Molecular Formula: C17H16ClIO2
Molecular Weight: 414.66
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*The following content is generated by AI and is for reference only.
The chemical compound designated as (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran is a sophisticated organic intermediate widely utilized in modern medicinal chemistry and pharmaceutical research. While specific commercial databases may vary slightly regarding its exact CAS registry number due to the niche nature of specialized synthesis intermediates, this molecule is structurally characterized by a chiral tetrahydrofuran ring linked via an ether bond to a biphenyl-like system bearing distinct halogen substituents. The presence of the iodine atom at the 5-position of the phenyl ring and the chlorine at the 2-position renders this compound particularly valuable for cross-coupling reactions, such as Suzuki-Miyaura or Sonogashira couplings, which are pivotal in constructing complex biaryl scaffolds found in numerous bioactive agents.
The stereochemistry defined by the "(3S)" configuration indicates that this product possesses a specific optical activity, making it essential for applications where enantiomeric purity is critical for biological efficacy and safety. In drug discovery pipelines, such halogenated aryl ethers often serve as key building blocks for synthesizing kinase inhibitors, anti-inflammatory drugs, or compounds targeting the central nervous system. The iodine substituent acts as a versatile handle for further functionalization, allowing chemists to introduce diverse moieties to optimize pharmacokinetic properties like metabolic stability and receptor binding affinity. Furthermore, the tetrahydrofuran moiety provides structural rigidity and lipophilicity, which can enhance membrane permeability in potential therapeutic candidates.
This reagent is primarily employed in academic laboratories and industrial R&D facilities rather than as a final consumer product. Its usage requires strict adherence to safety protocols due to the potential toxicity associated with heavy halogens and organic solvents. Researchers utilize high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy to verify the purity and stereochemical integrity of the material before incorporation into multi-step synthetic routes. As the demand for precision medicine grows, the role of such highly functionalized, chiral intermediates becomes increasingly significant in accelerating the development of next-generation therapeutics with improved selectivity and reduced side effects.