    • Wang, Le; Woods, Keith W.; Li, Qun; Barr, Kenneth J.; McCroskey, Richard W.; Hannick, Steven M.; Gherke, Laura; Credo, R. Bruce; Hui, Yu-Hua; Marsh, Kennan; Warner, Robert; Lee, Jang Y.; Zielinski-Mozng, Nicolette; Frost, David; Rosenberg, Saul H.; Sham, Hing L. Journal of Medicinal Chemistry, 2002 , vol. 45, # 8 p. 1697 - 1711
  • Route2
    • 4-Bromo-2-chloro-6-iodoaniline|CS-0608039
      56141-11-8
    • ~%
    • In-stock
      5-Bromo-7-chloro-1H-indole|CS-0054466
      180623-89-6

    References

    • Journal of Organic Chemistry, , vol. 61, # 17 p. 5804 - 5812
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 45, # 8 p. 1697 - 1711

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

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Computational Chemistry Data

  • TPSA   15.79
  • LogP   3.5838
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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