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CS-W001157 4
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5-Bromo-2-pyrimidinecarboxylic acid

  • CAS No. 37131-87-6

  • Cat. No. CS-W008708
  • Purity≥98%
  • MDL No.MFCD00496793

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

5-Bromo-2-pyrimidinecarboxylic acid|CS-W008708

Structure of 37131-87-6

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General Information

  • CAS No. 37131-87-6
  • Cat. No. CS-W008708
  • Purity ≥98%
  • MDL No. MFCD00496793
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrN₂O₂
  • Molecular Weight 202.99
  • Synonym(s) 5-Bromopyrimidine-2-carboxylic acid; T6N CNJ BVQ EE [WLN]
  • SMILES O=C(C1=NC=C(Br)C=N1)O

Description

5-Bromo-2-pyrimidinecarboxylic acid features a bromine substituent at the 5-position of a pyrimidine core, enhancing its reactivity in cross-coupling transformations. The carboxylic acid group provides a handle for derivatization and conjugation. This compound serves as a key building block in medicinal chemistry and materials science due to its stability under standard conditions and compatibility with diverse synthetic protocols.

Application

5-Bromo-2-pyrimidinecarboxylic acid serves as a versatile building block for the synthesis of heterocyclic scaffolds and pharmaceutical intermediates. Its bromo group enables palladium-catalyzed cross-coupling reactions, while the carboxylic acid facilitates derivatization via amide formation or esterification. The compound exhibits good bench stability and functional group tolerance, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2006/125958 A1, 2006 ; Location in patent: Page/Page column 102-103 ; WO 2006/125958 A1
  • Route2
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      124-38-9
    • In-stock
      5-Bromo-2-iodopyrimidine|CS-D0840
      183438-24-6
    • ~%
    • In-stock
      5-Bromo-2-pyrimidinecarboxylic acid|CS-W008708
      37131-87-6

    References

    • Bourdonnec, Bertrand Le; Windh, Rolf T.; Leister, Lara K.; Zhou, Q. Jean; Ajello, Christopher W.; Gu, Minghua; Chu, Guo-Hua; Tuthill, Paul A.; Barker, William M.; Koblish, Michael; Wiant, Daniel D.; Graczyk, Thomas M.; Belanger, Serge; Cassel, Joel A.; Feschenko, Marina S.; Brogdon, Bernice L.; Smith, Steven A.; Derelanko, Michael J.; Kutz, Steve; Little, Patrick J.; Dehaven, Robert N.; DeHaven-Hudkins, Diane L.; Dolle, Roland E. Journal of Medicinal Chemistry, 2009 , vol. 52, # 18 p. 5685 - 5702
  • Route3
    • null|null
      89166-80-3
    • ~%
    • In-stock
      5-Bromo-2-pyrimidinecarboxylic acid|CS-W008708
      37131-87-6

    References

    • Holland; Slack Chemistry and Industry (London, United Kingdom), 1954 , p. 1203

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   63.08
  • LogP   0.9373
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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