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CS-W001157 4
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4-Bromo-1H-pyrrole-2-carboxylic acid

  • CAS No. 27746-02-7

  • Cat. No. CS-D0459
  • Purity≥95%
  • MDL No.MFCD00832862

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

4-Bromo-1H-pyrrole-2-carboxylic acid|CS-D0459

Structure of 27746-02-7

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General Information

  • CAS No. 27746-02-7
  • Cat. No. CS-D0459
  • Purity ≥95%
  • MDL No. MFCD00832862
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrNO₂
  • Molecular Weight 189.99
  • Synonym(s) 4-BROMOPYRROLE-2-CARBOXYLIC ACID
  • SMILES O=C(C1=CC(Br)=CN1)O

Description

4-Bromo-1H-pyrrole-2-carboxylic acid integrates a bromine substituent at the C4 position of the pyrrole ring, delivering enhanced electrophilic reactivity and stability under standard conditions. The carboxylic acid group enables direct coupling reactions or derivatization, facilitating access to diverse heterocyclic scaffolds in medicinal chemistry and materials science applications.

Application

4-Bromo-1H-pyrrole-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling direct incorporation into biologically active heterocycles. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, while the carboxylic acid group supports amide formation and derivatization. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it well-suited for iterative synthesis of complex scaffolds.

Synthesis

  • Route1

    References

    • ADDEX PHARMACEUTICALS SA Patent: WO2006/123257 A2, 2006 ; Location in patent: Page/Page column 63 ; WO 2006/123257 A2
  • Route2

    References

    • Clark, Benjamin R.; O'Connor, Stephen; Fox, Deirdre; Leroy, Jacques; Murphy, Cormac D. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 18 p. 6306 - 6311

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   53.09
  • LogP   1.4754
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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