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3-Chloro-5-iodopyrazin-2-amine

  • CAS No. 1252597-70-8

  • Cat. No. CS-0051408
  • Molecule weight255.44
  • Purity≥98%
  • MDL No.None

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

3-Chloro-5-iodopyrazin-2-amine|CS-0051408

Structure of 1252597-70-8

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General Information

  • CAS No. 1252597-70-8
  • Cat. No. CS-0051408
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₃ClIN₃
  • Molecular Weight 255.44
  • Synonym(s) 5-chloro-3-iodopyrazin-2-amine
  • SMILES NC1=NC=C(I)N=C1Cl

Description

3-Chloro-5-iodopyrazin-2-amine features a pyrazine core bearing chlorine and iodine substituents at the 3- and 5-positions, respectively, enabling direct functionalization in cross-coupling reactions. This electron-deficient heterocycle integrates readily into pharmaceutical scaffolds, offering enhanced metabolic stability and tunable polarity. The iodide group serves as a high-reactivity handle for palladium-catalyzed transformations under standard conditions.

Application

3-Chloro-5-iodopyrazin-2-amine serves as a versatile building block for the synthesis of functionalized pyrazine scaffolds in medicinal chemistry and agrochemical research. Its complementary halogen handles enable sequential cross-coupling reactions, including Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig aminations, facilitating rapid diversification. The molecule exhibits good bench stability and is compatible with standard purification methods, making it well-suited for iterative synthetic workflows.

Synthesis

  • Route1

    References

    • Janssen Pharmaceutica NV Patent: US2012/329792 A1, 2012 ; Location in patent: Page/Page column 33 ;

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   51.8
  • LogP   1.3168
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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