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CS-W001157 4
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2-Bromoquinoxaline

  • CAS No. 36856-91-4

  • Cat. No. CS-W008094
  • Purity≥98%
  • MDL No.MFCD07368206

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

2-Bromoquinoxaline|CS-W008094

Structure of 36856-91-4

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General Information

  • CAS No. 36856-91-4
  • Cat. No. CS-W008094
  • Purity ≥98%
  • MDL No. MFCD07368206
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂
  • Molecular Weight 209.04
  • Synonym(s) quinoxaline, 2-bromo-
  • SMILES BrC2=NC1=CC=CC=C1N=C2

Description

2-Bromoquinoxaline is a bench-stable, electron-deficient heterocycle featuring a bromine atom at the 2-position, enabling direct functionalization in cross-coupling reactions. This configuration enhances reactivity in palladium-catalyzed transformations while maintaining compatibility with diverse reaction conditions. The fused bicyclic core provides structural rigidity and polarity suitable for applications in medicinal chemistry and materials science.

Application

2-Bromoquinoxaline serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Stille couplings. Its bromine substituent facilitates efficient functionalization at the C2 position, while the quinoxaline core provides robust stability and planarity advantageous for constructing heterocyclic scaffolds. The compound exhibits excellent bench stability and compatibility with a wide range of reaction conditions, making it well-suited for medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Voets, Marieke; Antes, Iris; Scherer, Christiane; Mueller-Vieira, Ursula; Biemel, Klaus; Barassin, Catherine; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W. Journal of Medicinal Chemistry, 2005 , vol. 48, # 21 p. 6632 - 6642

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

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