Methyl 4-bromo-1H-pyrrole-2-carboxylate

Name: Methyl 4-bromo-1H-pyrrole-2-carboxylate
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CAS No. 934-05-4
Cat. No. CS-W007392
Purity≥95%
MDL No.MFCD00832855

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FedEx Limited Quantities Ground	$0.00
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Methyl 4-bromo-1H-pyrrole-2-carboxylate|CS-W007392

Structure of 934-05-4

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General Information

CAS No. 934-05-4
Cat. No. CS-W007392
Purity ≥95%
MDL No. MFCD00832855
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆BrNO₂
Molecular Weight 204.02
Synonym(s) Methyl 4-bromopyrrole-2-carboxylate
SMILES COC(C1=CC(Br)=CN1)=O

Description

Methyl 4-bromo-1H-pyrrole-2-carboxylate features a brominated pyrrole core with a methyl ester at the C2 position, enabling direct functionalization in cross-coupling and heterocyclic synthesis. The electron-deficient pyrrole ring facilitates palladium-catalyzed reactions, while the bench-stable ester group supports straightforward manipulation under standard conditions.

Application

Methyl 4-bromo-1H-pyrrole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-established bromine reactivity. The ester group provides compatibility with standard transformations, while the pyrrole core offers predictable regiochemistry and functional group tolerance. Its bench-stable nature and ease of purification make it ideal for constructing complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  1193-62-0
- ~87%
- In-stock
  
  934-05-4
- In-stock
  
  934-07-6
References
- Green Chemistry, , vol. 13, # 1 p. 102 - 108
Route2
- In-stock
  
  1193-62-0
- ~54%
- In-stock
  
  934-05-4
- In-stock
  
  934-07-6
- In-stock
  
  937-16-6
References
- Wischang, Diana; Radlow, Madlen; Hartung, Jens Dalton Transactions, 2013 , vol. 42, # 33 p. 11926 - 11940
Route3
- 67-56-1
- In-stock
  
  72652-32-5
- ~80%
- In-stock
  
  934-05-4
References
- Kitamura, Chitoshi; Yamashita, Yoshiro Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 10 p. 1443 - 1447

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 42.09
LogP 1.5638
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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Methyl 4-bromo-1H-pyrrole-2-carboxylate

CAS No. 934-05-4

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