459-56-3 | 4-Fluorobenzyl alcohol

CAS:459-56-3 | 4-Fluorobenzyl alcohol,Description

Synthesis Analysis

The synthesis of 4-fluorobenzyl alcohol and its derivatives has been explored through various methodologies. One approach involves the use of protecting groups, such as the 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, which offers a novel benzyl ether-type protecting group for alcohols. This group is introduced via benzyl bromide and cleaved with tetrabutylammonium fluoride, showcasing its stability and compatibility with oxidizing conditions (Crich, Li, & Shirai, 2009).

Molecular Structure Analysis

The molecular structure of 4-fluorobenzyl alcohol has been investigated through various spectroscopic techniques. Studies involving microwave and UV excitation spectra have provided insights into the S(0) and S(1) structures of 4-fluorobenzyl alcohol, revealing its gauche structure in both electronic states and the barriers to torsional motion of the attached -CH2OH group (Bird, Nikolaev, & Pratt, 2011).

Chemical Reactions and Properties

4-Fluorobenzyl alcohol participates in various chemical reactions, one of which involves its conversion to 4-[18F]fluorobenzyl halides, a process suitable for automated preparation and important for the synthesis of radiotracers (Iwata et al., 2000). Another study highlights its metabolic fate in rats, where major metabolites detected were glycine conjugates of the corresponding benzoic acids, indicating the metabolic pathways it undergoes (Blackledge, Nicholson, & Wilson, 2003).

Physical Properties Analysis

The physical properties of 4-fluorobenzyl alcohol, such as its rotational and electronic spectra, have been detailed, providing insights into its gauche structure and the dynamics of the attached -CH2OH group. The detailed analysis of these spectra helps in understanding the physical characteristics of this compound under various conditions (Bird, Nikolaev, & Pratt, 2011).

Chemical Properties Analysis

The chemical properties of 4-fluorobenzyl alcohol include its reactivity in forming derivatives and participating in oxidation reactions. For instance, N-Methylbenzylammonium fluorochromate(VI) on silica gel has shown selectivity in the oxidation of aryl alcohols to their corresponding aldehydes and ketones under mild conditions, demonstrating the versatile chemical behavior of 4-fluorobenzyl alcohol and its derivatives (Kassaee, Sayyed-alangi, & Sajjadi-Ghotbabadi, 2004).

Scientific Research Applications

• Alcohol Protecting Group : The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, related to 4FBA, serves as a novel alcohol protecting group, useful for direct stereocontrolled synthesis of beta (Crich, Li, & Shirai, 2009).
• Single-Molecule Fluorescence Imaging : A combination of compounds including 4-nitrobenzyl alcohol, closely related to 4FBA, reduces blinking and photobleaching in single-molecule fluorescence imaging (Dave, Terry, Munro, & Blanchard, 2009).
• Sedative-Hypnotic Activities : Derivatives of 4-hydroxybenzyl alcohol, structurally similar to 4FBA, demonstrate strong sedative-hypnotic activity, potentially offering new treatments for insomnia (Zhu et al., 2018).
• Synthesis of Fluorobenzyl Ethers : The reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane can synthesize various 4-[18F]fluoro-benzyl ethers, which are useful in radiochemical applications (Funke et al., 2006 ).
• Structural and Spectroscopic Analysis : 4FBA exhibits a gauche structure in electronic states, with tunneling motions affecting its microwave and UV spectra (Bird, Nikolaev, & Pratt, 2011).
• Metabolism Study : In rats, 4FBA is primarily metabolized to glycine conjugates of benzoic acids, with minor N-acetylcysteinyl conjugates also present in urine (Blackledge, Nicholson, & Wilson, 2003).
• Synthesis of Phosphopeptides : A study suggests that 4-bromobenzyl phosphoramidite is more efficient and stable compared to 4-fluorobenzyl groups for synthesizing Ser(P)-containing peptides (Perich & Johns, 1991).
• Production of Fluorinated Compounds : Oxidation of p-fluorobenzyl alcohol can produce p-fluorobenzaldehyde and p-fluorobenzoic acid, with potential applications in various chemical processes (Conte et al., 1998).
• Enhancement of Photostability : Conjugating compounds like 4-nitrobenzyl alcohol with cyanine fluorophore Cy5 enhances its photostability without altering its spectral characteristics (Altman et al., 2011).
• Synthesis of Fluorobenzyl Halides : A new method enables efficient preparation of 4-[18F]fluorobenzyl halides, useful in radiopharmaceutical applications (Iwata et al., 2000).
• Molecular Adsorption Studies : The thermogravimetry of cholic acid inclusion complexes with fluorobenzyl alcohols reveals insights into molecular adsorption on crystal surfaces (Shibakami et al., 1996).
• Anticancer Activity : Fluorine compounds with isoxazolylamino and phosphonate groups, possibly including 4FBA derivatives, show moderate anticancer activity in vitro (Song et al., 2005).
• Conformational Energy Predictions : Ab initio molecular orbital calculations for compounds like 2'-fluorobenzyl alcohol provide insights into their conformational energies (Schaefer & Parr, 1976).
• Neuroprotective Effects : 4-Hydroxybenzyl alcohol has shown neuroprotective effects in the postischemic brain, indicating potential medical applications (Luo et al., 2018).
• Tumor Angiogenesis Inhibition : 4-Hydroxybenzyl alcohol is a potential inhibitor of tumor angiogenesis and growth, suggesting its use in cancer therapy (Laschke et al., 2013).
• Eco-Friendly Synthesis : Biotransformation using Baker's yeast can efficiently synthesize aromatic alcohols like 4FBA with environmentally friendly properties (Saharan & Joshi, 2016).
• Aromatic Stacking in Catalysis : Aromatic stacking interactions, which can be affected by substituents in compounds like 4FBA, are crucial in catalysis involving aryl-alcohol oxidase (Ferreira et al., 2015 ).

Safety And Hazards

4-Fluorobenzyl alcohol is classified as a combustible liquid. It is advised to keep it away from heat, sparks, open flames, and hot surfaces. It should be handled with protective gloves, clothing, and eye/face protection. In case of fire, dry sand, dry chemical, or alcohol-resistant foam should be used for extinction.

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