5-Bromo-1H-pyrrole-2-carboxylic acid

Name: 5-Bromo-1H-pyrrole-2-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 28383-57-5
Cat. No. CS-W022299
Purity≥95%
MDL No.MFCD16996076

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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5-Bromo-1H-pyrrole-2-carboxylic acid|CS-W022299

Structure of 28383-57-5

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General Information

CAS No. 28383-57-5
Cat. No. CS-W022299
Purity ≥95%
MDL No. MFCD16996076
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄BrNO₂
Molecular Weight 189.99
Synonym(s) None
SMILES OC(C1=CC=C(N1)Br)=O

Description

5-Bromo-1H-pyrrole-2-carboxylic acid integrates a bromine substituent at the 5-position and a carboxylic acid group at the 2-position of the pyrrole ring. This configuration imparts enhanced electrophilicity and facilitates downstream functionalization via cross-coupling or derivatization. The compound exhibits good solubility in common organic solvents and stability under standard bench conditions, enabling efficient use in synthetic routes for bioactive heterocycles and pharmaceutical intermediates.

Application

5-Bromo-1H-pyrrole-2-carboxylic acid serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling direct functionalization at the C5 position via palladium-catalyzed cross-coupling reactions. The carboxylic acid group facilitates derivatization through amide formation or esterification, while the bromine atom provides orthogonal reactivity for further diversification. Bench-stable and compatible with standard purification methods, it functions reliably in the construction of complex pyrrole-based scaffolds used in agrochemical and pharmaceutical research.

Synthesis

Route1
- In-stock
  
  35302-72-8
- ~4%
- In-stock
  
  28383-57-5
- In-stock
  
  27746-02-7
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

Quality Control

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Computational Chemistry Data

TPSA 53.09
LogP 1.4754
H_Acceptors 1
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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5-Bromo-1H-pyrrole-2-carboxylic acid

CAS No. 28383-57-5

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