130995-12-9

Usage

Uses

Used in Pharmaceutical Industry:
(4-Fluorophenylethynyl)trimethylsilane is utilized as a synthetic building block for the creation of pharmaceuticals, leveraging its ability to modify the properties of organic molecules through the introduction of a fluorine atom. This modification can enhance the efficacy, selectivity, and pharmacokinetics of drug candidates.
Used in Agrochemical Industry:
In the agrochemical sector, (4-Fluorophenylethynyl)trimethylsilane serves as a key intermediate in the synthesis of agrochemicals, where the introduction of fluorine can improve the biological activity and environmental stability of the resulting compounds.
Used in Organometallic Chemistry:
(4-Fluorophenylethynyl)trimethylsilane is employed as an important reagent in organometallic chemistry, participating in a variety of synthetic reactions and functional group interconversions, which are crucial for the development of new chemical entities and materials.
Used in Chemical Research:
(4-FLUOROPHENYLETHYNYL)TRIMETHYLSILANE is also a valuable tool in chemical research, where it aids in exploring the effects of fluorination on molecular properties and reactivity, contributing to the advancement of synthetic methodologies and understanding of chemical behavior.

InChI:InChI=1/C11H13FSi/c1-13(2,3)9-8-10-4-6-11(12)7-5-10/h4-7H,1-3H3

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 1068-69-5 Tris(trimethylsilyl)methane 
• 1194-02-1 4-fluorobenzonitrile 
• 7681-65-4 copper(I) iodide 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 42122-44-1 methyl 3-(4-fluorophenyl)propiolate 
• 1209467-41-3 (S,E)-[1-(4-fluorobenzylidene)-2-phenyl-but-3-enyl]trimethylsilane 
• 1217677-77-4 (4-(4-fluorophenyl)but-1-en-3-yne-1,1,2-triyl)tribenzene 
• 1217677-82-1 4,4',4'',4'''-(but-1-en-3-yne-1,1,2,4-tetrayl)tetrakis(fluorobenzene) 
• 1007604-01-4 1-benzyl-4-(4-fluorophenyl)-1,2,3-triazole 
• 883793-48-4 2,5-bis(4-fluorophenyl)thiophene 
• 1358811-62-7 ethyl 5-(4-fluorophenyl)-3-(p-tolyl)thiophene-2-carboxylate 
• 1401250-43-8 C₁₄H₉F₂N₃ 
• 1401250-46-1 1,4-bis(4-fluorophenyl)-1H-1,2,3-triazole 
• 106492-30-2 (E)-1-fluoro-4-[2-(benzenesulfonyl)vinyl]benzene 
• 41024-58-2 1-(4-fluorophenyl)-2-(phenylsulfonyl)-1-ethanone 
• 1404226-36-3 C₁₄H₁₁FO₂S 
• 56759-24-1 (E)-1-fluoro-4-[2-(4-methylbenzene)sulfonylvinyl]benzene 
• 1404226-34-1 (Z)-1-(4-fluorostyrylsulfonyl)-4-methylbenzene 

Relevant academic research and scientific papers

Design of multilayered polymeric dielectric insulators for advanced microelectronics packaging

2,2-Bis[ 4-{ (4-fluorophenyl)buta-1,3-diynyl} phenyloxyphenyl] hexafluoropropane and co-polymer of 1,4-bis(4-fluorophenyl)buta-1,3-diyne and hexafluorobisphenol-A were prepared for the use as photosensitive multilayered polymeric dielectric insulators. Th

A new one-pot arylacetylene synthesis: 4-RC6H4C-≡C(TMS) from 4- RC6H4CN and LiC(TMS)3(THF)2 via Li[N(TMS)C(C6H4R-4)C(TMS)2](THF) (TMS = SiMe3, R = H, F, Br, OMe or Bu(t))

Treatment of LiC(TMS)3(THF)2 with the nitrile 4-RC6H4CN in Et2O at ambient temperature yields the new lithium 1-aza-allyl Li[N(TMS)C(C6H4R- 4)C(TMS)2](THF) which readily eliminates LiN(TMS)2 upon heating in refluxing benzene yielding the acetylene 4-RC6H4C≡C(TMS) in quantitative (TMS = SiMe3; R = H, Br, OMe or Bu(t)) or low (R = F) yield.

Alkyne oxidations by cis-dioxoruthenium(VI) complexes. A formal [3 + 2] cycloaddition reaction of alkynes with cis-[(Cn*)(CF3CO2)Ru(VI)O2]ClO4 (Cn* = 1,4,7-trimethyl-1,4,7-triazacyclononane)

cis-Dioxoruthenium(VI) complexes, [Cn*(CF3CO2)Ru(VI)O2]ClO4 (1) (Cn* = 1,4,7-trimethyl-1,4,7-triazacyclononane) and cis-[(Tet-Me6)Ru(VI)O2](ClO4)2 (2) (Tet-Me6 = N,N,N',N'-tetramethyl-3,6-dimethyl-3,6-diazaoctane-1,8-diamine), oxidize disubstituted alkynes to 1,2-diketones selectively in good to excellent yields under ambient conditions. The reactions proceed via the formation of dark blue [(Cn*)(CF3CO2)Ru(IV)OC2R1R2O]+ intermediates, which display a characteristic UV-visible absorption band at 550-680 nm. With bis(trimethylsilyl)acetylene as substrate and 1 as the oxidant, the intermediate was isolated and structurally characterized by X-ray crystallography as a [3 + 2] cycloadduct. The kinetics of the cycloaddition of 1 with various substituted trimethylsilylacetylenes has been studied by stopped-flow spectrophotometry. With the exception of bis(trimethylsilyl)acetylene, the second-order rate constants were found to vary over a range of less than an order of magnitude irrespective of a 2.3 eV change of the calculated I(p) of the alkynes; therefore, a rate-limiting single electron-transfer mechanism is unlikely. The participation of oxirene (oxene insertion) and metallaoxetene ([2 + 2] cycloaddition) intermediates appears to be implausible based on product analysis. A linear Hammett correlation was established using σ+ and σ(jj)(G) parameters for the cycloaddition of 1 with para-substituted aryl trimethylsilylacetylenes, and the rate-limiting vinyl radical intermediate formation is proposed.

Pseudo five-component synthesis of 3-(hetero)arylmethyl-2,5-di(hetero)-aryl-substituted thiophenes via sonogashira-glaser cyclization sequence

The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Oxidative Addition of Alkenyl and Alkynyl Iodides to a AuI Complex

The first isolated examples of intermolecular oxidative addition of alkenyl and alkynyl iodides to AuI are reported. Using a 5,5′-difluoro-2,2′-bipyridyl ligated complex, oxidative addition of geometrically defined alkenyl iodides occurs readily, reversibly and stereospecifically to give alkenyl-AuIII complexes. Conversely, reversible alkynyl iodide oxidative addition generates bimetallic complexes containing both AuIII and AuI centers. Stoichiometric studies show that both new initiation modes can form the basis for the development of C?C bond forming cross-couplings.