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CS-W001157 4
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7-Bromo-2-chloroquinoxaline

  • CAS No. 89891-65-6

  • Cat. No. CS-W019688
  • Purity≥97%
  • MDL No.MFCD02955309

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

7-Bromo-2-chloroquinoxaline|CS-W019688

Structure of 89891-65-6

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General Information

  • CAS No. 89891-65-6
  • Cat. No. CS-W019688
  • Purity ≥97%
  • MDL No. MFCD02955309
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄BrClN₂
  • Molecular Weight 243.49
  • Synonym(s) 2-chloro-7-bromo-quinoxaline
  • SMILES ClC1=NC2=CC(Br)=CC=C2N=C1

Description

7-Bromo-2-chloroquinoxaline features a fused bicyclic core with complementary halogen substituents enabling selective cross-coupling reactions. The electron-deficient quinoxaline scaffold supports efficient palladium-catalyzed transformations, while the bromo and chloro groups offer orthogonal reactivity for sequential functionalization. This compound serves as a robust building block in synthetic pathways targeting bioactive heterocycles and advanced materials.

Application

7-Bromo-2-chloroquinoxaline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The bromo group at the 7-position facilitates efficient Suzuki, Stille, or Negishi coupling, while the chloro group at the 2-position offers orthogonal reactivity for sequential functionalization. Its stability under standard reaction conditions and ease of purification make it ideal for constructing complex heterocyclic scaffolds in API development and advanced organic synthesis.

Synthesis

  • Route1

    References

    • Nishimura, Nobuko; Siegmund, Aaron; Liu, Longbin; Yang, Kevin; Bryan, Marian C.; Andrews, Kristin L.; Bo, Yunxin; Booker, Shon K.; Caenepeel, Sean; Freeman, Daniel; Liao, Hongyu; McCarter, John; Mullady, Erin L.; San Miguel, Tisha; Subramanian, Raju; Tamayo, Nuria; Wang, Ling; Whittington, Douglas A.; Zalameda, Leeanne; Zhang, Nancy; Hughes, Paul E.; Norman, Mark H. Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4735 - 4751
  • Route2
    • null|null
      924-44-7
    • null|null
      95-54-5
    • ~56%
    • In-stock
      7-Bromo-2-chloroquinoxaline|CS-W019688
      89891-65-6

    References

    • ELI LILLY AND COMPANY Patent: WO2005/92894 A1, 2005 ; Location in patent: Page/Page column 26 ; WO 2005/092894 A1
  • Route3

    References

    • WO2011/26579 A1, ; WO 2011/026579 A1

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   3.0457
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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