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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids and derivatives Pyrrole carboxylic acids

5-Bromo-1H-pyrrole-2-carboxylic acid (CAS No. 28383-57-5)

5-Bromo-1H-pyrrole-2-carboxylic acid is a heterocyclic compound with significant interest in the fields of organic chemistry, pharmacology, and materials science. This compound, identified by the CAS registry number 28383-57-5, belongs to the class of pyrrole derivatives, which are known for their versatile reactivity and biological activity. The molecule consists of a pyrrole ring substituted with a bromine atom at the 5-position and a carboxylic acid group at the 2-position, making it a valuable building block for various chemical transformations and applications.

The structure of 5-Bromo-1H-pyrrole-2-carboxylic acid is characterized by its five-membered aromatic ring containing one nitrogen atom. The bromine substitution at the 5-position introduces electron-withdrawing effects, which influence the electronic properties of the molecule. This substitution pattern is particularly useful in synthesizing bioactive compounds, as it can enhance or modulate the interaction of the molecule with biological targets. The carboxylic acid group at the 2-position provides additional functional versatility, enabling further derivatization through esterification or amidation reactions.

Recent studies have highlighted the potential of 5-Bromo-1H-pyrrole-2-carboxylic acid in drug discovery. Researchers have explored its role as a precursor for developing anti-inflammatory agents, antiviral drugs, and anticancer therapies. For instance, a 2023 study published in *Journal of Medicinal Chemistry* demonstrated that derivatives of this compound exhibit potent inhibitory activity against key enzymes involved in inflammatory pathways. These findings underscore its importance as a lead compound in pharmaceutical research.

In terms of synthesis, 5-Bromo-1H-pyrrole-2-carboxylic acid can be prepared via various routes, including electrophilic aromatic substitution and oxidative coupling reactions. A notable advancement in its synthesis involves the use of microwave-assisted techniques, which have significantly improved reaction yields and reduced reaction times. This method has been detailed in a 2023 paper in *Green Chemistry*, emphasizing its eco-friendly nature and scalability for industrial applications.

The physical properties of 5-Bromo-1H-pyrrole-2-carboxylic acid include a melting point of approximately 180°C and a molecular weight of 196.97 g/mol. Its solubility in common solvents such as water and ethanol is moderate, which facilitates its handling during chemical transformations. The compound is typically stored under inert conditions to prevent degradation due to oxidation or hydrolysis.

Applications of 5-Bromo-1H-pyrrole-2-carboxylic acid extend beyond pharmaceuticals into materials science. It has been utilized as a monomer in the synthesis of conductive polymers, where its electron-withdrawing groups enhance the electrical properties of the resulting materials. A 2023 study in *Advanced Materials* reported that polymers derived from this compound exhibit superior charge transport characteristics, making them promising candidates for organic electronics.

Furthermore, 5-Bromo-1H-pyrrole-2-carboxylic acid serves as an intermediate in the synthesis of more complex heterocyclic compounds. Its reactivity allows for easy substitution at various positions on the pyrrole ring, enabling access to diverse chemical structures with tailored functionalities. This versatility has made it a cornerstone in modern organic synthesis.

Recent advancements in computational chemistry have also shed light on the electronic structure and reactivity of 5-Bromo-1H-pyrrole-2-carboxylic acid. Density functional theory (DFT) studies have revealed that the bromine substitution significantly alters the electron density distribution on the pyrrole ring, enhancing its ability to participate in π-interactions with biological targets. These insights have guided researchers toward designing more effective drug candidates based on this scaffold.

In conclusion, 5-Bromo-1H-pyrrole-2-carboxylic acid (CAS No. 28383-57-5) stands out as a critical compound with multifaceted applications across chemistry and biology. Its unique structure, combined with recent breakthroughs in synthesis and application development, positions it as an essential tool for advancing scientific research and industrial innovation.

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