766-47-2

Usage

Uses

Used in Chemical Synthesis:
2-Ethynyltoluene is used as a key intermediate in the synthesis of various organic compounds, including Ph2N(2-MeC6H4)C=CH2. Its unique structure with a triple bond and a methyl group on the toluene molecule makes it a versatile building block for creating a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Ethynyltoluene may be used as a starting material for the synthesis of various drug candidates. Its reactivity and ability to form different derivatives make it a valuable component in the development of new medications.
Used in Material Science:
2-Ethynyltoluene can be utilized in the development of advanced materials, such as polymers and composites, due to its ability to undergo dimerization and form various derivatives. These materials can be used in a range of applications, from coatings and adhesives to electronic devices and sensors.
Used in Research and Development:
As a compound with unique chemical properties, 2-Ethynyltoluene is also used in research and development for exploring new reactions, understanding its reactivity, and discovering potential applications in various fields.

InChI:InChI=1/C9H8/c1-3-9-7-5-4-6-8(9)2/h1,4-7H,2H3

Upstream product

• 3989-15-9 trimethyl[(2-methylphenyl)ethynyl]silane 
• 74346-22-8 1-(1-bromovinyl)-2-methylbenzene 
• 67-56-1 methanol 
• 593-53-3 Methyl fluoride 
• 536-74-3 phenylacetylene 
• 74-88-4 methyl iodide 
• 577-16-2 2-Methylacetophenone 
• 14677-15-7 3-(2-methylphenyl)-1-phenylprop-2-yn-1-one 
• 19164-64-8 1-methylenebenzocyclobutane 
• 460-12-8 Butadiyne 
• 108-88-3 toluene 
• 615-37-2 ortho-methylphenyl iodide 
• 1066-54-2 trimethylsilylacetylene 
• 471-25-0 Propiolic acid 

Downstream Products

• 93021-69-3 1-phenyl-3-(o-tolyl)prop-2-yn-1-ol 
• 59790-57-7 1-Trimethylsilanylethynyl-2-trimethylsilanylmethyl-benzene 
• 143392-24-9 4-(2-methylphenyl)-furan-2(5H)-one 
• 143392-20-5 3-(2-methylphenyl)-2,5-dihydrofuran-2-one 
• 259090-89-6 (Z)-2,2‘-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) 
• 328086-31-3 3-o-tolyl-1-{2-[(trimethylsilyl)ethynyl]phenyl}prop-2-yn-1-ol 
• 503309-91-9 bis-1,5-(2-methylphenyl)-1,4-pentadiyn-3-ol 
• 588699-90-5 ethyl 2-[(2-methylphenyl)ethynyl]-1-cyclopentenecarboxylate 
• 7517-82-0 methyl 3-(2-methylphenyl)-2-propynoate 
• 783370-40-1 3-{2-(2-methylphenyl)ethenyl}cyclohexanone 
• 783370-40-1 3-{2-(2-methylphenyl)ethenyl}cyclohexanone 

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.

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 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.

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.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Reaction discovery using acetylene gas as the chemical feedstock accelerated by the stop-flow micro-tubing reactor system

Acetylene gas has been applied as a feedstock under transition-metal catalysis and photo-redox conditions to produce important chemicals including terminal alkynes, fulvenes, and fluorinated styrene compounds. The reaction discovery process was accelerated through the use of stop-flow micro-tubing reactors. This reactor prototype was developed by joining elements from both continuous micro-flow and conventional batch reactors, which was convenient and effective for gas/liquid reaction screening. Notably, the developed transformations were either inefficient or unsuccessful in conventional batch reactors. Its success relies on the unique advantages provided by this stop-flow micro-tubing reactor system.

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 practical non-metal catalytic silicon of the amino protection of the new method (by machine translation)

The invention relates to a high efficiency, mild organic silicon reagent carbon silicon key fracture of the new method. The method of this reaction to the alkali is cheap and easy to obtain metal catalyst, in order to common commercial solvent as a reaction solvent and a hydrogen source, in the air and in the under mild conditions can be successfully catalytic trimethyl aryl silicon reagent or aryl alkyne base silicon reagent selectively generating carbon silicon key cracking hydrogenation reaction, the substrate universality is wide, functional group compatibility outstanding. The first innovative to realize the non-transition metal catalyzed carbon silicon key breaking reaction, also overcome the traditional method requires the use of greatly excessive inorganic alkali or an expensive metal catalyst to the limitation of the silicon of the amino protection, for the laboratory preparation and industry in the production of the organosilicon group deprotection provides a completely new strategy. (by machine translation)