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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acid esters

Comprehensive Overview of Ethyl 3-bromo-4-pentylbenzoate (CAS No. 1131594-50-7): Properties, Applications, and Industry Insights

Ethyl 3-bromo-4-pentylbenzoate (CAS No. 1131594-50-7) is a specialized organic compound gaining attention in pharmaceutical and material science research. This ester derivative, characterized by its brominated aromatic ring and pentyl side chain, exhibits unique physicochemical properties that make it valuable for synthetic applications. With a molecular formula of C₁₄H₁₉BrO₂, this compound has a molecular weight of 299.21 g/mol and typically appears as a pale-yellow to colorless liquid at room temperature.

The compound's structural features – particularly the electron-withdrawing bromo group at the 3-position and the lipophilic pentyl moiety at the 4-position – contribute to its reactivity in cross-coupling reactions. Recent studies highlight its potential as an intermediate in the synthesis of liquid crystal materials, aligning with the growing demand for advanced display technologies. Researchers are exploring its role in creating organic semiconductors, a hot topic in renewable energy and flexible electronics development.

From a synthetic chemistry perspective, Ethyl 3-bromo-4-pentylbenzoate serves as a versatile building block for palladium-catalyzed coupling reactions, including Suzuki-Miyaura and Heck reactions. Its ester functionality allows for further derivatization, making it valuable for structure-activity relationship studies in medicinal chemistry. The compound's stability under various conditions has prompted investigations into its use as a photoacid generator precursor in photoresist formulations, particularly relevant for semiconductor manufacturing processes.

Analytical characterization of CAS 1131594-50-7 typically involves GC-MS, HPLC, and ¹H/¹³C NMR spectroscopy. The bromine atom produces distinctive splitting patterns in NMR spectra, while mass spectrometry reveals characteristic fragmentation patterns. These analytical signatures are crucial for quality control in industrial applications, especially when the compound is used as a high-purity reference standard for analytical methods development.

Environmental and safety assessments of Ethyl 3-bromo-4-pentylbenzoate indicate it requires standard laboratory handling procedures. While not classified as highly hazardous, proper ventilation and personal protective equipment are recommended during manipulation. The compound's biodegradation potential and ecotoxicological profile are currently under investigation as part of the chemical industry's push toward greener alternatives.

Market trends show increasing demand for brominated aromatic compounds like 1131594-50-7, particularly in Asia-Pacific regions where electronic materials production is expanding. Patent analysis reveals growing intellectual property activity surrounding derivatives of this compound, especially for applications in organic light-emitting diodes (OLEDs) and photovoltaic materials. These developments align with global interest in sustainable energy solutions and advanced display technologies.

Future research directions for Ethyl 3-bromo-4-pentylbenzoate may explore its potential in metal-organic frameworks (MOFs) or as a precursor for biologically active molecules. The compound's balanced lipophilicity (LogP ≈ 4.2) makes it particularly interesting for drug discovery applications where membrane permeability is crucial. Recent publications have begun investigating its use in creating fluorescent probes for cellular imaging, tapping into the expanding field of chemical biology.

From a regulatory standpoint, CAS 1131594-50-7 currently falls under general chemical inventory listings without special restrictions. However, manufacturers and researchers should monitor evolving chemical regulations, particularly concerning brominated compounds and their environmental impact. Proper documentation of safety data sheets (SDS) and compliance with REACH regulations remains essential for commercial distribution.

In conclusion, Ethyl 3-bromo-4-pentylbenzoate represents an important synthetic intermediate with diverse applications across multiple high-tech industries. Its unique combination of aromatic bromination and ester functionality offers chemists valuable opportunities for molecular design and innovation. As research continues to uncover new applications, this compound is poised to play an increasingly significant role in advanced materials development and specialty chemical synthesis.

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