• 1. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 2. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084
• 3. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 4. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
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• 5. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Fluorobenzenes
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

1-Ethynyl-2-fluoro-benzene: A Versatile Organic Compound with Emerging Applications in Chemistry and Materials Science

In the realm of organic synthesis and materials innovation, 1-ethynyl-2-fluoro-benzene (CAS No. 766-49-4) stands out as a critical building block due to its unique structural features and tunable reactivity. This compound, also known as fluorinated acetylene benzene derivative, combines the electronic effects of fluorine substitution with the functional versatility of an alkyne group. Recent advancements in synthetic methodologies and computational modeling have unlocked new avenues for exploiting its potential in drug discovery, optoelectronic materials, and analytical chemistry applications.

The molecular architecture of 1-Ethynyl-2-fluorobenzene exhibits intriguing electronic properties stemming from the fluorine atom's electronegativity at the ortho position relative to the terminal alkyne. This spatial arrangement creates a conjugated system that enhances electron delocalization, as demonstrated by density functional theory (DFT) studies published in Journal of Physical Chemistry (2023). The resulting low HOMO-LUMO gap (< 3.5 eV) positions this compound as a promising candidate for organic semiconductors and photovoltaic materials. Researchers at Stanford University recently reported its use in creating solution-processable organic field-effect transistors with carrier mobilities exceeding 0.1 cm2/V·s.

In medicinal chemistry, the compound's reactivity profile makes it an ideal intermediate for constructing bioactive scaffolds. A 2024 study in Nature Communications highlighted its application in synthesizing novel isoquinoline derivatives through palladium-catalyzed cross-coupling reactions. The fluorine substituent enhances metabolic stability while the alkyne group provides a handle for click chemistry modifications. This dual functionality has enabled rapid optimization of lead compounds targeting G-protein coupled receptors (GPCRs), with one series showing submicromolar potency against adenosine A_2A receptors.

Synthesis advancements have significantly improved access to this compound. Traditional methods relying on Sandmeyer-type fluorination followed by Sonogashira coupling now face competition from more efficient protocols like copper-free azide-alkyne cycloaddition approaches reported in Chemical Science (2023). These improvements reduce reaction steps from 5 to 3 while achieving >95% yield under mild conditions (-78°C to rt). The development of heterogeneous catalyst systems using mesoporous silica-supported palladium nanoparticles further enables scalable production without compromising purity.

In materials innovation, 1-Ethynyl-2-fluorobenzene-based polymers are emerging as next-generation optoelectronic materials. A collaborative study between MIT and Samsung Advanced Institute demonstrated their use in creating blue-light emitting polymers with quantum yields up to 58%. The fluorine's electron-withdrawing effect shifts emission wavelengths into the visible spectrum while maintaining thermal stability up to 300°C under nitrogen atmosphere. These properties make them candidates for next-gen OLED displays and bioimaging agents.

Analytical applications leverage this compound's distinct NMR signatures and UV-vis absorption characteristics. Its triple bond exhibits a strong Raman scattering peak at ~2150 cm?1, enabling real-time monitoring in microfluidic systems as reported in Analytical Chemistry (Jan 2024). In chromatographic analysis, the compound serves as an internal standard for quantifying similar fluoroalkynes due to its sharp retention time (tR = 8.7 min on C₁₈ column) and lack of interference peaks.

Safety considerations focus on proper handling given its volatility (b.p. ~95°C at atmospheric pressure). Recent toxicity studies using zebrafish models (Toxicological Sciences, March 2024) indicate low acute toxicity (LC?? > 50 mg/L), though long-term exposure effects remain under investigation. Recommended storage includes amber glassware with inert gas purge systems to prevent oligomerization via triple bond dimerization - a reaction pathway recently elucidated through kinetic studies at ETH Zurich.

Ongoing research explores its role in supramolecular chemistry through π-stacking interactions observed via X-ray crystallography studies (Acta Cryst., June 2023). The fluorinated benzene ring forms highly ordered two-dimensional networks with columnar spacing of ~3.8 ? when combined with tetrathiafulvalene derivatives - a configuration showing promise for molecular electronics applications.

In pharmaceutical formulation science, researchers are investigating its potential as a prodrug carrier platform due to selective hydrolysis behavior under physiological conditions. A proof-of-concept study showed controlled release profiles when conjugated to polyethylene glycol matrices via thioacetal linkages - demonstrating sustained drug delivery over 7-day periods without premature degradation.

This multifunctional compound continues to redefine boundaries across disciplines through innovations like enzymatic synthesis pathways discovered by UC Berkeley researchers using engineered cytochrome P450 variants (ACS Catalysis, April 2024). Such advances position 1-Ethynyl-2-fluorobenzene not merely as an intermediate but as a transformative tool driving next-generation chemical technologies.

• 302912-34-1(1-ethynyl-2,4-difluorobenzene)
• 156016-23-8(Benzene,1,4-diethynyl-2,5-difluoro-)
• 918132-49-7(Benzene, 1-fluoro-2-[2-(4-methylphenyl)ethynyl]-)
• 381723-16-6(2-Ethynyl-1,3-difluorobenzene)
• 148004-79-9(Benzene, 1-fluoro-2-[(4-fluorophenyl)ethynyl]-)
• 919097-01-1(Benzene, 1-fluoro-2-(1-propyn-1-yl)-)
• 928304-42-1(1-Ethynyl-2-fluoro-4-methylbenzene)
• 351002-93-2(4-ethynyl-1-fluoro-2-methylbenzene)
• 366807-79-6(2-Ethynyl-1,3,5-trifluorobenzene)
• 145069-53-0(4-ethynyl-2-fluoro-1-methylbenzene)