40230-90-8

Usage

Uses

Used in Organic Synthesis:
3-[(Trimethylsilyl)ethynyl]toluene is used as a building block in organic synthesis for its ability to form more complex molecules, contributing to the development of advanced chemical structures.
Used in Material Production:
In the Material Production Industry, 3-[(Trimethylsilyl)ethynyl]toluene is used as a precursor for the development of various materials, including liquid crystals, polymers, and pharmaceuticals, due to its reactivity and capacity to be incorporated into these substances.
Used in Pharmaceutical Development:
3-[(Trimethylsilyl)ethynyl]toluene is utilized as a precursor in the pharmaceutical industry for the synthesis of new drugs, leveraging its reactivity to create molecules with potential therapeutic applications.

Upstream product

• 625-95-6 3-Iodotoluene 
• 1066-54-2 trimethylsilylacetylene 
• 591-17-3 meta-bromotoluene 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 75-77-4 chloro-trimethyl-silane 
• 766-82-5 1-ethynyl-3-methyl-benzene 

Downstream Products

• 766-82-5 1-ethynyl-3-methyl-benzene 
• 328086-32-4 3-m-tolyl-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-ol 
• 328086-37-9 3-m-tolyl-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-one 
• 1044501-72-5 1-benzyl-4-(3-methylphenyl)-1H-1,2,3-triazole 
• 1209467-40-2 (S,E)-trimethyl-[1-(3-methylbenzylidene)-2-phenylbut-3-enyl]silane 
• 14674-99-8 1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one 
• 1435769-89-3 4-(m-tolylethynyl)pyridine 
• 1435770-02-7 C₂₁H₁₅F₂N₃ 
• 1435770-07-2 C₂₁H₁₆FN₃ 
• 1435770-12-9 C₂₁H₁₇N₃O 
• 1435770-17-4 C₂₅H₁₈FN₃ 
• 1435770-22-1 4-(2-(4-(methylthio)phenyl)-4-(m-tolyl)-1H-imidazol-5-yl)pyridine 
• 1435770-27-6 C₂₂H₁₉N₃OS 
• 585-74-0 3-Methylacetophenone 

Relevant academic research and scientific papers

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.

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.

Asymmetric Hydrosilylation of β-Silyl Styrenes Catalyzed by a Chiral Palladium Complex

A palladium complex coordinated with a chiral SIPHOS ligand was evaluated as an efficient catalyst for asymmetric hydrosilylation of β-silyl styrenes with trichlorosilane and 23 1,2-bis(silyl) chiral compounds were produced. Good to excellent enantioselec

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation

A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

Blue-shifted aggregation-induced emission of siloles by simple structural modification and their application as nitro explosive chemosensors

To induce blue-shifted emission of siloles, two tolyl-substituted derivatives-1,1-diphenyl-2,3,4,5-tetra(m-tolyl)-1H-silole (m-TS) and 1,1-diphenyl-2,3,4,5-tetra(o-tolyl)-1H-silole (o-TS)-were prepared, and their photophysical properties were compared with those of a reference compound, hexaphenylsilole (HPS). By substituting methyl groups at ortho positions of peripheral tetraphenyl rings on the silacyclopentadiene ring, intramolecular rotations could be successfully controlled and the photophysical properties were varied, while substituting methyl groups at meta positions showed similar photophysical properties compared with the case of HPS. That is, simple structural modification at the ortho position significantly affects the geometry and the photophysical properties of silole, which leads to blue-shifted emission. Finally, two tolyl-substituted siloles and HPS were employed as chemosensors for the detection of nitro explosives, and o-TS showed the highest sensing ability.

A phosphine-free, atom-efficient cross-coupling of aryl iodides with triarylindiums or trialkynylindiums catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous atom-efficient cross-coupling reaction of aryl iodides with triarylindiums or trialkynylindiums was achieved in THF at 68 °C by using 1 mol% of MCM-41-immobilized palladium(0)-Schiff base complex [MCM-41-N,N-Pd(0)] as catalyst, yielding a variety of unsymmetrical biaryls and arylalkynes in good to excellent yields. The heterogeneous palladium(0) catalyst could easily be prepared via a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution and recycled at least 10 times without significant loss of activity.

Microwave-assisted copper- and palladium-catalyzed sonogashira-type coupling of aryl bromides and iodides with trimethylsilylacetylene

An efficient and rapid method was developed for the synthesis of 1-aryl-2-(trimethylsilyl)acetylene. Copper and palladium-catalyzed sonogashira-type coupling of trimethylsilylacetylene and aryl bromides or iodides in the presence of triethylamine as base

Cleavage of the Carbon–Carbon Triple Bonds of Arylacetylenes for the Synthesis of Arylnitriles without a Metal Catalyst

Cleavage of the carbon–carbon triple bonds of alkynes was achieved, which led to the synthesis of arylnitriles under transition-metal-free conditions. A vast range of terminal alkyne substrates underwent this reaction to provide the corresponding nitriles in moderate to good yields with good functional group tolerance.

Formal [4+ 2] reaction between 1,3-diynes and pyrroles: Gold(I)-catalyzed indole synthesis by double hydroarylation

Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.

Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization

(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.