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CS-W001157 4
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Methyl 5-bromo-1H-pyrrole-2-carboxylate

  • CAS No. 934-07-6

  • Cat. No. CS-W006646
  • Purity≥95%
  • MDL No.MFCD09801030

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

Methyl 5-bromo-1H-pyrrole-2-carboxylate|CS-W006646

Structure of 934-07-6

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General Information

  • CAS No. 934-07-6
  • Cat. No. CS-W006646
  • Purity ≥95%
  • MDL No. MFCD09801030
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO₂
  • Molecular Weight 204.02
  • Synonym(s) None
  • SMILES COC(C(N1)=CC=C1Br)=O

Description

Methyl 5-bromo-1H-pyrrole-2-carboxylate features a brominated pyrrole core with a methyl ester at the C2 position, enabling direct functionalization in cross-coupling reactions. The electron-deficient pyrrole ring facilitates palladium-catalyzed transformations, while the bench-stable ester group supports straightforward derivatization. This compound serves as a key intermediate in synthesizing bioactive heterocycles and pharmaceutical scaffolds.

Application

Methyl 5-bromo-1H-pyrrole-2-carboxylate serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions at the C5 position. The bromine moiety exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the methyl ester group allows for selective reduction or hydrolysis. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for medicinal chemistry applications and modular scaffold construction.

Synthesis

  • Route1

    References

    • Trost, Barry M.; Dong, Guangbin Chemistry - A European Journal, 2009 , vol. 15, # 28 p. 6910 - 6919
  • Route2

    References

    • Green Chemistry, , vol. 13, # 1 p. 102 - 108
  • Route3

    References

    • Wischang, Diana; Radlow, Madlen; Hartung, Jens Dalton Transactions, 2013 , vol. 42, # 33 p. 11926 - 11940

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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