3989-15-9

Usage

Uses

Used in Organic Synthesis:
2-Trimethylsilylethynyltoluene is utilized as a building block in organic synthesis for its ability to undergo Sonogashira cross-coupling reactions. This application is crucial for creating new carbon-carbon bonds, which are fundamental in the construction of complex organic molecules and pharmaceuticals.
Used in Semiconductor Applications:
In the field of materials science, 2-trimethylsilylethynyltoluene is explored for its potential use in semiconductor applications. Its electron-donating properties, along with the ability to form stable films on various substrates, make it a promising candidate for improving the performance of semiconductor devices and potentially contributing to the development of new electronic materials.
Used in Materials Science:
2-Trimethylsilylethynyltoluene's capacity to form stable films on substrates positions it as a valuable component in materials science. It can be used to develop new materials with specific properties, such as enhanced conductivity or stability, which are essential in various industrial applications, including electronics and coatings.

InChI:InChI=1/C12H16Si/c1-11-7-5-6-8-12(11)9-10-13(2,3)4/h5-8H,1-4H3

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 1066-54-2 trimethylsilylacetylene 
• 615-37-2 ortho-methylphenyl iodide 
• 75-77-4 chloro-trimethyl-silane 
• 766-47-2 1-ethynyl-2-methylbenzene 

Downstream Products

• 766-47-2 1-ethynyl-2-methylbenzene 
• 24644-78-8 4-methylindanone 
• 110598-37-3 4-((Z)-1-o-Tolyl-2-trimethylsilanyl-vinyl)-phenol 
• 442904-02-1 {[2-(bromomethyl)phenyl]ethynyl}trimethylsilane 
• 7517-82-0 methyl 3-(2-methylphenyl)-2-propynoate 
• 866240-60-0 (Z)-1-(2-tolyl)-4-trimethylsilyl-1-buten-3-yne 
• 259090-89-6 (Z)-2,2‘-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) 
• 521305-63-5 3-(ortho-tolyl)propiolaldehyde 
• 503309-97-5 2-(1,1-dimethylethyl)-6-(2-methylphenyl)thiapyran-4-one 
• 503309-89-5 1-(1,1-dimethylethyl)-5-(2-methylphenyl)-1,4-pentadiyn-3-ol 

Relevant academic research and scientific papers

Naturally occurring 5-[2-thienyl)ethynyl]thiophene-2-carbaldehyde through a short synthesis of diarylacetylenes

Title compound and related diarylacetylenes were synthesized via a one-pot procedure starting from aryliodide and trimethylsilylacetylene.

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.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes

Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.

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

Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with: N -substituted pyrroles

Metal-free hydroarylation of alkynes with N-substituted pyrroles is shown to be most efficiently mediated by B(C6F5)3 to yield 12 variants of dipyrrole-alkanes, a mono-hydroarylation product and a tetrahydroarylation produ

Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes

Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.

Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes

The [2+2] cycloaddition is a versatile strategy for the synthesis of strained cyclobutenes of high synthetic value. In this study, two efficient intermolecular [2+2] cycloadditions between two different types of chloroalkynes and unactivated alkene are realized with gold catalysis. Of significance is that the reaction works with challenging monosubstituted unactivated alkenes, which is unprecedented in gold catalysis and scarcely documented in other metal-catalyzed/promoted reactions; moreover, the reaction exhibits excellent regioselectivities, which are much better than those reported in literature. With 1,2-disubstituted unactivated alkenes, the reaction is largely stereospecific. The cyclobutene products can be prepared in nearly gram scale and readily undergo further reactions including various cross-coupling reactions using the C(sp2)-Cl and/or C(sp2)-SPh bond, which in turn substantially broaden the scope of accessible cyclobutenes and enhance the synthetic utility of this bimolecular reaction.