64583-21-7

Usage

Uses

Used in Organic Synthesis:
1-Fluoro-4-(2-(4-nitrophenyl)ethynyl)benzene is used as a building block for the preparation of various advanced materials. Its unique structure allows it to be a valuable component in the creation of complex organic molecules.
Used in Materials Science:
In the field of materials science, 1-Fluoro-4-(2-(4-nitrophenyl)ethynyl)benzene is utilized for its potential applications in developing new types of materials. Its properties make it suitable for use in the synthesis of liquid crystals and polymers, which have a wide range of applications in different industries.
Used in Research and Industrial Applications:
Due to its specific chemical and physical properties, 1-Fluoro-4-(2-(4-nitrophenyl)ethynyl)benzene serves as a valuable tool for research purposes. It aids chemists and material scientists in exploring new methods and applications, further expanding its utility in various industrial processes.
The potential uses of 1-Fluoro-4-(2-(4-nitrophenyl)ethynyl)benzene are continuously being investigated and expanded upon, as its unique characteristics present numerous opportunities for innovation and advancement in multiple disciplines.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 73584-06-2 diethyl α-chloro-4-fluorobenzylphosphonate 
• 54335-03-4 diphenyl phosphonate 
• 459-57-4 4-fluorobenzaldehyde 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 5281-22-1 1-(2,2-dichlorovinyl)-4-nitrobenzene 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 586-78-7 para-nitrophenyl bromide 
• 101456-16-0 diphenyl phosphonate 

Relevant academic research and scientific papers

Synthesis of Diarylacetylenes Bearing Electron-Withdrawing Groups via the Smiles Rearrangement

Nitrobenzyl benzothiazol-2-yl sulfones and nitrobenzyl 1-phenyl-1 H -tetrazol-5-yl sulfones react with chlorides of aromatic acids to form β-acyl derivatives. These products undergo the Smiles rearrangement resulting in the formation of the corresponding nitrophenyl arylacetylenes in 50-60% overall yields (approx. 75% per step). Sulfones bearing CF 3 or CN groups instead of a NO 2 substituent form mixtures of the acetylenes in moderate yields and benzyl aryl ketones in yields above 40%.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions

Two new pincer type Pd(II)-Schiff base complexes of the general formula [PdL1(PPh3)] 1 and [PdL2(PPh3)] 2, (where L1 = 2-(2,3-Dihydroxybenzylideneamino)phenolate and L2 = 2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamidate) were synthesised by the reaction of the palladium acetate with the corresponding ligand in methanol as yellow crystalline solids in high yields. Both complexes were fully characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, elemental analysis and single crystal X-ray diffraction studies. The crystal structures confirmed the tridentate nature of the pincer type Schiff base ligands and the distorted square planar geometry around the metal centre in both cases. The triphenylphosphine acted as an auxiliary ligand and occupied the fourth coordination site at palladium. The complexes were found to be efficient homogenous catalysts for a series of Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions at a low catalyst loading (0.08 mol%), and without the use of any additives. All organic products were fully characterized by 1H and 13C NMR studies.

Ligand- and copper-free Sonogashira and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles supported on in situ generated Al(OH)3

The ligand- and copper-free Sonogashira reaction of (Het)aryl halides (Br and Cl) with various terminal alkynes and the Heck coupling of (Het)aryl halides (Br and Cl) with a series of olefins, catalyzed by palladium nanoparticles supported on newly generated Al(OH)3, were developed. The catalyst can be readily recovered and reused 6 times without significant loss of activity and palladium leaching.

Recyclable palladium catalysts for the heck/sonogashira reaction under microwave-assisted thermomorphic conditions

The reaction of allyl palladium(II) chloride dimer and 4,4′-bis(RfCH2OCH2)-2,2′-bpy, 1a-b, in the presence of AgOTf resulted in the synthesis of cationic palladium complex, [Pd(η3-allyl)(4,4′-bis-(Rs

Thermoregulated copper-free Sonogashira coupling in water

The Sonogashira cross-coupling reaction between aryl halides and terminal alkynes was carried out smoothly in water over a thermoregulated ligand-palladium catalyst under copper-free conditions, resulting in good to excellent yields. The Sonogashira react

Bis(μ-iodo)bis((-)-sparteine)dicopper(I) catalyzed Sonogashira-type reaction under palladium and phosphine-free conditions

An efficient and inexpensive protocol for the Sonogashira-type cross coupling reactions of phenylacetylenes with a variety of haloarenes including activated aryl chlorides employing the structurally well-characterized bis(μ-iodo)bis((-)-sparteine)dicopper

CuI-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reactions using DABCO as ligand

In the presence of TBAB, CuI-catalyzed Suzuki-Miyaura cross-coupling of vinyl halides and aryl halides with arylboronic acids was conducted smoothly to afford the corresponding diarylethenes and polyaryls in moderate to good yields using DABCO (1,4-diazabicyclo[2.2.2]octane) as the ligand. We also found that the inexpensive CuI/DABCO catalytic system was effective for Sonogashira cross-couplings of aryl halides and vinyl halides. A variety of aryl halides and vinyl halides including activated aryl chlorides underwent the coupling with terminal alkynes in moderate to excellent yields.

Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions

PdCl2(PPh3)2 combined with TBAF under solvent-free conditions provided general and fast Sonogashira cross-coupling reactions of aryl halides with terminal alkynes. In particular, this protocol could be applied to the reactions of deactivated aryl chlorides. In the presence of 3 mol % of PdCl2(PPh3)2 and 3 equiv of TBAF, a number of ArX species (X = I, Br, Cl) were coupled with alkynes to afford the corresponding products in moderate to excellent yields under copper-, amine-, and solvent-free conditions.

Efficient and copper-free sonogashira cross-coupling reaction catalyzed by Pd(OAc)2/pyrimidines catalytic system

An efficient and copper-free catalyst system for Sonogashira cross-coupling reaction is presented. In the presence of 3 mol-% of Pd(OAc)2 and 6 mol-% of 2-aminopyrimidine-4,6-diol, various aryl iodides and bromides can be coupled smoothly with