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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

Comprehensive Guide to 4-Bromo-1H-Pyrazole-5-Carboxylic Acid (CAS No. 13745-17-0): Properties, Applications, and Industry Insights

4-Bromo-1H-pyrazole-5-carboxylic acid (CAS No. 13745-17-0) is a versatile heterocyclic compound widely recognized in pharmaceutical and agrochemical research. This brominated pyrazole derivative serves as a critical building block for synthesizing bioactive molecules, owing to its unique structural features. The compound's molecular formula, C₄H₃BrN₂O₂, combines a carboxylic acid functional group with a bromo-substituted pyrazole ring, enabling diverse chemical modifications.

Recent trends in drug discovery highlight the growing demand for pyrazole-based intermediates like 4-bromo-1H-pyrazole-5-carboxylic acid. Researchers frequently search for "pyrazole carboxylic acid derivatives" or "brominated heterocycles synthesis," reflecting its relevance in developing kinase inhibitors and antimicrobial agents. The compound's metal-chelating properties also make it valuable in materials science, particularly in designing luminescent sensors and catalysts.

From a synthetic chemistry perspective, CAS 13745-17-0 demonstrates remarkable reactivity in cross-coupling reactions. Its bromine atom at the 4-position facilitates Suzuki-Miyaura and Buchwald-Hartwig couplings, while the carboxyl group enables esterification or amide bond formation. This dual functionality explains why "4-bromo pyrazole building block" ranks high in organic chemistry literature searches. Recent studies (2022-2023) emphasize its role in creating EGFR tyrosine kinase inhibitors for targeted cancer therapies.

The compound's physicochemical properties warrant special attention. With a molecular weight of 190.98 g/mol and typically appearing as off-white crystalline powder, 4-bromo-1H-pyrazole-5-carboxylic acid exhibits moderate solubility in polar aprotic solvents like DMSO (≥50 mg/mL). Its stability under inert atmospheres and melting point range of 210-215°C make it suitable for high-temperature reactions. These characteristics address common search queries such as "pyrazole solubility data" and "thermal stability of bromo-carboxylic acids."

In agrochemical applications, this pyrazole derivative serves as precursor for herbicidal compounds. Patent analyses reveal its incorporation into protoporphyrinogen oxidase (PPO) inhibitors – a hot topic in sustainable weed control. The "4-position bromine substitution" enhances lipid solubility, improving plant membrane penetration. This aligns with industry demands for "eco-friendly crop protection chemicals" and "low-residue pesticides," as reflected in recent Google Scholar metrics.

Quality control protocols for CAS 13745-17-0 typically involve HPLC purity verification (>98%) and halogen content analysis. Advanced characterization techniques like ¹H/¹³C NMR and HRMS confirm the structure, addressing laboratory professionals' searches for "pyrazole characterization methods." Storage recommendations (2-8°C in amber vials) and handling precautions (use of nitrogen blankets) ensure long-term stability – key considerations for bulk purchasers.

Emerging applications in material science leverage the compound's ability to form coordination polymers. Its carboxylate moiety binds transition metals, creating porous frameworks for gas storage – a subject gaining traction in "MOF design" research. The bromine atom further enables post-synthetic modifications, making it valuable for creating functionalized materials with tunable porosity.

Market intelligence indicates rising global demand for 4-bromo-1H-pyrazole-5-carboxylic acid, particularly from contract research organizations (CROs). Price benchmarking data (2023) shows 10-15% annual growth for high-purity batches (>99%), driven by pharmaceutical R&D in Asia-Pacific regions. This correlates with increased searches for "pyrazole suppliers GMP-certified" and "custom synthesis bromo heterocycles."

Environmental and regulatory aspects of CAS 13745-17-0 remain favorable compared to heavier halogenated compounds. Its ready biodegradability (OECD 301D) and low bioaccumulation potential meet green chemistry principles, responding to queries about "sustainable brominated intermediates." Proper waste disposal involves neutralization followed by approved incineration – a protocol frequently searched by EHS managers.

Future research directions may explore enzymatic synthesis routes for 4-bromo-1H-pyrazole-5-carboxylic acid, addressing the biotech community's interest in "green synthesis pyrazoles." Computational studies predicting its metabolic pathways (via CYP450 enzymes) also represent an active area, particularly for drug metabolism researchers investigating "pyrazole pharmacokinetics."

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• 1092683-57-2(4-Bromo-1H-pyrazole-3-carboxylic acid)
• 6076-14-8(Ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate)
• 84547-86-4(4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid)
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• 1092683-01-6(3-Amino-4-bromo-1H-pyrazole-5-carboxylic acid)
• 1232838-31-1(Methyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate)
• 351990-74-4(5-amino-4-bromo-1H-pyrazole-3-carboxylic Acid)