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Usage

Uses

Used in Electronic and Optoelectronic Components:
4H,4'H-OCTAFLUOROBIPHENYL is used as a component in the manufacturing of electronic and optoelectronic devices due to its specific properties that make it suitable for these applications. Its fluorine content and molecular structure provide enhanced stability and performance in these high-tech components.
Used in Ink Spreading Compounds for Coatings:
In the printing industry, 4H,4'H-OCTAFLUOROBIPHENYL is used as an additive in ink spreading compounds for coatings, particularly for ink jet transparencies. Its incorporation into these compounds improves the ink's spreading and adhesion properties, resulting in better print quality and more consistent color reproduction.
Used for Improved Toner Flow:
4H,4'H-OCTAFLUOROBIPHENYL is also utilized in the toner industry to enhance the flow properties of toner particles. By adding 4H,4'H-OCTAFLUOROBIPHENYL to the toner formulation, it can improve the toner's流动性 (flowability), ensuring a smoother and more consistent printing process. This is particularly important in high-speed printing applications where toner flow can significantly impact the overall performance and quality of the printed material.

Upstream product

• 92-52-4 biphenyl 
• 1073339-11-3 4,4,5,5-tetramethyl-2-(2,3,5,6-tetrafluorophenyl)-1,3,2-dioxaborolane 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 511295-01-5 2,3,5,6-tetrafluorophenyl(dihydroxy)borane 
• 5243-24-3 3-iodo-1,2,4,5-tetrafluorobenzene 
• 95-94-3 1,2,4,5-tetrachlorobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 434-90-2 decafluorobiphenyl 
• 392-57-4 1,4-diiodo-2,3,5,6-tetrafluorobenzene 
• 2200-68-2 perfluoro-(4,4'-byphenyldiyl)-dihydrazine 
• 10386-84-2 4,4'-dibromo-2,3,5,6,2',3',5',6'-octafluoro-1,1'-biphenyl 

Downstream Products

• 1927-89-5 4,4'-bis(pentafluorophenylmercapto)-octafluorobiphenyl 
• 142781-24-6 {Ni(PCH₃(C₆H₅)2)2}2(C₆F₄C₆F₄)(C₆F₄C₆F₄H)2 
• 142781-21-3 Ni(PCH₃(C₆H₅)2)2(C₆F₄C₆F₄H)Br 
• 142781-23-5 {Ni(PCH₃(C₆H₅)2)2}2(C₆F₄C₆F₄)Br₂ 
• 142781-22-4 Ni(PCH₃(C₆H₅)2)2(C₆F₄C₆F₄H)2 
• 90635-28-2 (Ph₃P)Au(octafluorobiphenyl) 

Relevant academic research and scientific papers

Hydrodefluorination of Fluoroarenes Using Hydrogen Transfer Catalysts with a Bifunctional Iridium/NH Moiety

The hydrodefluorination of fluoroarenes with transfer hydrogenation catalysts using 2-propanol or potassium formate is described. With the aid of metal/NH cooperation, the C-N chelating Ir complexes derived from benzylic amines can efficiently promote the reduction involving the C-F bond cleavage under ambient conditions even in the absence of hydrosilanes or H2 gas, leading to the partially fluorinated products in good yields and with high selectivity.

Diazaphospholene-Catalyzed Hydrodefluorination of Polyfluoroarenes with Phenylsilane via Concerted Nucleophilic Aromatic Substitution

The metal-free catalytic C-F bond activation of polyfluoroarenes was achieved with diazaphospholene as the catalyst and phenylsilane as the terminal reductant. Density functional theory calculations suggested a concerted nucleophilic aromatic substitution mechanism.

Catalytic Hydrodefluorination via Oxidative Addition, Ligand Metathesis, and Reductive Elimination at Bi(I)/Bi(III) Centers

Herein, we report a hydrodefluorination reaction of polyfluoroarenes catalyzed by bismuthinidenes, Phebox-Bi(I) and OMe-Phebox-Bi(I). Mechanistic studies on the elementary steps support a Bi(I)/Bi(III) redox cycle that comprises C(sp2)-F oxidative addition, F/H ligand metathesis, and C(sp2)-H reductive elimination. Isolation and characterization of a cationic Phebox-Bi(III)(4-tetrafluoropyridyl) triflate manifests the feasible oxidative addition of Phebox-Bi(I) into the C(sp2)-F bond. Spectroscopic evidence was provided for the formation of a transient Phebox-Bi(III)(4-tetrafluoropyridyl) hydride during catalysis, which decomposes at low temperature to afford the corresponding C(sp2)-H bond while regenerating the propagating Phebox-Bi(I). This protocol represents a distinct catalytic example where a main-group center performs three elementary organometallic steps in a low-valent redox manifold.

Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4

Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH4. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E/Z isomerization.

Palladium-Catalyzed Homocoupling of Highly Fluorinated Arylboronates: Studies of the Influence of Strongly vs Weakly Coordinating Solvents on the Reductive Elimination Process

C-C reductive elimination from [PdL2(C6F5)2] to form polyfluorinated biaryls has been a challenge for over 50 years. Thus, palladium-catalyzed homocoupling of arylboronates (ArF-Bpin) containing two ortho-fluorine substituents is very difficult, as the reaction typically stops at the [PdL2(ArF)2] stage after two transmetalation steps. The transmetalated complexes cis-[Pd(MeCN)2(C6F5)2] (3a), cis-[Pd(MeCN)2(2,4,6-C6F3H2)2] (3b), and cis-[Pd(MeCN)2(2,6-C6F2H3)2] (3e) have been isolated from the reaction of ArF-Bpin with Pd(OAc)2 in acetonitrile solvent, with no homocoupling observed. However, catalytic homocoupling proceeds smoothly in a "weakly coordinating" arene solvent as long as no ancillary ligands or coordinating solvents are present. DFT computations reveal that the active catalyst formed by arene solvent coordination leads to an overall reduced barrier for the reductive elimination step compared to the formation of stable [PdL2(ArF)2] complexes in the presence of a donor ligand or solvent L.

Hydrodefluorination of functionalized fluoroaromatics with triethylphosphine: A theoretical and experimental study

Recently we reported the metal free hydrodefluorination of selected fluoroaromatics using triethylphosphine as the sole defluorinating agent. That prompted us to evaluate the mechanistic proposal and in the light of these results, along with new experimental evidence, we have now modified the initial proposal. The new mechanism avoids the highly energetic β-elimination step of roughly 71 kcal mol-1 for hexafluorobenzene and pentafluoropyridine at 393.15 K, invoking the participation of water. The use of D2O confirmed the role of water as the hydrogen source, yielding the corresponding deutero-defluorinated products; DFT calculations agree with this new proposed mechanism. We also report herein the use of this one-pot hydrodefluorination method applied to a broader number of fluoroaromatic derivatives; some of them allowed the collection of key mechanistic evidence.

Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

A transition-metal-free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion-corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CSNAr) process.

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki-Miyaura Cross Coupling with Electron-Poor Substrates

Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still inaccessible to date. Here we report a general strategy for the synthesis of a wide range of highly fluorinated biphenyls. In our studies we investigated crucial parameters, such as different phosphine ligands and the influence of various nucleophiles and electrophiles with different degrees of fluorination. These results extend the scope of the already very versatile Suzuki-Miyaura reaction toward the synthesis of very electron-poor products, making these more readily accessible. The presented methodology is scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts.

Competition of Nucleophilic Aromatic Substitution, σ-Bond Metathesis, and syn Hydrometalation in Titanium(III)-Catalyzed Hydrodefluorination of Arenes

Several functionalized and non-functionalized perfluoroarenes were catalytically transformed into their para-hydrodefluorinated products by using catalytic amounts of titanocene difluoride and stoichiometric amounts diphenylsilane. Turnover numbers of up to 93 were observed. Solution density functional theory calculations at the M06-2X/TZ(PCM)//M06-2X/TZ(PCM) level of theory provided insight into the mechanism of TiIII-catalyzed aromatic hydrodefluorination. Two different substrate approaches, with a Ti–F interaction (pathway A) and without a Ti–F interaction (pathway B), are possible. Pathway A leads to a σ-bond metathesis transition state, whereas pathway B proceeds by means of a two-step mechanism through a syn-hydrometalation intermediate or through a Meisenheimer intermediate. Both pathways are competitive over a broad range of substrates.

Photocatalytic hydrodefluorination: Facile access to partially fluorinated aromatics

Polyfluorinated aromatics are essential to materials science as well as the pharmaceutical and agrochemical industries and yet are often difficult to access. This Communication describes a photocatalytic hydrodefluorination approach which begins with easily accessible perfluoroarenes and selectively reduces the C-F bonds. The method allows facile access to a number of partially fluorinated arenes and takes place with unprecedented catalytic activity using a safe and inexpensive amine as the reductant.