Production Method 1

70951-96-1

84547-93-3

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Sodium dichromate Solvents: Water ;  60 - 65 °C; 8 h, 60 - 65 °C

Reference

Nitropyrazoles 18. Synthesis and transformations of 5-amino-3,4-dinitropyrazole

Dalinger, I. L.; et al, Russian Chemical Bulletin, 2010, 59(8), 1631-1638

4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid Raw materials

• 4-Bromo-3-methyl-5-nitro-1H-pyrazole

4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid Preparation Products

• 4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid (84547-93-3)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazole carboxylic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Pyrazole carboxylic acids and derivatives

4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid (CAS No. 84547-93-3): A Versatile Intermediate in Modern Pharmaceutical and Chemical Research

4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid, identified by its CAS number 84547-93-3, is a significant compound in the realm of pharmaceutical and chemical synthesis. This heterocyclic aromatic carboxylic acid derivative has garnered considerable attention due to its versatile structural framework, which makes it a valuable intermediate in the development of various bioactive molecules. The presence of both bromo and nitro substituents on the pyrazole ring endows this compound with unique reactivity, enabling its application in diverse synthetic pathways.

The< strong>pyrazole core is a prominent scaffold in medicinal chemistry, known for its broad spectrum of biological activities. Pyrazole derivatives have been extensively studied for their potential as antimicrobial, anti-inflammatory, anticancer, and anti-viral agents. Among these derivatives, 4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid stands out due to its ability to serve as a precursor for more complex structures. The bromo and nitro groups facilitate further functionalization through nucleophilic substitution and reduction reactions, respectively, making it an indispensable building block in synthetic organic chemistry.

In recent years, there has been a surge in research focusing on the development of novel therapeutic agents derived from< strong>pyrazole-based compounds. The< strong>1H-pyrazole-3-carboxylic acid moiety is particularly noteworthy for its role in constructing pharmacophores that interact with biological targets. For instance, studies have demonstrated the efficacy of pyrazole derivatives in inhibiting enzymes such as dihydrofolate reductase (DHFR) and tyrosine kinases, which are crucial in cancer therapy. The incorporation of< strong>bromo and< strong>nitro substituents into these structures enhances their binding affinity and selectivity, thereby improving their therapeutic potential.

The< strong>nitro group in< strong>4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid is particularly noteworthy for its dual functionality. On one hand, it can be reduced to an amine group, introducing a new site for further chemical modification. On the other hand, the nitro group can participate in electrophilic aromatic substitution reactions, allowing for the introduction of additional substituents at specific positions on the pyrazole ring. This reactivity has been exploited in the synthesis of more complex heterocyclic systems, where precise control over substitution patterns is essential.

The< strong>bromo substituent provides another layer of functionalization potential. Bromine is a versatile electrophile that can undergo cross-coupling reactions with various nucleophiles, including organometallic reagents and transition metal catalysts. These reactions are widely used in pharmaceutical synthesis to construct carbon-carbon bonds and introduce diverse functional groups into organic molecules. For example, palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Heck couplings have been employed to incorporate aryl or vinyl groups into the< strong>pyrazole scaffold, expanding the structural diversity of derived compounds.

In the context of drug discovery, 4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid has been utilized as a key intermediate in the synthesis of novel antiviral agents. Recent studies have highlighted its role in developing inhibitors targeting viral proteases and polymerases. The ability to modify both bromo and nitro groups allows for fine-tuning of physicochemical properties such as solubility, permeability, and metabolic stability, which are critical factors in drug design. Additionally, computational modeling studies have suggested that pyrazole derivatives with such substituents exhibit favorable interactions with biological targets, reinforcing their potential as therapeutic candidates.

The synthetic utility of< strong>4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid extends beyond pharmaceutical applications. It has also found use in materials science and agrochemical research. For instance, pyrazole derivatives have been explored as ligands in coordination chemistry, where they form stable complexes with metal ions. These complexes exhibit interesting catalytic properties and have been investigated for their potential use in industrial processes. Moreover, some pyrazole-based compounds have shown promise as herbicides and fungicides due to their ability to disrupt essential biological pathways in plants.

The< strong>CAS No. 84547-93-3 designation ensures that researchers can reliably source this compound for their experiments while adhering to regulatory standards. The availability of high-purity< strong>4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid from reputable suppliers is crucial for ensuring reproducibility and consistency in research outcomes. As synthetic methodologies continue to evolve, this compound will likely remain a cornerstone in the development of innovative chemical entities.

In conclusion,< strong>4-Bromo-5-nitro-1H-pyrazole-3-carboxylic acid, with its CAS number 84547-93-3, represents a cornerstone compound in modern pharmaceutical and chemical research. Its unique structural features—specifically the presence of bromo and nitro substituents—make it an exceptionally versatile intermediate for constructing bioactive molecules. The ongoing exploration of its synthetic potential continues to yield novel applications across various scientific disciplines, underscoring its importance as a building block for future advancements.

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