766-97-2

Usage

Uses

Used in Organic Synthesis:
4-Ethynyltoluene is used as a key intermediate in the synthesis of various organic compounds, particularly in the formation of bis(bicyclic) products through the cycloaddition of alkynes to the AlN2C2 moiety. This process allows for the creation of complex molecular structures with potential applications in various fields.
Used in Liquid Crystals Industry:
4-Ethynyltoluene serves as an intermediate in the production of liquid crystals, which are essential components in display technologies such as LCD screens. Its unique molecular structure contributes to the development of liquid crystal materials with specific properties, enhancing their performance in electronic devices.

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

Upstream product

• 42107-37-9 α-chloro-p-methylstyrene 
• 122-00-9 para-methylacetophenone 
• 33458-08-1 1-(1,2-dibromoethyl)-4-methylbenzene 
• 40886-61-1 (α-ethoxycarbonyl-α-4-methylbenzoylmethylene)triphenylphosphorane 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 67-56-1 methanol 
• 593-53-3 Methyl fluoride 
• 536-74-3 phenylacetylene 
• 65114-80-9 1-(4-Methylphenyl)-1,1-dichlorethan 
• 60512-56-3 1-(2,2-dibromovinyl)-4-methylbenzene 
• 91347-88-5 1-(4-methylphenyl)-1-cyclobutene 
• 624-31-7 4-tolyl iodide 
• 4301-14-8 acetylenemagnesium bromide 
• 73839-44-8 (Z)-1-[2-bromovinyl]-4-methylbenzene 

Downstream Products

• 861050-53-5 4-Hydroxy-1-phenyl-2-p-tolyl-naphthalin 
• 102006-96-2 5,5'-di-(4-methylphenyl)-3,3'-bisisoxazole 
• 33491-05-3 1-(2-bromoethynyl)-4-methylbenzene 
• 33675-56-8 1-(iodoethynyl)-4-methylbenzene 
• 22666-07-5 di-p-tolylbutadiyne 
• 97023-74-0 1-(4-methylphenyl)-hexane-1,5-dione 
• 80221-02-9 4-(p-tolyl)but-3-yn-2-one 
• 93021-70-6 1-phenyl-3-(p-tolyl)prop-2-yn-1-ol 
• 79756-90-4 4-(4-methylphenyl)but-3-yn-2-ol 
• 57355-73-4 5-(p-tolyl)pent-4-yn-2-ol 
• 6089-01-6 1-<4-Methyl-phenyl>-5-phenyl-pentadiin-1,4 
• 93654-93-4 Phenylaethinyl-p-tolylaethinyl-carbinol 
• 16017-24-6 3-p-tolylprop-2-yn-1-ol 
• 42866-56-8 3,3-Diphenyl-2-p-tolyl-propenal 

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.

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.

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.

BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording Tetrahydroquinolines

An efficient BF3·OEt2-mediated propargyl alcohol rearrangement/[1,5]-hydride transfer/cyclization cascade for the synthesis of tetrahydroquinoline derivatives has been described. The substituents adjacent to triple bonds play an important role in the formation of ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products of formal trans-carbofluorination of internal alkynes. This method provides a rapid access to diverse heterocycles in moderate to excellent yields.

Palladium-Catalyzed Cascade Intramolecular Cyclization and Allylation of Enynoates with Allylic Alcohols

A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/allylation reaction of enynoates with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert C-C double bond of allylic alcohol through cross-coupling reaction and lead to the formation of allyl pyrone via β-OH elimination. This cascade cross-coupling reaction represents a direct and atom economic methodology for the construction of novel allyl pyrones in moderate to good yields.

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.

DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes

Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).

Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with: N -hydroxyanilines to form highly functionalized pyrrole derivatives

This work describes new N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to yield highly functionalized pyrrole derivatives. In a postulated mechanism, N-hydroxyaniline attacks the more electron-rich alkynes via regioselective N-attack to form unstable ketone-derived nitrones that react with their tethered alkynes via an intramolecular oxygen-transfer to form α-oxo gold carbenes. This new method is applicable to a short synthesis of a bioactive molecule, a PDE4 inhibitor.

An Additive-Free, Base-Catalyzed Protodesilylation of Organosilanes

We report an additive-free, base-catalyzed C-, N-, O-, and S-Si bond cleavage of various organosilanes in mild conditions. The novel catalyst system exhibits high efficiency and good functional group compatibility, providing the corresponding products in good to excellent yields with low catalyst loadings. Overall, this transition-metal-free process may offer a convenient and general alternative to current employing excess bases, strong acids, or metal-catalyzed systems for the protodesilylation of organosilanes.