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Methyl 3-bromopyrazine-2-carboxylate

  • CAS No. 51171-02-9

  • Cat. No. CS-D1608
  • Purity≥98%
  • MDL No.MFCD08753935

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

Methyl 3-bromopyrazine-2-carboxylate|CS-D1608

Structure of 51171-02-9

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General Information

  • CAS No. 51171-02-9
  • Cat. No. CS-D1608
  • Purity ≥98%
  • MDL No. MFCD08753935
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) Pyrazinecarboxylic acid, 3-bromo-, methyl ester; 2-Pyrazinecarboxylic acid, 3-bromo-, methyl ester
  • SMILES O=C(C1=NC=CN=C1Br)OC

Description

Methyl 3-bromopyrazine-2-carboxylate is a halogenated pyrazine derivative featuring a bromine atom at the 3-position and a methyl ester at the 2-position. This electron-deficient heterocycle integrates readily into cross-coupling reactions, enabling efficient access to functionalized pyrazine scaffolds under palladium-catalyzed conditions. The ester group enhances solubility and facilitates downstream derivatization.

Application

Methyl 3-bromopyrazine-2-carboxylate serves as a versatile building block in medicinal chemistry and heterocyclic synthesis. The bromine at the C3 position enables palladium-catalyzed cross-coupling reactions, while the ester group facilitates further functionalization or hydrolysis to the carboxylic acid. Its stability under standard reaction conditions and compatibility with diverse coupling partners make it a practical choice for constructing complex pyrazine-based scaffolds in API development.

Synthesis

  • Route1

    References

    • BAYER PHARMACEUTICALS CORPORATION Patent: WO2006/49681 A2, 2006 ; Location in patent: Page/Page column 45-46 ; WO 2006/049681 A2
  • Route2

    References

    • Duan, Hongliang; Ning, Mengmeng; Chen, Xiaoyan; Zou, Qingan; Zhang, Liming; Feng, Ying; Zhang, Lina; Leng, Ying; Shen, Jianhua Journal of Medicinal Chemistry, 2012 , vol. 55, # 23 p. 10475 - 10489

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   1.0257
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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