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CS-W001157 4
Total: USD 88.00

2-Bromopyrimidine-4-carbonitrile

  • CAS No. 1209459-16-4

  • Cat. No. CS-W021628
  • Purity≥98%
  • MDL No.MFCD13193321

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

2-Bromopyrimidine-4-carbonitrile|CS-W021628

Structure of 1209459-16-4

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General Information

  • CAS No. 1209459-16-4
  • Cat. No. CS-W021628
  • Purity ≥98%
  • MDL No. MFCD13193321
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₂BrN₃
  • Molecular Weight 183.99
  • Synonym(s) 2-Bromo-4-pyrimidinecarbonitrile
  • SMILES BrC1=NC(=CC=N1)C#N

Description

2-Bromopyrimidine-4-carbonitrile features a bromine atom at the 2-position and a nitrile group at the 4-position on a pyrimidine scaffold, delivering a potent electrophilic handle for nucleophilic substitution. This dual functionality enables efficient coupling in cross-coupling reactions and facilitates the synthesis of complex heterocyclic architectures. The molecule exhibits enhanced reactivity due to the electron-withdrawing nature of both substituents, allowing for selective functionalization under mild conditions. Its bench-stable form simplifies handling in synthetic workflows.

Application

2-Bromopyrimidine-4-carbonitrile serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its reactive bromine and electron-deficient pyrimidine core. The nitrile group provides additional handle for functionalization, while the molecule exhibits bench stability and compatibility with standard purification methods. It functions effectively in the construction of bioactive scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1
    • 2-Oxo-2,3-dihydropyrimidine-4-carbaldehyde oxime|CS-0045758
      7460-56-2
    • ~%
    • In-stock
      2-Bromopyrimidine-4-carbonitrile|CS-W021628
      1209459-16-4

    References

    • WO2013/107291 A1, ; Page/Page column 74 ;
  • Route2

    References

    • US2013/190249 A1, ; Page/Page column ;

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   49.57
  • LogP   1.11078
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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