950858-06-7

Usage

Uses

Used in Organic Synthesis:
2,6-Difluoro-4-iodophenol is used as a building block in organic synthesis for the creation of a variety of compounds. Its presence in the synthesis process can influence the reactivity and selectivity of the resulting products, making it a versatile component in the development of new chemical entities.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,6-Difluoro-4-iodophenol is utilized as a key intermediate in the synthesis of potential drug candidates. Its unique halogenated structure can contribute to the pharmacological properties of the final drug, such as enhancing solubility, bioavailability, or targeting specific biological receptors.
Used in Agrochemical Development:
2,6-Difluoro-4-iodophenol also finds applications in the agrochemical sector, where it may be used in the synthesis of new pesticides or herbicides. Its chemical properties can be harnessed to create compounds that are effective against pests or weeds while ensuring minimal environmental impact.
Used as a Reagent in Chemical Reactions:
2,6-DIFLUORO-4-IODOPHENOL serves as a reagent in chemical reactions, particularly for the formation of carbon-carbon and carbon-heteroatom bonds. Its reactivity and the ease with which it can participate in bond-forming reactions make it a valuable tool for chemists in various research and development settings.

InChI:InChI=1/C6H3F2IO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H

Upstream product

• 28177-48-2 2,6-difluorophenol 

Downstream Products

• 886762-68-1 2,6-difluoro-4-iodoanisole 

Relevant academic research and scientific papers

A Novel 18F-Labeled Radioligand for Positron Emission Tomography Imaging of 11β-Hydroxysteroid Dehydrogenase (11β-HSD1): Synthesis and Preliminary Evaluation in Nonhuman Primates

11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) catalyzes the conversion of cortisone to cortisol and controls a key pathway in the regulation of stress. Studies have implicated 11β-HSD1 in metabolic diseases including type 2 diabetes and obesity, as well as stress-related disorders and neurodegenerative diseases, such as depression and Alzheimer's disease (AD). We have previously developed [11C]AS2471907 as a PET radiotracer to image 11β-HSD1 in the brain of nonhuman primates and humans. However, the radiosynthesis of [11C]AS2471907 was unreliable and low-yielding. Here, we report the development of the 18F-labeled version [18F]AS2471907, including the synthesis of two iodonium ylide precursors and the optimization of 18F-radiosynthesis. Preliminary PET experiments, composed of a baseline scan of [18F]AS2471907 and a blocking scan with the reversible 11β-HSD1 inhibitor ASP3662 (0.3 mg/kg), was also conducted in a rhesus monkey to verify the pharmacokinetics of [18F]AS2471907 and its specific binding in the brain. The iodonium ylide precursors were prepared in a seven-step synthetic route with an optimized overall yield of 7sim;2%. [18F]AS2471907 was synthesized in good radiochemical purity, with the ortho regioisomer of iodonium ylide providing greater radiochemical yield as compared with the para regioisomer. In monkey brain, [18F]AS2471907 displayed high uptake and heterogeneous distribution, while administration of the 11β-HSD1 inhibitor ASP3662 significantly reduced radiotracer uptake, thus demonstrating the binding specificity of [18F]AS2471907. Given the longer half-life of F-18 and feasibility for central production and distribution, [18F]AS2471907 holds great promise to be a valuable PET radiotracer to image 11β-HSD1 in the brain.

Efficient and reliable iodination and o-Methylation of fluorinated phenols

Fluorinated phenols and other electron-deficient phenolic substrates are efficiently and cleanly iodinated by an iodine/ iodide mixture employing alkaline conditions. This protocol turned out to be the most practical for the generation of such highly fluorinated iodophenols. For later application in coupling processes the protection of the phenolic hydroxy moiety is often required. Therefore, a practical iodination and subsequent methylation sequence was elaborated providing the highly fluorinated anisoles with good to excellent yields. The developed method is applicable for a broad scope of fluorinated phenols and analogues.