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CS-W001157 4
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5-bromo-3-(2-(trimethylsilyl)ethynyl)pyrazin-2-amine

  • CAS No. 875781-41-2

  • Cat. No. CS-M3193
  • Purity≥97%
  • MDL No.MFCD16660032

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

5-bromo-3-(2-(trimethylsilyl)ethynyl)pyrazin-2-amine|CS-M3193

Structure of 875781-41-2

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General Information

  • CAS No. 875781-41-2
  • Cat. No. CS-M3193
  • Purity ≥97%
  • MDL No. MFCD16660032
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₂BrN₃Si
  • Molecular Weight 270.20
  • Synonym(s) 5-Bromo-3-[(trimethylsilyl)ethynyl]pyrazin-2-amine; 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine
  • SMILES NC1=NC=C(Br)N=C1C#C[Si](C)(C)C

Description

5-Bromo-3-(2-(trimethylsilyl)ethynyl)pyrazin-2-amine features a sterically shielded trimethylsilyl-protected alkyne, enabling stable coupling in Sonogashira reactions. The electron-deficient pyrazine core pairs with the bromo and amine functionalities for efficient cross-coupling and modular derivatization in medicinal chemistry and materials science applications.

Application

5-Bromo-3-(2-(trimethylsilyl)ethynyl)pyrazin-2-amine serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions via its bromo and silyl-protected alkyne functionalities. The trimethylsilyl group provides excellent bench stability and facilitates subsequent desilylation or Sonogashira coupling under mild conditions. Its orthogonality and functional group tolerance make it ideal for constructing complex heterocyclic scaffolds and bioactive molecules.

Synthesis

  • Route1
    • In-stock
      Amino-3,5-dibromopyrazine|CS-D1346
      24241-18-7
    • null|null
      1066-54-2
    • ~88%
    • In-stock
      5-bromo-3-(2-(trimethylsilyl)ethynyl)pyrazin-2-amine|CS-M3193
      875781-41-2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 3 p. 693 - 698

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   51.8
  • LogP   2.0502
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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