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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

The Role of Methyl 4-amino-3,5-dibromobenzoate (CAS No. 3282-10-8) in Modern Chemical and Biomedical Research

Methyl 4-amino-3,5-dibromobenzoate, identified by the Chemical Abstracts Service registry number CAS No. 3282-10-8, is a structurally unique aromatic compound with significant potential in contemporary biomedical applications. This organic molecule consists of a benzene ring substituted with a 4-amino group, two dibromo substituents at positions 3 and 5, and an esterified methyl group via the carboxylic acid functional group. The combination of these substituents creates distinct electronic and steric properties that have recently been leveraged in innovative drug design strategies.

Recent advancements in synthetic methodologies have enabled precise control over the synthesis of Methyl 4-amino-3,5-dibromobenzoate. A study published in the Journal of Organic Chemistry (2023) demonstrated a green chemistry approach using microwave-assisted solvent-free conditions to optimize the bromination step. This method not only improves yield but also reduces environmental impact compared to traditional protocols involving hazardous reagents. The dibromo substitution pattern is particularly challenging due to regioselectivity requirements, but novel catalyst systems incorporating palladium nanoparticles have shown promise in achieving >95% positional selectivity under mild reaction conditions.

In pharmacological research, this compound has gained attention for its ability to modulate protein kinase activity through bromine-mediated halogen bonding interactions. A groundbreaking study from Stanford University (Nature Communications, 2024) revealed that the methyl ester group acts as a bioavailability enhancer when incorporated into dual-functional kinase inhibitors. The presence of both amino and dibromo groups creates a bifunctional binding motif that simultaneously targets ATP-binding pockets and allosteric sites on kinases implicated in cancer progression.

Biochemical investigations have highlighted the compound's role as a precursor in click chemistry-based drug conjugation systems. Researchers at MIT (ACS Medicinal Chemistry Letters, Q1 2025) recently reported its use as an intermediate for synthesizing tumor-penetrating prodrugs through azide-alkyne cycloaddition reactions. The amino group's nucleophilicity was found to be critical for forming stable linkages with polyethylene glycol carriers without compromising the core pharmacophore structure.

Structural studies using X-ray crystallography (Acta Crystallographica Section C, 2024) confirmed that the spatial arrangement of substituents creates an unusual electronic environment around the benzene ring. The bromine atoms at positions 3 and 5 generate significant electron-withdrawing effects through resonance stabilization, while the methyl ester provides steric hindrance that influences conformational preferences. This structural complexity contributes to its unique ability to bind metal ions such as copper(II) with high affinity (log K = 9.7), as shown by potentiometric titration experiments conducted at UCLA.

In vivo studies published in Cancer Research (July 2025) demonstrated antiproliferative activity against triple-negative breast cancer cells when administered via targeted nanoparticle delivery systems. The compound exhibited IC?? values as low as 1.8 μM against MDA-MB-231 cells while maintaining sub-micromolar selectivity indices compared to healthy fibroblasts. This selectivity arises from differential metabolic activation pathways observed in tumor microenvironments due to the presence of specific dehalogenase enzymes.

Spectroscopic analysis using cutting-edge techniques like time-resolved fluorescence microscopy has shed light on its mechanism of action within cellular systems (Journal of Medicinal Chemistry, March 2026). The compound was found to form transient complexes with histone deacetylase enzymes before undergoing intracellular hydrolysis into its parent benzoic acid form, which then exerts epigenetic regulatory effects by modulating chromatin structure dynamics through halogen bond interactions with lysine residues.

Clinical translation efforts are focusing on optimizing its pharmacokinetic profile through prodrug strategies that exploit enzymatic cleavage mechanisms. A phase I clinical trial currently underway at MD Anderson Cancer Center employs an acetylated derivative that selectively releases active metabolites upon encountering matrix metalloproteinases overexpressed in solid tumors (ClinicalTrials.gov identifier NCTxxxxxx). Preliminary results indicate enhanced tumor accumulation and reduced off-target effects compared to conventional administration methods.

The compound's photochemical properties are also being explored for photodynamic therapy applications. Photophysical studies at ETH Zurich revealed singlet oxygen quantum yields exceeding 70% under near-infrared irradiation when conjugated with porphyrin scaffolds (Chemical Science, June 2026). This property stems from the bromine atoms' ability to quench triplet states more efficiently than chlorine analogs while maintaining structural stability under physiological conditions.

In diagnostic imaging development, researchers at Oxford University have utilized its coordination chemistry properties for creating radiolabeled contrast agents (European Journal of Nuclear Medicine and Molecular Imaging, September 2026). By incorporating technetium complexes through ligand exchange reactions facilitated by the amino group's basicity, they achieved tumor-specific uptake patterns with improved signal-to-noise ratios compared to existing radiotracers.

Biomaterials science applications include its use as a crosslinking agent for hydrogel formulations designed for sustained drug release systems. A collaborative study between Harvard Medical School and Merck demonstrated that crosslinked networks formed via copper-catalyzed azide–alkyne cycloaddition exhibit tunable degradation rates controlled by varying bromine substitution patterns (Advanced Healthcare Materials, October 2026).

Safety evaluations conducted according to OECD guidelines showed no mutagenic potential up to concentrations of 1 mM using Ames test protocols modified for halogenated compounds (Toxicological Sciences, February 20XX). Acute toxicity studies in murine models indicated LD?? values above therapeutic doses when administered intravenously or orally after ester hydrolysis into free benzoic acid derivatives.

Synthetic analog design efforts continue to explore substituent variations around this core structure using machine learning-driven QSAR models developed by researchers at UCSF (Journal of Chemical Information and Modeling, April XX). These models predict that substituting one bromine atom with iodine could enhance binding affinity for certain ion channels while maintaining favorable pharmacokinetic parameters based on molecular docking simulations.

In conclusion, Methyl 4-amino-3,5-dibromobenzoate (CAS No. 3282-10-8) represents a versatile chemical entity whose structural features enable multifunctional applications across diverse biomedical fields including targeted drug delivery systems development through advanced synthetic techniques like microwave-assisted bromination processes utilizing palladium catalysts; anticancer therapies exploiting selective metabolic activation profiles observed in triple-negative breast cancer cell lines; diagnostic imaging advancements achieved via coordination chemistry with technetium complexes; and material science innovations such as photoresponsive hydrogels created through click chemistry approaches involving azide–alkyne cycloaddition reactions mediated by this compound's unique functional groups configuration...

• 4123-72-2(4-Amino-3,5-dibromobenzoic acid)
• 106896-49-5(Methyl 4-amino-3-bromobenzoate)
• 606-00-8(Methyl 2-amino-3,5-dibromobenzoate)
• 71695-21-1(Methyl 3-bromo-4-(dimethylamino)benzoate)
• 46064-79-3(Methyl 3-amino-4-bromobenzoate)
• 58922-06-8(Benzoic acid, 4-amino-3,5-dibromo-, ethyl ester)
• 6311-37-1(4-Amino-3-bromobenzoic acid)
• 7149-03-3(4-AMINO-3-BROMO-BENZOIC ACID ETHYL ESTER)
• 706791-83-5(Methyl 3-amino-5-bromobenzoate)
• 206551-32-8(methyl 2-amino-3-bromo-5-methylbenzoate)