766-98-3

Usage

Uses

Used in Liquid Crystals Industry:
4-Fluorophenylacetylene is used as an intermediate for the synthesis of liquid crystals. Liquid crystals are materials that exhibit properties between those of conventional liquids and solid crystals. They have a wide range of applications, including display technologies, such as liquid crystal displays (LCDs) found in televisions, computer monitors, and smartphones. The presence of the fluorine atom in 4-Fluorophenylacetylene contributes to the specific properties of the resulting liquid crystals, such as their stability, solubility, and electro-optical characteristics.
Used in Pharmaceutical Industry:
4-Fluorophenylacetylene serves as a pharmaceutical intermediate, which means it is a compound used in the synthesis of pharmaceutical drugs. The presence of the fluorine atom and the acetylene group in 4-Fluorophenylacetylene can impart specific biological activities to the final drug molecule, making it a valuable building block in the development of new medications. The use of 4-Fluorophenylacetylene in drug synthesis can lead to the creation of novel therapeutic agents with improved pharmacokinetic and pharmacodynamic properties.
Used in Organic Synthesis:
4-Fluorophenylacetylene is also used as an organic synthesis intermediate, which means it is a compound used in the preparation of other organic compounds. Its unique structure allows it to participate in various chemical reactions, such as cross-coupling reactions, cycloadditions, and electrophilic substitutions. This versatility makes it a valuable starting material for the synthesis of a wide range of organic compounds, including specialty chemicals, agrochemicals, and advanced materials.
Used in Vacuum Deposition Process:
4-Fluorophenylacetylene is utilized in the vacuum deposition process, which is a technique used to deposit thin films of materials onto a substrate. This process is widely used in various industries, such as electronics, optics, and materials science, to create coatings with specific properties, such as high electrical conductivity, optical transparency, or corrosion resistance. The use of 4-Fluorophenylacetylene in vacuum deposition can lead to the formation of thin films with unique properties, such as enhanced stability, improved adhesion, or tailored electronic characteristics.
Used in Sonogashira Type Cross Coupling Reaction:
4-Fluorophenylacetylene can be used in the Sonogashira type cross coupling reaction to synthesize aryl acetylenes. This reaction involves the coupling of an aryl or vinyl halide with an acetylene in the presence of a palladium catalyst and a copper co-catalyst. The use of 4-Fluorophenylacetylene in this reaction allows for the formation of substituted phenylacetylenes, such as 1-Ethynyl-4-fluorobenzene, which can be further used as intermediates in the synthesis of more complex organic compounds or materials with specific properties and applications.

InChI:InChI=1/C8H5F/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 87579-65-5 (C₆H₁₁)HgCCC₆H₄F 
• 3246-80-8 9-phenyl-9H-xanthene 
• 108-98-5 thiophenol 
• 130995-12-9 1-(4-fluorophenyl)-2-trimethylsilylacetylene 
• 66228-21-5 4-Fluor-α,α-dichlorethylbenzol 
• 405-99-2 para-fluorostyrene 
• 870122-74-0 2-bromo-1-(4-fluorophenyl)ethylene 
• 81233-93-4 2-methyl-4-(4-fluorophenyl)-3-butyn-2-ol 
• 352-34-1 4-fluoro-1-iodobenzene 
• 4301-14-8 acetylenemagnesium bromide 
• 115665-76-4 (Z)-1-(2-bromovinyl)-4-fluorobenzene 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1737-34-4 1-(chloroethynyl)-4-fluorobenzene 
• 5157-58-4 2,2-dichloro-1-(4-fluorophenyl)-ethan-1-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 87992-01-6 2-chloro-1-(4-fluorophenyl)butane-1,3-dione 
• 194936-20-4 2,3-Bis-[4-(4-fluoro-phenylethynyl)-phenyl]-quinoxaline 
• 194936-22-6 2,3-bis-[4-(4-fluoro-phenylethynyl)-phenyl]-quinoxaline-6-carboxylic acid 
• 229467-68-9 (E)-1-fluoro-4-[2-(phenylsulfanyl)vinyl]benzene 
• 782-17-2 2-(4-fluorophenyl)indole 
• 293757-12-7 2,7-bis[(4-fluorophenyl)ethynyl]-9H-fluoren-9-one 
• 308796-31-8 tert-butyl (4S)-4-[(1R)-3-(4-fluorophenyl)-1-hydroxy-2-propynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Relevant academic research and scientific papers

Piers′ Borane-Induced Tetramerization of Arylacetylenes

We herein report that the reaction of Piers′ borane, i. e. HB(C6F5)2, with an excess of arylacetylenes at room temperature leads to tetramerization of the acetylene and the diastereoselective formation of boryl-substituted

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.

Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source

Palladium-catalyzed one-pot four-component synthesis of β-cyano-α,β-unsaturated ketones by the reactions of aryl halides, calcium carbide, potassium hexacyanoferrate(II) and aroyl chlorides is described. The salient features of this protocol are the direct use of easy-to-handle acetylene source and eco-friendly cyanide source, wide scope of substrates with good functional group tolerance, and simple work-up procedure. (Figure presented.).

Trans Influence of Ligands on the Oxidation of Gold(I) Complexes

Gold(I) complexes are considered active species toward oxidative addition; current understanding indicates a different mechanism in contrast to other late transition metals, but a rational understanding of the reactivity profile is lacking. Herein, we propose that the accessibility of the gold(I) center to tri- or tetra-coordination is critical in the oxidative process involving a tri- or tetra-coordinate gold(I) with the oxidizing reagent as one of the ligands as an intermediate. A computational study of the geometry of (Phen)R3PAu(I)NTf2 complexes shows that the accessibility of such tricoordinate species shows a good correlation with the "trans influence" of phosphine ligands: the weak σ-donating phosphine ligands promote tricoordination of gold(I) complexes. The oxidative addition to the asymmetric tricoordinate (Phen)R3PAu(I)NTf2 complexes with alkynyl hypervalent iodine reagents was built. The kinetic profile of the oxidative addition exhibits a good relationship to the Hammett substituent parameter (ρ = 3.75, R2 = 0.934), in which the gold(I) complexes bearing less σ-donating phosphine ligands increase the rate of oxidative addition. The positive ρ indicates a high sensitivity of the oxidative addition to the trans influence. The reactivity profile of oxidative addition to a linear bis(pyridine)gold(I) complex further supports that the oxidative addition to gold(I) complexes is promoted by ligands with small trans influence.

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.

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.

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)

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.

Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes

N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoalkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.