457-68-1

Usage

Uses

Used in Organic Synthesis:
4,4'-Difluorodiphenylmethane is used as a key intermediate for the synthesis of various organic compounds. Its presence in the molecular structure allows for the creation of a wide array of fluorinated organic molecules, which are known for their unique chemical and physical properties. The fluorine atoms in 4,4'-Difluorodiphenylmethane can be replaced or modified, enabling the development of new compounds with tailored characteristics for specific applications.
Used in Pharmaceuticals:
In the pharmaceutical industry, 4,4'-Difluorodiphenylmethane is utilized as a building block for the development of new drugs. Its unique structure and properties can contribute to the design of innovative pharmaceutical agents with improved efficacy, selectivity, and safety profiles. The incorporation of fluorine atoms into drug molecules is known to enhance their metabolic stability, lipophilicity, and binding affinity to target proteins, which can lead to better therapeutic outcomes.
Used in Agrochemicals:
4,4'-Difluorodiphenylmethane is employed as a vital component in the production of agrochemicals, such as pesticides and herbicides. The introduction of fluorine atoms into these compounds can improve their performance by increasing their volatility, solubility, and persistence in the environment. This can result in more effective control of pests and weeds, leading to higher crop yields and better agricultural productivity.
Used in Dyestuff:
In the dyestuff industry, 4,4'-Difluorodiphenylmethane is used as a precursor for the synthesis of various dyes and pigments. The presence of fluorine atoms in the molecular structure can impart unique color properties and improve the stability of the dyes under different environmental conditions. This can lead to the development of new dyes with enhanced performance characteristics, such as increased resistance to fading, better colorfastness, and improved solubility in various media.

Upstream product

• 462-06-6 fluorobenzene 
• 365-24-2 4,4'-difluorobenzhydryl alcohol 
• 101-77-9 4,4'-diamino diphenyl methane 
• 107-15-3 ethylenediamine 
• 208588-17-4 2,2-Bis-(4-fluoro-phenyl)-indan-1,3-dione 
• 75-09-2 dichloromethane 
• 352-34-1 4-fluoro-1-iodobenzene 
• 312-33-4 dichloro-bis-(4-fluoro-phenyl)-methane 
• 108-90-7 chlorobenzene 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 101-76-8 4,4'-dichlorodiphenylmethane 
• 1765-93-1 4-fluoroboronic acid 
• 84640-22-2 4-fluorobenzyl N,N-dimethylcarbamate 
• 3859-77-6 toluene-4-sulfonic acid-(4-fluoro-benzyl ester) 

Downstream Products

• 502-00-1 p-fluorobenzyl acetate 
• 104869-82-1 4-fluorobenzyl nitrate 
• 350-46-9 4-Fluoronitrobenzene 
• 19422-37-8 1,1,2,2-tetrakis(4-fluorophenyl)ethane 
• 39769-55-6 4,4′-difluorodiphenylmethyl cation 
• 1198215-02-9 3,3-bis(4-fluorophenyl)-1-phenylpropan-1-one 
• 1048954-70-6 (4-bis(4-fluorophenyl)methylphenyl)phenylmethane 
• 1048954-73-9 C₃₉H₂₇F₄⁽¹⁺⁾ 
• 1310713-66-6 C₃₉H₂₈F₄ 
• 1048954-71-7 bis(4-bis(4-fluorophenyl)methylphenyl)methyl-trimethylsilane 

Relevant academic research and scientific papers

Novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof

The invention relates to a novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof, especially the phenyl fluoride and derivatives thereof. The invention especially relates to a novel environment-friendly process for synthesizing phenyl fluoride and diphenyl ketone fluoride, which are the raw materials for preparing polyaryl-ether-ketone PAEK. The invention discloses the method that is more effective and environment-friendly for preparing the compounds through a Friedel-Crafts reaction, and further a more environment-friendly process, and provdies beneficial catalysts. Another object of the present invention is to employ the Friedel-Crafts reaction and adopts the beneficial catalysts, wherein the catalyst can be easily combined with the fluoridation reaction which can be carried out before, or after the Friedel-Crafts reaction. Herein, another object of the invention is to use the catalyst in the Friedel-Crafts reaction, wherein the catalyst can work in both the Friedel-Crafts reaction and the fluoridation reaction.

Dual Nickel- And Photoredox-Catalyzed Reductive Cross-Coupling of Aryl Halides with Dichloromethane via a Radical Process

The first catalytic strategy to harness a new chloromethane radical from dichloromethane under dual Ni/photoredox catalytic conditions has been developed. Compared with traditional two-electron reductive process associated with metallic reductants, this method via a single-electron approach can proceed under exceptionally mild conditions (visible light, ambient temperature, no strong base) and exhibits complementary reactivity patterns. It affords a broad scope of many functional groups, including alkenyl, which suffers cyclopropanation in previous routes. The diarylmethane-d2 compounds can be readily available with this transformation.

+: A Masked Potent Boron Lewis Acid

The chemistry of the boron cation has been revitalized in the past decade due to its newfound application in stoichiometric and catalytic organic reactions. To extend the frontier of boron cation catalysis, we came to discover that a mesityl-substituted η5-Cp*-coordinated boron cation could serve as a powerful Lewis acid for organic catalytic transformations. The boron cation [Cp*B-Mes][B(C6F5)4] ([1][B(C6F5)4]) stabilized in a boronium-like electronic structure binds to Et3PO readily and displays an acceptor number exceeding that of B(C6F5)3 on the Gutmann-Beckett acidity scale. The steric and electronic stabilization exerted by the electron-donating Cp? renders the highly Lewis acidic boron cation an easy-to-handle catalyst for hydrodeoxygenation of aryl ketones at ambient temperature. The exceptional catalytic performance of [1]+ implies that the incorporation of a coordinatively flexible substituent at boron is critical in bringing catalytic activity and stability to boron cation catalysts.

Super electron donor-mediated reductive desulfurization reactions

The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

Reversible Generation of Labile Secondary Carbocations from Alcohols in the Nanospace of H-Mordenite and Their Long-Lasting Preservation at Ambient Temperature

Secondary carbocations are rarely observed spectrometrically for prolonged durations at ambient temperatures because of their instability. In this study, when 4,4′-difluorobenzhydrol (1) was mixed with H-mordenite (H-Mor), the 4,4′-difluorodiphenylmethyl cation (2) was generated as the main product, identified by UV-vis and 13C-MAS NMR spectroscopies, and was preserved for over 1 week at ambient temperature. Surprisingly, the polymerization and disproportionation of 1 barely proceeded within the micropores of H-Mor. However, these side reactions prevailed in TfOH and formation of 2 was not observed. Preservation of other secondary carbocations from benzhydrol, 4,4′-dichlorobenzhydrol, and 9-fluorenol was also realized in H-Mor. It was confirmed that the generation of 2 from 1 was controlled by thermodynamic equilibrium rather than kinetic regulations. The equilibrium between 2 and 1 was accompanied by reversible chromism, which could be easily controlled by altering the moisture content in H-Mor. Moreover, novel insights into specific acid catalysis in zeolites densely populated with acid sites on the inner surface of micropores are described herein.

Preparation method of 4,4'-difluorobenzophenone

The invention discloses a preparation method of 4,4'-difluorobenzophenone, wherein the method includes the following preparation steps: (1) preparing a fluoroboric diazonium salt; (2), adding the fluoroboric diazonium salt obtained in the step (1), a catalyst and a solvent into a beaker provided with a distillation device and a BF3 gas absorption device, and carrying out reduced pressure distillation, to obtain 4,4'-difluorodiphenylmethane; (3), loading 4,4'-difluorodiphenylmethane into a flask, adding 24% dilute nitric acid and a catalyst, heating to a reflux temperature, dropping a 55% nitric acid, completing dropping within about 4 h, after the dropping is completed, continuing to carry out a reaction for 2 h, cooling to room temperature, separating crystals out, filtering, reused the filtrate, recrystallizing the filter material with 70% ethanol, and drying to obtain white flaky 4,4'-difluorobenzophenone crystals. The process and operation practicability is high, the steps are simple, requirements on equipment are low, the method is suitable for industrialized production, the product yield reaches 95% or more and the content reaches 99.8% or more.

Ethers as hydrogen sources in BF3·OEt2 promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons

A novel ether/BF3 reductive system has been described, in which diphenylmethanols and their ether and ester derivatives are used as starting materials. Reductions are performed in ether under reflux and an argon atmosphere, and the addition of extra water is beneficial to this reduction. A series of alkanes are able to be prepared with good to excellent yields. A deuterated experiment exhibits that the reductive hydrogen is generated from ether. The mechanism is discussed in detail to explain the observed reactivity.

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids

The Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids was achieved in an environmentally benign medium. Using water as the sole solvent, such transformation took place very well to give the desired diarylmethane derivatives in good to almost quantitative yields in the presence of a well-defined NHC-Pd(ii)-Im complex under mild conditions. It is worth noting here that this is the first example of benzyl carbamates used in coupling reaction, thus affording a new method for the formation of diarylmethanes by palladium-catalyzed C-O bond activation.

N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl sulfonates with arylboronic acids

The first example of palladium-catalyzed Suzuki-Miyaura coupling between benzyl sulfonates and arylboronic acids was reported in this paper. In the presence of a well-defined, air-stable and easily available NHC-Pd(ii)-Im complex, all reactions worked well to give the desired products in good to almost quantitative yields under the optimal conditions. Electron-rich, -neutral, -poor and sterically-hindered substituents on both substrates are tolerated in such transformation, providing a convenient, efficient and alternative method for the synthesis of diarylmethanes.