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

Name: Ethyl 4-bromo-1H-pyrrole-2-carboxylate
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CAS No. 433267-55-1
Cat. No. CS-W009320
Purity≥97%
MDL No.MFCD06205071

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Ethyl 4-bromo-1H-pyrrole-2-carboxylate|CS-W009320

Structure of 433267-55-1

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General Information

CAS No. 433267-55-1
Cat. No. CS-W009320
Purity ≥97%
MDL No. MFCD06205071
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈BrNO₂
Molecular Weight 218.05
Synonym(s) Ethyl 4-bromopyrrole-2-carboxylate
SMILES O=C(C1=CC(Br)=CN1)OCC

Description

Ethyl 4-bromo-1H-pyrrole-2-carboxylate features a brominated pyrrole core with an ester-functionalized C2 position, enabling direct coupling in cross-coupling reactions. The electron-deficient pyrrole ring enhances reactivity in palladium-catalyzed transformations, while the ethyl ester group provides stability and solubility under standard conditions.

Application

Ethyl 4-bromo-1H-pyrrole-2-carboxylate serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions at the C4 position. The bromine substituent facilitates efficient functionalization under standard Suzuki, Stille, or Negishi conditions, while the pyrrole core provides access to biologically relevant scaffolds. Bench-stable and readily purified by flash chromatography, it functions effectively in multi-step syntheses requiring orthogonality and mild reaction conditions.

Synthesis

Route1
- In-stock
  
  2199-43-1
- ~52%
- In-stock
  
  433267-55-1
References
- Bergauer, Markus; Gmeiner, Peter Synthesis, 2002 , # 2 p. 274 - 278
Route2
- 516465-80-8
- ~99%
- In-stock
  
  433267-55-1
References
- Handy, Scott T.; Bregman, Howard; Lewis, Jennifer; Zhang, Xiaolei; Zhang, Yanan Tetrahedron Letters, 2003 , vol. 44, # 3 p. 427 - 430

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 42.09
LogP 1.9539
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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

CAS No. 433267-55-1

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