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3-Chloropyrazin-2(1H)-one

  • CAS No. 105985-17-9

  • Cat. No. CS-0155546
  • Purity≥97%
  • MDL No.MFCD18427098

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

3-Chloropyrazin-2(1H)-one|CS-0155546

Structure of 105985-17-9

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General Information

  • CAS No. 105985-17-9
  • Cat. No. CS-0155546
  • Purity ≥97%
  • MDL No. MFCD18427098
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₃ClN₂O
  • Molecular Weight 130.53
  • Synonym(s) oropyrazin-2-oL
  • SMILES C1=CNC(=O)C(=N1)Cl

Description

3-Chloropyrazin-2(1H)-one features a chlorinated pyrazinone core with enhanced electrophilicity at the C3 position, enabling selective nucleophilic substitution reactions. This bench-stable heterocycle integrates readily into bioactive scaffolds and serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and antimicrobial agents.

Application

3-Chloropyrazin-2(1H)-one serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C3 position via nucleophilic substitution. Its pyrazinone core provides a stable, electron-deficient heterocyclic scaffold compatible with diverse coupling reactions. The chlorine substituent facilitates palladium-catalyzed cross-coupling and amide formation, offering efficient access to substituted pyrazine derivatives. Bench-stable and readily purified by recrystallization, it functions as a reliable intermediate in API synthesis and combinatorial library generation.

Synthesis

  • Route1

    References

    • MERCK SERONO S.A. GENEVA; POHIN, Danig; SWINNEN, Dominique Patent: WO2012/52420 A1, 2012 ; Location in patent: Page/Page column 28-29 ;

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   45.75
  • LogP   0.4233
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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