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CS-W001157 4
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Methyl 5-bromopyrimidine-2-carboxyate

  • CAS No. 89581-38-4

  • Cat. No. CS-W004847
  • Purity≥98%
  • MDL No.MFCD11111606

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

Methyl 5-bromopyrimidine-2-carboxyate|CS-W004847

Structure of 89581-38-4

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General Information

  • CAS No. 89581-38-4
  • Cat. No. CS-W004847
  • Purity ≥98%
  • MDL No. MFCD11111606
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) Methyl5-bromopyrimidine-2-carboxyate
  • SMILES COC(C1=NC=C(C=N1)Br)=O

Description

Methyl 5-bromopyrimidine-2-carboxyate features a bromine substituent at the 5-position and a methyl ester group at the 2-position of a pyrimidine core. This electron-deficient heterocycle serves as a key building block for medicinal chemistry, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. The molecule exhibits robust stability under standard bench conditions and integrates readily into complex molecular architectures.

Application

Methyl 5-bromopyrimidine-2-carboxyate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions at the C5 position. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the ester group offers compatibility with base-sensitive transformations. Its bench-stable nature and ease of purification facilitate integration into multi-step synthetic sequences for pharmaceutical intermediates and agrochemical scaffolds.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      5-Bromo-2-pyrimidinecarboxylic acid|CS-W008708
      37131-87-6
    • ~57%
    • In-stock
      Methyl 5-bromopyrimidine-2-carboxyate|CS-W004847
      89581-38-4

    References

    • WO2005/28452 A1, ; Page/Page column 88 ; WO 2005/028452 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-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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