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CS-W001157 4
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3-Bromo-8-chloroimidazo[1,2-a]pyrazine

  • CAS No. 143591-61-1

  • Cat. No. CS-W019641
  • Purity≥97%
  • MDL No.MFCD09909653

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

3-Bromo-8-chloroimidazo[1,2-a]pyrazine|CS-W019641

Structure of 143591-61-1

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General Information

  • CAS No. 143591-61-1
  • Cat. No. CS-W019641
  • Purity ≥97%
  • MDL No. MFCD09909653
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃BrClN₃
  • Molecular Weight 232.47
  • Synonym(s) 8-Chloro-3-bromoimidazo[1,2-a]pyrazine
  • SMILES ClC1=NC=CN2C1=NC=C2Br

Description

3-Bromo-8-chloroimidazo[1,2-a]pyrazine is a halogenated heterocyclic scaffold featuring complementary electrophilic sites at the 3- and 8-positions. This electron-deficient core enables selective cross-coupling reactions and serves as a key building block in medicinal chemistry. The molecule exhibits good stability under standard conditions and facilitates direct functionalization in late-stage diversification.

Application

3-Bromo-8-chloroimidazo[1,2-a]pyrazine serves as a versatile heterocyclic building block for medicinal chemistry and materials science applications. The molecule enables palladium-catalyzed cross-coupling reactions due to its dual halogen functionality, with bromine at C3 offering high reactivity in Suzuki-Miyaura and Buchwald-Hartwig transformations. Its bench-stable nature and orthogonal reactivity profile facilitate efficient diversification of imidazopyrazine scaffolds in multi-step syntheses.

Synthesis

  • Route1

    References

    • BIOFOCUS DPI LIMITED Patent: WO2009/24585 A2, 2009 ; Location in patent: Page/Page column 46 ;
  • Route2
    • 8-Chloroimidazo[1,2-a]pyrazine hydrobromide|CS-1719385
      937790-53-9
    • ~90%
    • In-stock
      3-Bromo-8-chloroimidazo[1,2-a]pyrazine|CS-W019641
      143591-61-1

    References

    • Schering Corporation Patent: US2007/117804 A1, 2007 ; Location in patent: Page/Page column 47 ; US 20070117804 A1
  • Route3
    • In-stock
      8-Chloroimidazo[1,2-a]pyrazine|CS-W004033
      69214-33-1
    • ~%
    • In-stock
      3-Bromo-8-chloroimidazo[1,2-a]pyrazine|CS-W019641
      143591-61-1
    • 3,8-Dibromoimidazo[1,2-a]pyrazine|CS-0085065
      936361-36-3

    References

    • WO2010/69684 A1, ; Page/Page column 97 ;

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   30.19
  • LogP   2.1452
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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