40230-95-3

Usage

Uses

Used in Organic Synthesis:
1-((TRIMETHYLSILYL)ETHYNYL)-4-TRIFLUORO& is used as a building block in organic synthesis for its high reactivity and selectivity, which is crucial in the production of functional materials and pharmaceuticals.
Used in Organic Electronics:
In the field of organic electronics, 1-((TRIMETHYLSILYL)ETHYNYL)-4-TRIFLUORO& is utilized for its potential applications in developing new materials with unique electronic properties.
Used in Material Science:
1-((TRIMETHYLSILYL)ETHYNYL)-4-TRIFLUORO& is employed in material science for the development of new materials with distinctive characteristics, leveraging its reactivity and structural features to create innovative compounds with specific properties for various applications.

InChI:InChI=1/C12H13F3Si/c1-16(2,3)9-8-10-4-6-11(7-5-10)12(13,14)15/h4-7H,1-3H3

Upstream product

• 705-31-7 4-trifluoromethylphenylacetylene 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 40231-03-6 2-(trimethylsilylethynyl)thiophene 
• 1066-54-2 trimethylsilylacetylene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 75-77-4 chloro-trimethyl-silane 
• 75867-39-9 4-trimethylsilylethynyl aniline 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 119757-51-6 1,2-bis(4-(trifluoromethyl)phenyl)ethyne 
• 540-37-4 p-aminoiodobenzene 
• 455-13-0 4-Iodobenzotrifluoride 

Downstream Products

• 255733-11-0 (R)-(-)-1-(4-trifluoromethylphenyl)-1,2-ethanediol 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 370-99-0 4-trifluoromethyldiphenylethyne 
• 1192889-56-7 (Z)-1-(4-trifluoromethylphenyl)-2-(trimethylsilyl)ethene 
• 1184872-85-2 (Z)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-1,3-bis(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1184872-88-5 (Z)-1-(4-bromophenyl)-2-((4-bromophenyl)(hydroxy)methyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1184872-80-7 1-o-tolyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol 
• 1184872-87-4 (Z)-1-(4-(methoxycarbonyl)phenyl)-2-((4-(methoxycarbonyl)phenyl)(hydroxy)methyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1209467-42-4 (S,E)-trimethyl-[2-phenyl-1-(4-trifluoromethylbenzylidene)-but-3-enyl]silane 
• 1211510-03-0 (1,3-bis(2-pyridylimino)isoindoline(-1H))(4-(trifluoromethyl)phenylethynyl)platinum(II) 
• 1237683-33-8 1-benzyl-4-(4-(trifluoromethyl)phenyl)-1H-[1,2,3]-triazole 
• 1258456-57-3 C₁₄H₁₀F₆O₃ 
• 459832-23-6 2-(4-trifluoromethyl-phenyl-ethynyl)-pyridine 
• 1421932-27-5 ethyl 6-(hydroxymethyl)-4-((4-(trifluoromethyl)phenyl)ethynyl)pyridin-2-yl(phenyl)phosphinate 

Relevant academic research and scientific papers

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.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)

Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.

Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions

The molybdenum benzylidynes [ArCMo(OC(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)C6H4 (2b), p-(CF3)C6H4 (2c), p-(NO2)C6H4 (2d), or 4-(NO2)-3-(CF3)C6H3 (2e), and [p-(NO2)C6H4CMo(OC(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.

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.

Aggregation induced emission-emissive stannoles in the solid state

The optoelectronic and structural properties of six stannoles are reported. All revealed extremely weak emission in solution at 295 K, but intensive fluorescence in the solid state with quantum yields (ΦF) of up to 11.1% in the crystal, and of up to 24.4% (ΦF) in the thin film.

Designing Homogeneous Copper-Free Sonogashira Reaction through a Prism of Pd-Pd Transmetalation

Simultaneous introduction of two different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, leads to productive Pd-Pd transmetalation, subsequent reductive elimina

Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes

A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.

Post synthetic exchange enables orthogonal click chemistry in a metal organic framework

Biphenyl-4,4′-dicarboxylic acid derivatives containing either azide or acetylene functional groups were inserted into UiO-67 metal organic frameworks (MOFs) via post synthetic linker exchange. Sequential and orthogonal click reactions could be performed o