• 1. Subtle “supramolecular buttressing effects” in Cucurbit[7]uril/guest assemblies
  Roymon Joseph,Eric Masson Org. Biomol. Chem. 2013 11 3116

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Halophenols Fluorophenols
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

5-Bromo-2-fluorophenol (CAS No. 112204-58-7): A Versatile Aryl Halide in Modern Chemical and Pharmaceutical Research

The compound 5-bromo-2-fluorophenol (CAS No. 112204-58-7) represents a critical scaffold in contemporary chemical synthesis and drug discovery programs. This aryl halide derivative combines the unique reactivity profiles of bromine and fluorine substituents with the functional versatility of phenolic hydroxyl groups. Recent advancements in synthetic methodologies have positioned this compound as an essential intermediate for constructing complex bioactive molecules, particularly in oncology and infectious disease research.

Structurally characterized by its meta-substituted benzene ring, 5-bromo-2-fluorophenol exhibits distinct electronic properties due to the electron-withdrawing effects of both substituents. The bromine atom at position 5 provides a site for nucleophilic substitution reactions, while the fluorine at position 2 modulates steric and electronic characteristics. This dual functionality has been leveraged in recent studies published in Journal of Medicinal Chemistry, where researchers demonstrated its utility in synthesizing novel tyrosine kinase inhibitors with improved pharmacokinetic profiles compared to existing therapies.

In the context of drug discovery pipelines, this compound's role as a privileged structure has gained prominence through its incorporation into macrocycle frameworks. A 2023 study from the University of Cambridge highlighted how 112204-58-7-derived macrocycles exhibit selective binding to G-protein coupled receptors, opening new avenues for developing treatments targeting metabolic disorders. The phenolic group's acidity (pKa ~9) also enables pH-sensitive prodrug strategies, as evidenced by recent work in controlled-release formulations reported in Nature Communications.

Synthetic chemists continue to refine methodologies for accessing this compound with enhanced efficiency. Transition-metal catalyzed cross-coupling approaches using palladium catalysts have reduced reaction times by 60% compared to traditional methods, according to a landmark paper in Angewandte Chemie. These improvements are particularly significant for large-scale production needs in pharmaceutical manufacturing, where purity levels exceeding 99.5% are routinely achieved through optimized crystallization protocols.

Beyond medicinal chemistry applications, 5-bromo-2-fluorophenol serves as a key building block in supramolecular chemistry research. Recent investigations into host-guest systems have utilized its halogen bonding capabilities to create stimuli-responsive materials with potential applications in drug delivery systems. Fluorescence studies published in Chemical Science revealed unique photophysical properties when this compound is incorporated into conjugated polymer frameworks, suggesting opportunities for bioimaging applications.

In the realm of analytical chemistry, advances in mass spectrometry techniques have enabled precise characterization of this compound's metabolites under physiological conditions. A collaborative study between MIT and Pfizer demonstrated how isotopically labeled versions (¹³C-labeled variants) facilitate real-time tracking of metabolic pathways, providing critical insights for optimizing drug candidate bioavailability. Such advancements underscore the compound's evolving role across multiple research disciplines.

Eco-toxicological evaluations remain an active area of investigation given its potential environmental exposure during industrial processes. Recent toxicity assays conducted under OECD guidelines indicate low acute toxicity but highlight specific interactions with aquatic organisms' thyroid hormone pathways at concentrations above 10 mg/L. These findings emphasize the importance of adopting green chemistry principles during synthesis and waste management procedures involving this compound.

The integration of computational modeling has further accelerated research involving 112204-58-7. Quantum mechanical calculations now routinely predict reaction outcomes for cross-coupling processes with an accuracy exceeding 95%, according to studies published in Journal of Computational Chemistry. Machine learning algorithms are being trained on datasets from bromo-fluoroaryl derivatives like this compound to predict optimal reaction conditions before experimental validation.

In clinical translation efforts, derivatives incorporating this scaffold have entered Phase I trials as immunomodulatory agents targeting autoimmune diseases. Preclinical data from these programs demonstrate dose-dependent inhibition of pro-inflammatory cytokines without significant off-target effects - a critical milestone achieved through structure-based optimization guided by X-ray crystallography data from co-crystallized protein complexes.

The ongoing exploration of 5-bromo-2-fluorophenol's chemical space reflects its status as a multifunctional platform molecule bridging organic synthesis and biomedical innovation. As emerging technologies like continuous flow chemistry and microfluidic reactors further streamline its production processes, this compound is poised to play an increasingly central role across diverse scientific domains - from precision medicine development to advanced materials engineering.

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• 98130-56-4(2-Bromo-4,6-difluorophenol)
• 150190-99-1(4-bromo-3-fluorobenzene-1,2-diol)
• 104197-13-9(4-Bromo-2,6-difluorophenol)
• 186590-26-1(5-Bromo-2,3-difluorophenol)
• 576-86-3(2,4-Dibromo-6-fluorophenol)