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CS-W001157 4
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4-(Pyrazin-2-yl)benzaldehyde

  • CAS No. 127406-08-0

  • Cat. No. CS-0170959
  • Purity≥98%
  • MDL No.None

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

4-(Pyrazin-2-yl)benzaldehyde|CS-0170959

Structure of 127406-08-0

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General Information

  • CAS No. 127406-08-0
  • Cat. No. CS-0170959
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈N₂O
  • Molecular Weight 184.19
  • Synonym(s) 4-PYRAZIN-2-YLBENZALDEHYDE
  • SMILES C1=C(C=CC(=C1)C2=CN=CC=N2)C=O

Description

4-(Pyrazin-2-yl)benzaldehyde features a pyrazine ring linked to a benzaldehyde moiety, creating a rigid, electron-deficient scaffold ideal for transition metal-catalyzed coupling reactions. This conjugated system enhances planarity and facilitates π-stacking in supramolecular architectures. The aldehyde group enables direct functionalization via nucleophilic addition or oxime formation, supporting rapid access to bioactive heterocycles and advanced ligands.

Application

4-(Pyrazin-2-yl)benzaldehyde serves as a versatile building block for conjugated heteroaromatic systems, enabling efficient construction of biaryl scaffolds via Suzuki-Miyaura and Ullmann-type coupling reactions. The aldehyde functionality facilitates direct incorporation into imine-based libraries and oxime derivatizations, while the pyrazine ring provides enhanced solubility and metabolic stability. Bench-stable and amenable to standard purification methods, it functions effectively in multi-step synthesis of pharmaceutical intermediates and functional materials.

Synthesis

  • Route1

    References

    • US2005/250713 A1, ; Page/Page column 29-30 ;
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 3 p. 631 - 634

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-H319
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   42.85
  • LogP   1.9561
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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