• 1. An eco-friendly biomass pretreatment strategy utilizing reusable enzyme mimicking nanoparticles for lignin depolymerization and biofuel production
  Rajiv Chandra Rajak,Pathikrit Saha,Mamata Singhvi,Darae Kwak,Danil Kim,Huijeong Lee,Aarti R. Deshmukh,Yingjie Bu,Beom Soo Kim Green Chem. 2021 23 5584

Comprehensive Analysis of 3-Bromo-5-ethoxy-4-hydroxybenzaldehyde (CAS No. 3111-37-3): Properties, Applications, and Industry Trends

3-Bromo-5-ethoxy-4-hydroxybenzaldehyde (CAS No. 3111-37-3) is a specialized organic compound that has garnered significant attention in pharmaceutical and agrochemical research. This brominated benzaldehyde derivative features a unique molecular structure, combining ethoxy and hydroxy functional groups, which contribute to its reactivity and versatility in synthetic chemistry. Researchers frequently explore its potential as a key intermediate in the synthesis of bioactive molecules, particularly in the development of antimicrobial agents and plant growth regulators.

The compound's CAS number 3111-37-3 serves as a critical identifier in global chemical databases, ensuring precise tracking in regulatory and safety documentation. Its molecular formula C9H9BrO3 and molecular weight 245.07 g/mol are frequently searched parameters in academic and industrial settings. Recent studies highlight its role in green chemistry applications, aligning with the growing demand for sustainable synthesis methods. The ethoxy group in particular enhances solubility in organic solvents, making it valuable for catalytic reactions and ligand design.

In the context of current research trends, 3-Bromo-5-ethoxy-4-hydroxybenzaldehyde is often discussed alongside structure-activity relationship (SAR) studies. Its electron-withdrawing bromo substituent influences electrophilic aromatic substitution patterns, a topic frequently queried in organic chemistry forums. Analytical techniques like HPLC purification and NMR characterization are essential for verifying its purity, as emphasized in recent peer-reviewed journals. The compound's stability under ambient storage conditions (typically 2-8°C) is another practical consideration for laboratory handling.

From an industrial perspective, the demand for halogenated benzaldehydes like 3111-37-3 has risen due to their utility in material science innovations. Patent literature reveals applications in photoactive polymers and liquid crystal displays, where its conjugated aromatic system contributes to desired optical properties. Environmental scientists also investigate its biodegradation pathways, responding to concerns about persistent organic pollutants – a hot-button issue in environmental chemistry circles.

The synthesis of 3-Bromo-5-ethoxy-4-hydroxybenzaldehyde typically involves regioselective bromination of phenolic precursors, a process optimized for atom economy in modern labs. Computational chemists employ DFT calculations to predict its reactivity, addressing common search queries about molecular orbital interactions. Its crystallographic data (space group P21/c) provides valuable insights for X-ray diffraction specialists, while the aldehyde carbonyl stretch at ~1680 cm?1 serves as a diagnostic IR fingerprint.

Quality control protocols for CAS 3111-37-3 emphasize residual solvent analysis and heavy metal screening, reflecting stringent ICH guidelines for pharmaceutical intermediates. The compound's logP value (~2.1) makes it a subject of interest in QSAR modeling for drug discovery. Recent breakthroughs in flow chemistry have enabled more efficient production scales, answering industry demands for process intensification solutions.

Emerging applications include its use as a fluorescence quencher in biochemical assays and as a cross-coupling partner in palladium-catalyzed reactions. The hydroxy-aldehyde motif allows for further functionalization through Schiff base formation, a feature exploited in coordination chemistry. Safety data sheets highlight standard precautions for laboratory handling, with particular attention to skin protection due to potential dermal sensitivity.

Market analysts note steady growth in the fine chemicals sector for compounds like 3-Bromo-5-ethoxy-4-hydroxybenzaldehyde, driven by custom synthesis services and contract research organizations. Academic purchasing trends show increased demand for small-scale quantities (100mg-5g) for method development studies. The compound's chromatographic behavior on reverse-phase columns is frequently documented to assist analytical chemists.

Future research directions may explore its potential in metal-organic frameworks (MOFs) or as a synthon for heterocyclic compounds. The ethoxy group's rotamer dynamics present interesting questions for molecular spectroscopy investigations. As regulatory landscapes evolve, documentation of REACH compliance for 3111-37-3 remains crucial for European market access.

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