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CS-W001157 4
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Methyl 3,6-dibromopyrazine-2-carboxylate

  • CAS No. 13301-04-7

  • Cat. No. CS-W003819
  • Purity≥98%
  • MDL No.MFCD11976863

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

Methyl 3,6-dibromopyrazine-2-carboxylate|CS-W003819

Structure of 13301-04-7

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General Information

  • CAS No. 13301-04-7
  • Cat. No. CS-W003819
  • Purity ≥98%
  • MDL No. MFCD11976863
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄Br₂N₂O₂
  • Molecular Weight 295.92
  • Synonym(s) None
  • SMILES COC(=O)c1nc(Br)cnc1Br

Description

Methyl 3,6-dibromopyrazine-2-carboxylate features a dibrominated pyrazine core with a methyl ester at the C2 position, enabling direct incorporation into heterocyclic synthesis. The electron-deficient framework supports palladium-catalyzed cross-coupling reactions, while the sterically accessible bromine sites facilitate sequential functionalization. This bench-stable reagent delivers high regioselectivity in constructing complex nitrogen-containing scaffolds.

Application

Methyl 3,6-dibromopyrazine-2-carboxylate serves as a versatile building block for the synthesis of brominated pyrazine derivatives. Its dual bromo substituents enable sequential cross-coupling reactions, while the ester group facilitates downstream functionalization. The compound exhibits good bench stability and is compatible with palladium-catalyzed transformations, making it valuable in constructing heterocyclic scaffolds for medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael Patent: US2011/59118 A1, 2011 ; Location in patent: Page/Page column 84-85 ;
  • Route2

    References

    • US2011/59118 A1, ;
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 6 p. 2266 - 2270

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   1.7882
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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