527-21-9

Usage

Uses

Used in Chemical Synthesis:
TETRAFLUORO-1,4-BENZOQUINONE is used as a synthetic agent for the preparation of symmetrical or unsymmetrical ethers. This is achieved through the oxidation-reduction condensation reaction involving the coupling of two alcohols, showcasing its utility in creating complex chemical structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TETRAFLUORO-1,4-BENZOQUINONE serves as a crucial intermediate in the synthesis of the azocino[4,3-b]indole scaffold. This scaffold is essential for the preparation of (±)-dasycarpidone, a compound with potential therapeutic applications.
Used in Chiral and Racemic Compounds:
TETRAFLUORO-1,4-BENZOQUINONE is also utilized in the formation of chiral and racemic charge-transfer (CT) complexes with binaphthol. These complexes are significant in the field of asymmetric catalysis and have potential applications in various chemical and pharmaceutical processes.

InChI:InChI=1/C6F4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

Upstream product

• 771-63-1 2,3,5,6-tetrafluoro-1,4-benzenediol 
• 118-75-2 chloranil 
• 670-54-2 ethenetetracarbonitrile 
• 42439-31-6 tetrafluoro-p-benzosemiquinone radical anion 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 363-72-4 Pentafluorobenzene 
• 17540-47-5 4-nitro-2,3,4,5,6-pentafluorocyclohexa-2,5-dien-1-one 
• 7789-21-1 fluorosulphonic acid 
• 2992-91-8 2,4,6-Cl₃-C₆F₂OH 
• 769-39-1 2,3,5,6-tetraflourophenol 
• 970-16-1 4-hydroxy-2,3,5,6-tetrafluoro-4'-dimethylaminoazobenzene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 392-56-3 Hexafluorobenzene 
• 389-40-2 Pentafluoroanisole 

Downstream Products

• 771-63-1 2,3,5,6-tetrafluoro-1,4-benzenediol 
• 104830-40-2 N,N'-Dicyano-2,3,5,6-tetrafluoro-1,4-benzoquinonediimine 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 126179-76-8 2,3,5,6-Tetrafluoro-cis-3',4'-diphenylspiro<2,5-cyclohexadiene-1,2'-oxetan>-4-one 
• 126179-76-8 2,3,5,6-Tetrafluoro-trans-3',4'-diphenylspiro<2,5-cyclohexadiene-1,2'-oxetan>-4-one 
• 53279-70-2 tetrakis(pentafluorophenoxy)-1,4-benzoquinone 
• 110638-44-3 complex of 2,7-bis(methylthio)-1,6-dithiapyrene and p-fluoranil 

Relevant academic research and scientific papers

Photoassisted catalytic cleavage of the C-F bond in pentafluorophenol with ZnO and the effect of operational parameters

The photocatalytic cleavage of the C?F bond in pentafluorophenol (PFP) with ZnO using 254 and 365 nm UV light has been investigated under different conditions. The defluoridation was monitored using an ionometer with a fluoride ion selective electrode. The photocleavage was more effective under 254 nm than under 365 nm UV light. With 254 nm UV light, TiO2-P25, TiO 2 (anatase), ZnO, and ZrO2 photocatalyzed the deflouridation of PFP, whereas CdS, CdO, and SnO2 did not. The defluoridation is enhanced by the addition of oxidants such as KIO4, KClO3, (NH4)2S2O8, and KBrO3. The periodate ion is found to be the most efficient oxidant. The defluoridation intermediates were found to be tetrafluorodihydroxybenzene, trifluorotrihydroxybenzene, and tetrafluoroquinone. CSIRO 2007.

Polyoxometalate-based supramolecular porous frameworks with dual-active centers towards highly efficient synthesis of functionalized: P -benzoquinones

Selective oxidation of substituted phenols is an ideal method for preparing functionalized p-benzoquinones (p-BQs), which serve as versatile raw materials for the synthesis of a variety of biologically active compounds. Herein, two new polyoxometalate-based supramolecular porous frameworks, K3(H2O)4[Cu(tza)2(H2O)]2[Cu(Htza)2(H2O)2][BW12O40]·6H2O (1) and H3K3(H2O)3[Cu(Htza)2(H2O)]3[SiW12O44]·14H2O (2) (Htza = tetrazol-1-ylacetic acid), were synthesized and structurally characterized by elemental analysis, infrared spectroscopy, thermal analysis, UV-vis diffuse reflectance spectroscopy, and single-crystal X-ray and powder diffraction. The single-crystal X-ray diffraction analysis indicates that both compounds possess unique petal-like twelve-nucleated Cu-organic units composed of triangular and hexagonal metal-organic loops. In 1, the Cu-organic units are isolated and [BW12O40]5- polyoxoanions are sandwiched between staggered adjacent triangular channels in the structure. However in 2, the Cu-organic units extend into a two-dimensional layered structure, and the [SiW12O44]12- polyoxoanions occupy the larger hexagonal channels in the stacked structure. Both compounds as heterogeneous catalysts can catalyze the selective oxidation of substituted phenols to high value-added p-BQs under mild conditions (60 °C) with TBHP as the oxidant, particularly in the oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-p-benzoquinone (TMBQ, key intermediate in vitamin E production). Within 8-10 min, the yield of TMBQ is close to 100%, and oxidant utilization efficiency is up to 94.2% for 1 and 90.9% for 2. The turnover frequencies of 1 and 2 are as high as 5000 and 4000 h-1, respectively. No obvious decrease in the yield of TMBQ was observed after five cycles, which indicates the excellent sustainability of both compounds. Our study of the catalytic mechanism suggests that there is a two-site synergetic effect: (i) the copper ion acts as the catalytic site of the homolytic radical pathway; and (ii) the polyoxoanion acts as the active center of the heterolytic oxygen atom transfer pathway. This journal is

Oxidative degradation of toxic organic pollutants by water soluble nonheme iron(iv)-oxo complexes of polydentate nitrogen donor ligands

The ability of four mononuclear nonheme iron(iv)-oxo complexes supported by polydentate nitrogen donor ligands to degrade organic pollutants has been investigated. The water soluble iron(ii) complexes upon treatment with ceric ammonium nitrate (CAN) in aqueous solution are converted into the corresponding iron(iv)-oxo complexes. The hydrogen atom transfer (HAT) ability of iron(iv)-oxo species has been exploited for the oxidation of halogenated phenols and other toxic pollutants with weak X-H (X = C, O, S,etc.) bonds. The iron-oxo oxidants can oxidize chloro- and fluorophenols with moderate to high yields under stoichiometric as well as catalytic conditions. Furthermore, these oxidants perform selective oxidative degradation of several persistent organic pollutants (POPs) such as bisphenol A, nonylphenol, 2,4-D (2,4-dichlorophenoxyacetic acid) and gammaxene. This work demonstrates the utility of water soluble iron(iv)-oxo complexes as potential catalysts for the oxidative degradation of a wide range of toxic pollutants, and these oxidants could be considered as an alternative to conventional oxidation methods.

2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and preparation method thereof

The invention discloses 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and a preparation method thereof. The preparation method comprises diazotization: carrying out diazotization of a compound A and a compound B to obtain a compound C, reduction: reducing the compound C into a compound D, oxidation: oxidizing the compound D into a compound E, and condensation: condensing the compound E and malononitrile to obtain a compound F, wherein the compound F is 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and the compounds A, B, C, D, E and F are shown in the description. The preparation method has good environmental friendliness and a high yield of 80% or more, is simple and easy and is suitable for industrial production.

Reactivity of a Ru(iii)-hydroxo complex in substrate oxidation in water

A mononuclear RuIII-OH complex oxidizes substrates such as hydroquinones in water through a pre-equilibrium process based on adduct formation by hydrogen bonding between the RuIII-OH complex and the substrates. The reaction mechanism switches from hydrogen atom transfer to electron transfer depending on the oxidation potential of substrates. This journal is

Catalytic defluorination of perfluorinated aromatics under oxidative conditions using N-bridged diiron phthalocyanine

Carbon-fluorine bonds are the strongest single bonds in organic chemistry, making activation and cleavage usually associated with organometallic and reductive approaches particularly difficult. We describe here an efficient defluorination of poly- and perfluorinated aromatics under oxidative conditions catalyzed by the μ-nitrido diiron phthalocyanine complex [(Pc)Fe III(μ-N)FeIV(Pc)] under mild conditions (hydrogen peroxide as the oxidant, near-ambient temperatures). The reaction proceeds via the formation of a high-valent diiron phthalocyanine radical cation complex with fluoride axial ligands, [(Pc)(F)FeIV(μ-N)FeIV(F) (Pc+?)], which was isolated and characterized by UV-vis, EPR, 19F NMR, Fe K-edge EXAFS, XANES, and Kβ X-ray emission spectroscopy, ESI-MS, and electrochemical techniques. A wide range of per- and polyfluorinated aromatics (21 examples), including C6F6, C6F5CF3, C6F5CN, and C6F5NO2, were defluorinated with high conversions and high turnover numbers. [(Pc)FeIII(μ-N)Fe IV(Pc)] immobilized on a carbon support showed increased catalytic activity in heterogeneous defluorination in water, providing up to 4825 C-F cleavages per catalyst molecule. The μ-nitrido diiron structure is essential for the oxidative defluorination. Intramolecular competitive reactions using C6F3Cl3 and C6F3H 3 probes indicated preferential transformation of C-F bonds with respect to C-Cl and C-H bonds. On the basis of the available data, mechanistic issues of this unusual reactivity are discussed and a tentative mechanism of defluorination under oxidative conditions is proposed.

Synthesis of fluorine-containing 1,4-dioxa-2-azaspiro-[4.5]deca-2,6,9- trienes by reaction of polyfluorinated cyclohexa-2,5-dienones with nitrile oxides

4-Pentafluorophenoxy-, 4-nitro-, and 4-chloropentafluorocyclohexa-2,5-dien- 1-ones and 3,4,5-tris-(pentafluorophenoxy)trifluorocyclohexa-2,5-dien-1-one react with some benzonitrile and acetonitrile oxides exclusively at the carbonyl group, leading to the formation of mixtures of diastereoisomeric fluorinated 1,4-dioxa-2-azaspiro[4.5]deca-2,6,9-trienes in good yield.

Aerobic oxidation of hydroquinone derivatives catalyzed by polymer-incarcerated platinum catalyst

(Chemical Equation Presented) It's a lock-in! A remarkably wide substrate scope of hydroquinones are oxidized to quinones in high yields in a platinum-catalyzed process with as low as 0.05 mol% catalyst. The aerobic oxidation is catalyzed by platinum nanoclusters trapped in a styrene-based polymer network (see scheme, PI Pt=polymer-incarcerated nanoclusters). The catalyst could be reused at least 13 times without any loss of catalytic activity.

o-fluoranil chemistry: Diels-Alder versus hetero-Diels-Alder cycloaddition

(Chemical Equation Presented) The title quinone undergoes [4 + 2] cycloadditions in two ways, Diels-Alder on the ring and hetero-Diels-Alder by attack at the oxygens. The latter mode of reaction is strongly favored thermodynamically, but there is a kinetic bias favoring the normal Diels-Alder addition that often prevails, especially with cycloaddends that are not electron-rich.

Chemical consequences of fluorine substitution. Part 4. Diels-Alder reactions of fluorinated p-benzoquinones with Dane's diene. Synthesis of fluorinated D-homosteroids

Four fluorinated p-benzoquinones (2) have been reacted with Dane's diene (1) in Diels-Alder reactions and the formed fluorinated D-homosteroids were characterized. The number of products, their stereochemistry and stability depends on the fluorine substitution pattern of the corresponding fluorinated p-benzoquinones. If the p-benzoquinone (2) contains an unfluorinated double bond, this bond reacts faster with diene 1 yielding endo-products selectively. In contrast, [4+2]cycloadditions with 2,6-difluoro (2c) and 2,3,5,6-tetrafluorobenzoquinone (2d) gave the products with exo-orientation of the carbonyl part preferably.