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CS-W001157 4
Total: USD 88.00

5,8-Dibromoquinoxaline

  • CAS No. 148231-12-3

  • Cat. No. CS-W005900
  • Purity≥95%
  • MDL No.MFCD18448005

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

5,8-Dibromoquinoxaline|CS-W005900

Structure of 148231-12-3

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General Information

  • CAS No. 148231-12-3
  • Cat. No. CS-W005900
  • Purity ≥95%
  • MDL No. MFCD18448005
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄Br₂N₂
  • Molecular Weight 287.94
  • Synonym(s) 5,8-dibromo-Quinoxaline
  • SMILES BrC1=CC=C(Br)C2=C1N=CC=N2

Description

5,8-Dibromoquinoxaline delivers a sterically constrained, electron-deficient heteroaromatic scaffold ideal for cross-coupling applications. The dibromo substitution pattern enables sequential functionalization, while the quinoxaline core provides robust thermal stability and enhanced solubility in polar aprotic solvents. This compound serves as a key intermediate in the synthesis of advanced materials and bioactive heterocycles.

Application

5,8-Dibromoquinoxaline serves as a versatile building block for the synthesis of functionalized heterocycles and pharmaceutical intermediates. Its brominated positions enable palladium-catalyzed cross-coupling reactions with broad functional group tolerance, facilitating efficient access to biaryl and extended π-conjugated systems. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for scalable synthetic workflows in medicinal chemistry and materials science applications.

Synthesis

  • Route1
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      95-54-5
    • ~%
    • In-stock
      5,8-Dibromoquinoxaline|CS-W005900
      148231-12-3

    References

    • DaSilveira Neto, Brenno A.; Lopes, Aline S.; Wuest, Martina; Costa, Valentim E. U.; Ebeling, Guenter; Dupont, Jairton Tetrahedron Letters, 2005 , vol. 46, # 40 p. 6843 - 6846
  • Route2
    • null|null
      131543-46-9
    • In-stock
      3,6-Dibromobenzene-1,2-diamine|CS-W005872
      69272-50-0
    • ~99%
    • In-stock
      5,8-Dibromoquinoxaline|CS-W005900
      148231-12-3

    References

    • IDEMITSU KOSAN CO., LTD. Patent: EP1749823 A1, 2007 ; Location in patent: Page/Page column 30 ;
  • Route3

    References

    • Popere, Bhooshan C.; Della Pelle, Andrea M.; Thayumanavan Macromolecules, 2011 , vol. 44, # 12 p. 4767 - 4776

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   25.78
  • LogP   3.1548
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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