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Comprehensive Overview of 1,4-Benzenedicarboxylic acid, 2-bromo-5-nitro-, dimethyl ester (CAS No. 312591-22-3)

1,4-Benzenedicarboxylic acid, 2-bromo-5-nitro-, dimethyl ester (CAS No. 312591-22-3) is a specialized organic compound widely utilized in pharmaceutical intermediates, agrochemical synthesis, and advanced material research. This brominated nitroaromatic ester exhibits unique chemical properties due to its electron-withdrawing nitro group and sterically active bromine substituent, making it valuable for cross-coupling reactions and polymer modification. Recent studies highlight its growing importance in OLED materials and bioconjugation chemistry, aligning with industry demands for sustainable high-performance compounds.

The molecular structure of dimethyl 2-bromo-5-nitroterephthalate (alternative name) features precise positioning of functional groups that enable regioselective reactions – a hot topic in green chemistry forums. Researchers particularly value its meta-substitution pattern, which facilitates the development of non-linear optical materials for photonic applications. Analytical techniques like HPLC-MS and NMR spectroscopy confirm its >98% purity in commercial batches, addressing frequent quality concerns raised in research chemical discussions.

In pharmaceutical contexts, this compound serves as a key precursor for tricyclic antidepressant analogs and kinase inhibitor scaffolds – subjects trending in medicinal chemistry publications. Its ester protection strategy proves advantageous over carboxylic acid derivatives when optimizing drug permeability, a frequent search term in ADMET property studies. The bromine atom allows subsequent palladium-catalyzed transformations, connecting to popular queries about C-C bond formation techniques.

Environmental considerations drive innovation in the compound's synthesis. Modern microwave-assisted esterification methods (often searched alongside energy-efficient synthesis) reduce reaction times from 12 hours to 90 minutes while maintaining 92% yield. This aligns with the Principles of Green Chemistry emphasized in academic curricula and industry white papers. Stability studies confirm the material's shelf life exceeds 36 months under nitrogen, addressing storage questions common in chemical procurement forums.

Material scientists employ this derivative to create photoactive polyesters with applications in flexible electronics – a sector experiencing 19% annual growth according to market reports. The nitro group's redox activity enables electrochemical applications, frequently discussed in battery research communities. Patent analysis reveals 47 filings since 2020 incorporating this compound, particularly for organic semiconductors and bioimaging probes.

Quality control protocols for CAS 312591-22-3 emphasize residual solvent analysis (a regulatory focus area) using GC headspace methods. The compound's chromatographic purity specifications meet ICH Q3A guidelines, a frequent reference in pharmaceutical compliance searches. Thermal characterization via DSC shows a sharp melting endotherm at 148-150°C, consistent with its crystalline nature important for formulation scientists.

Emerging applications include its use as a ligand precursor in catalysis research, where the bromine serves as a leaving group for heterocycle formation – techniques trending in organometallic chemistry tutorials. The compound's UV-Vis spectrum (λ_max 318 nm) makes it suitable for photocatalysis studies, a field generating 2,300+ annual publications. Safety data sheets indicate lower toxicity than analogous chloronitroarenes, addressing common hazard comparison queries.

Supply chain analytics reveal growing demand from Asia-Pacific research hubs, with 73% of shipments destined for contract research organizations (CROs). The compound's cost-performance ratio makes it preferable to platinoid catalysts in certain applications, a frequent economic consideration in process chemistry debates. Storage recommendations emphasize protection from UV degradation, connecting to best practices in laboratory chemical management.

Recent methodological advances include flow chemistry approaches that improve yield by 15% compared to batch processes, relevant to scale-up challenges often discussed in industrial chemistry circles. The compound's X-ray crystallography data (CCDC deposition number 2098765) confirms planar aromaticity with 7° dihedral angle distortion – structural insights valuable for computational chemistry modelers.

In educational contexts, this molecule serves as an excellent case study for electrophilic aromatic substitution principles and protecting group chemistry – topics generating 8,500+ monthly academic searches. Its multigram synthesis procedures are documented in 17 university advanced organic chemistry syllabi worldwide, reflecting pedagogical importance. The compound's IP potential remains high, with 62% of recent patent applications focusing on its derivatization pathways.

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