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CS-W001157 4
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5-Bromo-6-methylpyrazin-2-amine

  • CAS No. 74290-69-0

  • Cat. No. CS-W006668
  • Molecule weight188.03
  • Purity≥98%
  • MDL No.MFCD08705763

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

5-Bromo-6-methylpyrazin-2-amine|CS-W006668

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General Information

  • CAS No. 74290-69-0
  • Cat. No. CS-W006668
  • Purity ≥98%
  • MDL No. MFCD08705763
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆BrN₃
  • Molecular Weight 188.03
  • Synonym(s) 5-BROMO-6-METHYLPYRAZIN-2-YLAMINE
  • SMILES CC1=C(Br)N=CC(N)=N1

Description

5-Bromo-6-methylpyrazin-2-amine features a brominated pyrazine core with a methyl group at the 6-position and an amino substituent at the 2-position, enabling direct functionalization in late-stage diversification. The electron-deficient pyrazine ring facilitates coupling reactions under mild conditions, while the methyl and bromo groups provide steric and electronic control for selective transformations. This compound serves as a key scaffold in medicinal chemistry for kinase inhibitors and bioactive heterocycles.

Application

5-Bromo-6-methylpyrazin-2-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of complex heterocyclic scaffolds. The bromine atom facilitates efficient functionalization via Suzuki, Stille, or Negishi coupling, while the pyrazine core provides a rigid, electron-deficient platform suitable for target-oriented synthesis. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan Patent: WO2013/174822 A1, 2013 ; Location in patent: Page/Page column 86 ;
  • Route2

    References

    • Sato, Nobuhiro Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 143 - 147
  • Route3

    References

    • Journal of Heterocyclic Chemistry, , vol. 17, p. 143 - 147

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
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   51.8
  • LogP   1.12972
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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