• 1. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
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• 2. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
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  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 4. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 5. Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography
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4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol (CAS No. 81233-93-4): A Versatile Fluorinated Building Block for Modern Organic Synthesis

In the rapidly evolving field of fluorinated organic compounds, 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol (CAS 81233-93-4) has emerged as a valuable synthetic intermediate with broad applications in pharmaceutical research, material science, and specialty chemicals. This fluorophenyl alkyne derivative combines the unique electronic properties of fluorine substitution with the versatile reactivity of an acetylenic alcohol, making it particularly attractive for contemporary drug discovery programs and advanced material development.

The molecular structure of 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol features three key functional elements: a para-fluorinated phenyl ring, a terminal alkyne moiety, and a tertiary propargylic alcohol. This combination creates multiple reactive sites that can participate in various transformations, including Sonogashira couplings, click chemistry reactions, and nucleophilic additions. The presence of fluorine at the para position significantly influences the compound's electronic properties, often enhancing metabolic stability when incorporated into bioactive molecules - a feature highly sought after in modern medicinal chemistry.

Recent trends in pharmaceutical research have shown growing interest in fluorine-containing building blocks like CAS 81233-93-4, driven by the need to develop more stable and bioavailable drug candidates. Approximately 30% of newly approved small-molecule drugs now contain fluorine atoms, reflecting the importance of compounds such as 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol in contemporary drug discovery. The compound serves as a precursor for various fluorinated heterocycles and has been utilized in the synthesis of potential kinase inhibitors and CNS-active molecules.

Beyond pharmaceutical applications, 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol finds use in material science as a monomer for specialty polymers. The fluorinated aromatic system contributes to thermal stability and chemical resistance, while the alkyne functionality enables polymerization through various mechanisms. Researchers have explored its incorporation into high-performance polymers for electronic applications, where the fluorine moiety helps tune dielectric properties and the acetylenic group facilitates cross-linking.

The synthetic utility of CAS 81233-93-4 extends to its role in click chemistry applications. The terminal alkyne can participate in copper-catalyzed azide-alkyne cycloadditions (CuAAC), allowing efficient conjugation with various azide-containing molecules. This property makes the compound valuable for bioconjugation strategies and the development of fluorescent probes or molecular imaging agents, particularly in the context of recent advances in bioorthogonal chemistry.

From a commercial perspective, the demand for fluorophenyl alkyne derivatives like 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol has grown steadily, reflecting broader market trends toward specialty fluorochemicals. Suppliers typically offer this compound with high purity (>97%) to meet the stringent requirements of pharmaceutical customers. Proper handling involves storage under inert atmosphere at low temperatures to maintain stability, though it remains relatively stable under standard laboratory conditions.

Environmental and regulatory considerations for 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol follow general guidelines for fluorinated organic compounds. While not classified as hazardous under current regulations, proper laboratory practices should be followed during handling. The compound's potential environmental impact appears limited based on its structural characteristics, though specific ecotoxicological data remains an area for further study as with many emerging fluorinated compounds.

Analytical characterization of CAS 81233-93-4 typically involves a combination of HPLC for purity assessment, NMR spectroscopy (particularly ¹⁹F NMR for the fluorine moiety), and mass spectrometry for structural confirmation. The compound shows characteristic signals in ¹H NMR around δ 7.4-7.6 ppm for the aromatic protons and δ 1.7 ppm for the methyl groups, with the alkyne proton appearing downfield. These analytical features facilitate quality control in both research and production settings.

Future research directions for 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol may explore its potential in catalysis and supramolecular chemistry, where the combination of fluorine substitution and alkyne functionality could enable novel applications. The growing interest in fluorine-specific interactions in molecular recognition processes suggests additional opportunities for this compound in chemical biology and materials design. As synthetic methodologies continue to advance, particularly in C-F bond activation and alkyne functionalization, the utility of this building block will likely expand further.

For researchers considering 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol for their projects, several practical considerations apply. The compound's solubility profile favors polar organic solvents like THF, DCM, and DMF, while showing limited water solubility. Standard purification techniques including column chromatography and recrystallization have proven effective. When planning synthetic routes, the tertiary alcohol moiety may require protection in some multi-step sequences, though it can also serve as a handle for further derivatization.

In conclusion, 4-(4-Fluorophenyl)-2-methylbut-3-yn-2-ol (CAS 81233-93-4) represents a versatile and increasingly important building block in modern organic synthesis. Its unique combination of fluorine substitution and alkyne functionality addresses multiple current needs in pharmaceutical research, materials science, and chemical biology. As the scientific community continues to explore the special properties of fluorinated compounds, this particular molecule stands poised to contribute to innovations across various chemistry-driven disciplines.

• 70250-73-6(3-Butyn-1-ol, 4-(4-fluorophenyl)-)
• 229015-32-1(3-Butyn-2-ol,4-(4-fluorophenyl)-)
• 229015-35-4(3-Butyn-2-ol,4-(4-fluorophenyl)-, (2S)-)
• 405065-71-6(3-Butyn-2-ol,4-(4-fluorophenyl)-,(2R)-(9CI))
• 1719-19-3(2-Methyl-4-phenylbut-3-yn-2-ol)
• 79756-91-5(2-Methyl-4-(p-tolyl)but-3-yn-2-ol)
• 486406-54-6(4-(3,5-Dimethylphenyl)-2-methylbut-3-yn-2-ol)
• 819861-95-5(3-Butyn-2-ol, 2-methyl-4-(2,3,4-trifluorophenyl)-)
• 647843-91-2(Cyclopentanol, 1-[(4-fluorophenyl)ethynyl]-)
• 63079-66-3(2-Methyl-4-(m-tolyl)but-3-yn-2-ol)