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Usage

Uses

Used in Organic Synthesis:
Pentafluorophenetole is utilized as a solvent in organic synthesis, where its unique properties contribute to the efficiency and selectivity of chemical reactions.
Used in Organic Chemistry Research:
As a reagent, Pentafluorophenetole aids in the study and understanding of organic chemistry, particularly in reactions involving electron-withdrawing groups.
Used in Pharmaceutical Preparation:
Pentafluorophenetole is employed in the preparation of pharmaceuticals, leveraging its stability and reactivity to produce a range of medicinal compounds.
Used in Agrochemicals:
In the agrochemical industry, Pentafluorophenetole is used for the synthesis of various agrochemical products, contributing to the development of effective and stable pesticides and other agricultural chemicals.
Used in Electronic Materials:
Pentafluorophenetole also finds application in the preparation of electronic materials, where its properties can enhance the performance of certain electronic devices or components.
Used in Fluorous Chemistry:
Pentafluorophenetole has potential applications in the field of fluorous chemistry, where its fluorine content and stability are advantageous for specific chemical processes and separation techniques.
Used as a Precursor in Synthesis:
Furthermore, Pentafluorophenetole serves as a precursor in the synthesis of other fluorinated compounds, expanding its utility in the creation of diverse chemical products.

Upstream product

• 31665-24-4 1,3,4,5,5,6,6-heptafluoro-2-ethoxy-1,3-cyclohexadiene 
• 110-86-1 pyridine 
• 392-56-3 Hexafluorobenzene 
• 64-17-5 ethanol 
• 780-69-8 triethoxyphenylsilane 
• 377-70-8 perfluoro-1,3-cyclohexadiene 
• 141-52-6 sodium ethanolate 
• 816-65-9 N-(1-ethoxyvinyl)-N,N-dimethylamine 

Downstream Products

• 96028-38-5 3-ethoxy-7-phenyl-8-tert-butyl-1,2,4,5,6-pentafluorobicyclo<4.2.0>octatriene 
• 1617508-02-7 C₃₁H₂₀AuF₄NO 
• 96028-41-0 3-phenyl-4-methyl-7-ethoxy-1,2,5,6,8-pentafluoro<4.2.0>octatriene 

Relevant academic research and scientific papers

NHC Nickel Catalyzed Hiyama- and Negishi-Type Cross-Coupling of Aryl Fluorides and Investigations on the Stability of Nickel(II) Fluoroaryl Alkyl Complexes

The reactivity of [Ni(iPr2Im)4(μ-COD)] 1 (iPr2Im = 1,3-diisopropyl-imidazolin-2-ylidene, COD = 1,4-cyclooctadiene) in Hiyama- and Negishi-type cross-coupling reactions as well as the synthesis of several novel nickel fluoroaryl alkyl complexes is reported. Hiyama coupling of 1.1 equiv. perfluoroaromatics and 1 equiv. PhSi(OR)3 (R = Me, Et) with 5 mol-% of 1 as catalyst leads to the C–C coupling product ArF–Ph in good to fair yields. In presence of the additive NMe4F alkoxy transfer from PhSi(OR)3 to the perfluoroarene occurs to yield ArF–OR and PhSiF(OR)2. Negishi cross-coupling between C6F6 or C7F8 (1 equiv.), diorganozinc reagents [ZnR2] (R = Me, Et) (2.1 equiv.) and 5 mol-% 1 as the catalyst in toluene at 115 °C leads to ArF–R only in traces. However, NMR experiments revealed that nickel alkyl complexes are readily formed from the reaction of trans-[Ni(iPr2Im)2(F)(ArF)] with [ZnR2] (R = Me, Et). In course of these investigations, a series of novel nickel alkyl complexes trans-[Ni(iPr2Im)2(R)(ArF)] (R = Me, ArF = C6F5 2, C7F7 3, C12F9 4; R = Et, ArF = C6F5 5, C7F7 6, C12F9 7) have been synthesized in stoichiometric reactions starting from trans-[Ni(iPr2Im)2(F)(ArF)] (ArF = C6F5, C7F7, C12F9) and [ZnR2] (R = Me, Et) in thf at –78 °C. As these nickel alkyl complexes 2–7 are stable at room temperature in solution for several days with respect to reductive elimination, their thermal stability was investigated. Heating trans-[Ni(iPr2Im)2(Me)(C6F5)] 2 for 24 hours at 100 °C leads to 91 % unreacted complex 2 and only traces of reductive elimination product, i.e. C6F5Me, are formed. Furthermore, the nickel ethyl complex trans-[Ni(iPr2Im)2(Et)(C6F5)] 5 is also very stable, even with respect to β-hydride elimination. After heating this complex to 100 °C for 24 hours there is still 26 % unreacted 5 left.

REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. II. NUCLEOPHILIC SUBSTITUTION IN NITROHALOGENO AND POLYFLUORINATED AROMATIC COMPOUNDS

The possibility of aromatic nucleophilic substitution in liquid ammonia was investigated for the case of the reaction of p-nitrochlorobenzene, 2,4-dinitrochlorobenzene, hexafluorobenzene, bromopentafluorobenzene, pentafluorobenzene, and octafluoronaphthalene with a series of charged nucleophiles (potassium hydroxide and sulphite, alcoholates, sodium azide, thiophenolate, phenolate, and sulfide) at -70 to -33 deg C.It was shown that alkyl ethers of p-nitrophenol, phenyl p-nitrophenyl sulfide, 2,4-dinitrophenyl azide, polyfluorinaqted phenols, and their ethers can be obtained with good yields.Comparisons of the results with published data on the rate of the same reactions in other solvents shows that liquid ammonia is highly effective as a solvent for aromatic nucleophilic substitution reactions and in some cases makes it possible to avoid side processes.

Condensation of αβ-unsaturated amines with perfluoroarenes

Condensation of αβ-unsaturated amines (enamines, keten ON-acetals, ynamines) with perfluoroarenes (perfluorobenzene, perfluorotoluene, bromopentafluorobenzene, perfluoropyridine) leads to the formation of ketones, esters, and amines α-substituted by a perfluoroaryl group. In the case of enamines, C-arylation can be followed by intramolecular N-arylation, giving fluorinated tetrahydrocarbazoles which can then be dehydrogenated by chloranil to give fluorinated carbazoles.