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5-Bromoquinoxaline

  • CAS No. 76982-23-5

  • Cat. No. CS-0038288
  • Purity≥98%
  • MDL No.None

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

5-Bromoquinoxaline|CS-0038288

Structure of 76982-23-5

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General Information

  • CAS No. 76982-23-5
  • Cat. No. CS-0038288
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂
  • Molecular Weight 209.04
  • Synonym(s) 5-BromoquinoxaL
  • SMILES C1=CC2=NC=CN=C2C(=C1)Br

Description

5-Bromoquinoxaline serves as a pivotal heterocyclic scaffold in synthetic organic chemistry, offering a robust platform for transition metal-catalyzed cross-coupling reactions. The bromine substituent enables efficient palladium-mediated functionalization, while the electron-deficient quinoxaline core facilitates conjugation and stability under standard conditions. This compound integrates seamlessly into advanced pharmaceutical intermediates and materials science applications.

Application

5-Bromoquinoxaline serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to access biaryl architectures. Its bromine substituent exhibits high reactivity in Suzuki, Stille, and Negishi couplings, facilitating the construction of complex heterocyclic systems. The quinoxaline core provides excellent planarity and electron-deficient character, enhancing utility in medicinal chemistry and materials science applications. Bench-stable and readily purified by recrystallization, it supports scalable synthesis and integration into multi-step sequences.

Synthesis

  • Route1

    References

    • Brown; Gouliaev Synthesis, 2002 , # 1 p. 83 - 86
  • Route2
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      131543-46-9
    • In-stock
      3-Bromobenzene-1,2-diamine|CS-W019000
      1575-36-6
    • ~%
    • In-stock
      5-Bromoquinoxaline|CS-0038288
      76982-23-5

    References

    • Organic Magnetic Resonance, , vol. 14, # 4 p. 300 - 304

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   25.78
  • LogP   2.3923
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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