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Methyl 6-bromo-3-chloropyrazine-2-carboxylate

  • CAS No. 1256921-67-1

  • Cat. No. CS-0098103
  • Molecule weight251.47
  • Purity≥95%
  • MDL No.MFCD18250172

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

Methyl 6-bromo-3-chloropyrazine-2-carboxylate|CS-0098103

Structure of 1256921-67-1

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General Information

  • CAS No. 1256921-67-1
  • Cat. No. CS-0098103
  • Purity ≥95%
  • MDL No. MFCD18250172
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄BrClN₂O₂
  • Molecular Weight 251.47
  • Synonym(s) Methyl 6-bromo-3-chloro-2-pyrazinecarboxylate
  • SMILES O=C(C1=NC(Br)=CN=C1Cl)OC

Description

Methyl 6-bromo-3-chloropyrazine-2-carboxylate is a halogenated pyrazine derivative featuring complementary reactive sites for cross-coupling and functionalization. The bromo group at C6 enables palladium-catalyzed coupling, while the chloro substituent at C3 offers orthogonal reactivity. This dual-halogenation pattern facilitates sequential derivatization in complex molecule synthesis, particularly in medicinal chemistry and agrochemical development.

Application

Methyl 6-bromo-3-chloropyrazine-2-carboxylate serves as a versatile heterocyclic building block for the synthesis of pharmaceutical intermediates and agrochemical scaffolds. Its orthogonal halogenation pattern enables sequential cross-coupling reactions, including Suzuki and Stille couplings, with high chemoselectivity. The ester functionality supports further derivatization, while the pyrazine core provides metabolic stability and favorable physicochemical properties in drug discovery applications.

Synthesis

  • Route1

    References

    • WO2010/141275 A1, ; Page/Page column 39 ;

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   52.08
  • LogP   1.6791
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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