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Methyl 5-bromo-1H-pyrrole-3-carboxylate

  • CAS No. 16420-39-6

  • Cat. No. CS-W006282
  • Purity≥95%
  • MDL No.MFCD09841652

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

Methyl 5-bromo-1H-pyrrole-3-carboxylate|CS-W006282

Structure of 16420-39-6

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General Information

  • CAS No. 16420-39-6
  • Cat. No. CS-W006282
  • Purity ≥95%
  • MDL No. MFCD09841652
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO₂
  • Molecular Weight 204.02
  • Synonym(s) Methyl 5-Bromo-3-pyrrolecarboxylate
  • SMILES COC(=O)C1=CNC(Br)=C1

Description

Methyl 5-bromo-1H-pyrrole-3-carboxylate features a brominated pyrrole core with a methyl ester at the C3 position, enabling direct functionalization in cross-coupling reactions. The electron-deficient heterocycle integrates readily into complex scaffolds under standard conditions. This bench-stable reagent offers predictable regioselectivity and facilitates rapid diversification of bioactive molecules.

Application

Methyl 5-bromo-1H-pyrrole-3-carboxylate serves as a versatile building block for the synthesis of substituted pyrroles and heterocyclic scaffolds. The bromine at the 5-position enables palladium-catalyzed cross-coupling reactions, while the ester group facilitates further functionalization. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Takeda Pharmaceutical Company Limited Patent: US2007/60623 A1, 2007 ; Location in patent: Page/Page column 23 ;

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   42.09
  • LogP   1.5638
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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