579-39-5

Usage

Uses

Used in Organic Synthesis:
4,4'-Difluorobenzil is used as a key intermediate in the synthesis of various organic compounds, including 2,3-bis(4-fluorophenyl)thieno[3,4-b]pyrazine. Its unique chemical properties make it a valuable component in the creation of complex molecular structures.
Used in Polymer Synthesis:
In the polymer industry, 4,4'-difluorobenzil is used as a reactant in the preparation of poly(ether-α-diketone)s. It undergoes a nucleophilic substitution reaction with bisphenol A, contributing to the formation of these high-performance polymers.
Used in Pharmaceutical Chemistry:
4,4'-Difluorobenzil is utilized in the synthesis of DPPF (4,4′-difluoro-2,3-diphenylpyrazine) and MDPPF (4,4′-difluoro-5-methyl 2,3-diphenylpyrazine), which are compounds that can be used in the development of pharmaceuticals. These compounds are synthesized through direct condensation with ethylenediamine and 1,2-diaminopropane, respectively.
Used in Heterocyclic Chemistry:
4,4'-DIFLUOROBENZIL is also employed in the synthesis of 2,3-bis(4-fluorophenyl)quinoxaline, which is achieved through direct condensation with 1,2-phenylenediamine. The resulting heterocyclic compounds have potential applications in various fields, including materials science and pharmaceuticals.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 2959, 1994 DOI: 10.1016/S0040-4039(00)76671-8

Upstream product

• 565-04-8 α,α,α',α'-tetrachloro-4,4'-difluoro-bibenzyl 
• 2966-36-1 1-acetoxy-2,2,2-trichloro-1,1-bis-(4-fluoro-phenyl)-ethane 
• 459-57-4 4-fluorobenzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 53458-16-5 1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one 
• 24133-58-2 1,2-bis(4-fluorophenyl)-1,2-ethanediol 
• 2751-90-8 tetraphenylphosphonium bromide 
• 3457-46-3 4,4'-dichlorobenzil 
• 71-36-3 butan-1-ol 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 462-06-6 fluorobenzene 
• 100-52-7 benzaldehyde 
• 82128-66-3 2-(4-fluorophenyl)-2-(trimethylsilyloxy)acetonitrile 

Downstream Products

• 75075-55-7 5,6-Bis-(4-fluoro-phenyl)-[1,2,4]triazine-3-carboxylic acid methyl ester 
• 85301-96-8 4,5-Bis-(4-fluoro-phenyl)-2-(4-methoxy-benzylsulfanylmethyl)-1H-imidazole 
• 70028-85-2 5,5-di-(4-fluorophenyl)-hydantoin 
• 100072-90-0 C₁₈H₁₆F₂NO₄P 
• 721958-44-7 2-chloromethyl-5,5-bis(4-fluorophenyl)-3,5-dihydro-imidazol-4-one 
• 216225-13-7 bis-(4-morpholin-4-yl-phenyl)-ethanedione 
• 17078-27-2 4,4'-bis(dimethylamino)benzil 

Relevant academic research and scientific papers

Cooperative N-Heterocyclic Carbene/Nickel-Catalyzed Hydroacylation of 1,3-Dienes with Aldehydes in Water

The cooperative N-heterocyclic carbene/nickel-catalyzed redox-neutral hydroacylation of 1,3-dienes with aldehydes in water was reported. A wide range of aliphatic and aromatic aldehydes were directly coupled with 1,3-dienes, providing synthetically useful β,γ-unsaturated ketones or the corresponding ketones after hydrogenation in moderate to high yields and high atom economy. This protocol first demonstrated the compatibility of NHC catalysis with nickel catalysis. Water was used as the sole solvent, which is rarely reported in a cooperative metal/organic catalytic system.

P-fluorobenzil type oxime ester photoinitiator used for preparing photochromic material as well as preparation method and application thereof

The invention discloses a p-fluorobenzil type oxime ester photoinitiator for preparing a photochromic material as well as a preparation method and application thereof, and relates to the technical field of high-molecular materials. The photoinitiator disc

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Ruthenium/dendrimer complex immobilized on silica-functionalized magnetite nanoparticles catalyzed oxidation of stilbenes to benzil derivatives at room temperature

A new ruthenium/dendrimer complex stabilized on the surface of silica-functionalized nano-magnetite was fabricated and well characterized. The nano-catalyst showed good activity in the synthesis of benzil derivatives via the oxidation of stilbenes with high turnover frequency (TOF) at room temperature. Moreover, the catalyst could also be reused up to fifteen times without any loss of its activity.

Ring Closing Metathesis Approach for the Synthesis of o-Terphenyl Derivatives

A linear synthesis of o-terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl-1,2-diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization-driven dehydration then leads to a diverse set of electron rich and electron deficient o-terphenyls. Furthermore, oxidative coupling of electron rich o-terphenyls provides the corresponding triphenylene derivatives.

Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

ICl/AgNO3 Co-catalyzed radical oxidation of diaryl- A nd alkylarylalkynes into 1,2-diketones

A novel ICl/AgNO3 co-catalyzed radical oxidation of diaryl- A nd alkylarylalkynes into 1,2-diketones is reported. The reaction proceeded smoothly under mild conditions and generated 1,2-diketones in moderate to good yields with a good tolerance of functional groups. Furthermore, the obtained C4-(1,2-diketoaryl)isoxazoles could react smoothly with 1,2-diaminobenzene to form C4-(3-arylquinoxalin-2-yl)isoxazoles. At last, a new one-pot strategy for the synthesis of quinoxalines from 1,2-diphenylethynes and 1,2-diaminobenzene is also reported.

Magnetic magnetite nanoparticals catalyzed selective oxidation of Α-hydroxy ketones with air and one-pot synthesis of benzilic acid and phenytoin derivatives

A clean and efficient protocol for selective oxidation of α-hydroxy ketones using magnetic magnetite nanoparticals (Fe3O4·MNPs) as catalyst with air as green oxidant has been developed. Application of Fe3O4·MNPs was also proved to be successful in one-pot synthesis of benzilic acid and phenytoin derivatives. The facile one-pot procedure enhanced the production efficiency, shortened the reaction time and minimized the chemical waste. Notably, the catalyst can be reused at least for five times without any appreciable loss of its activity.

Umpolung Reactivity of Aldehydes toward Carbon Dioxide

Carbon dioxide is an intrinsically stable molecule. Therefore, its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions. Reported here is a direct carboxylation reaction of aromatic aldehydes with carbon dioxide to afford α-keto acids as added-value products. In situ generation of a reactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25–40 °C, 1 atm CO2). The resulting α-keto acids served as a platform for α-amino acid synthesis by reductive amination reactions, illustrating the chemical synthesis of essential bioactive molecules from carbon dioxide.