2787-79-3

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5,6-Tetrafluoro-4-(trifluoromethyl)phenol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique fluorinated structure contributes to the development of new drugs with improved properties, such as enhanced solubility, stability, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenol is utilized as a key building block for the production of novel agrochemicals. Its incorporation into these compounds can lead to the development of more effective and environmentally friendly pesticides and herbicides.
Used in Material Science:
2,3,5,6-Tetrafluoro-4-(trifluoromethyl)phenol is employed in the field of material science for the development of advanced materials with unique properties. Its fluorinated structure can enhance the performance of polymers, coatings, and other materials, making them more resistant to wear, corrosion, and environmental degradation.
Used in Chemical Research:
As an aryl fluorinated building block, 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenol is a valuable compound in chemical research. It is used in the synthesis of various organic and organometallic compounds, contributing to the advancement of chemical knowledge and the discovery of new chemical reactions and processes.

InChI:InChI=1/C7HF7O/c8-2-1(7(12,13)14)3(9)5(11)6(15)4(2)10/h15H

Upstream product

• 349094-68-4 4-Trifluoromethyl-2,3,5,6-tetrafluorophenyl prop-2-enyl ether 
• 434-64-0 perfluorotoluene 
• 13471-86-8 1-tert-Butoxy-2,3,5,6-tetrafluoro-4-trifluoromethyl-benzene 

Downstream Products

• 384-65-6 1-chloro-2,2,2-trifluoroethylbenzene 
• 104676-21-3 α-trifluoromethylbenzyl 4-trifluoromethyltetrafluorophenyl ether 
• 52144-71-5 4-Isopropyl-2,3,5,6-tetrafluorphenol 
• 769-39-1 2,3,5,6-tetraflourophenol 

Relevant academic research and scientific papers

Mechanism of Oxidative Activation of Fluorinated Aromatic Compounds by N-Bridged Diiron-Phthalocyanine: What Determines the Reactivity?

The biodegradation of compounds with C?F bonds is challenging due to the fact that these bonds are stronger than the C?H bond in methane. In this work, results on the unprecedented reactivity of a biomimetic model complex that contains an N-bridged diiron-phthalocyanine are presented; this model complex is shown to react with perfluorinated arenes under addition of H2O2 effectively. To get mechanistic insight into this unusual reactivity, detailed density functional theory calculations on the mechanism of C6F6 activation by an iron(IV)-oxo active species of the N-bridged diiron phthalocyanine system were performed. Our studies show that the reaction proceeds through a rate-determining electrophilic C?O addition reaction followed by a 1,2-fluoride shift to give the ketone product, which can further rearrange to the phenol. A thermochemical analysis shows that the weakest C?F bond is the aliphatic C?F bond in the ketone intermediate. The oxidative defluorination of perfluoroaromatics is demonstrated to proceed through a completely different mechanism compared to that of aromatic C?H hydroxylation by iron(IV)-oxo intermediates such as cytochrome P450 Compound I.

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.

Pyrolysis reactions of 4-phenyl-2,3,5,6-tetrafluorophenyl prop-2-enyl ether and 4-trifluoromethyl-2,3,5,6-tetrafluorophenyl prop-2-enyl ether: Remarkable rearrangement reactions of intramolecular Diels-Alder products.: Mechanistic implications of a new thermal retro-Diels-Alder reaction to cyclohexa-2,4-dienylmethyl fluoroketenes and recyclisations

The pyrolyses of 4-phenyl-2,3,5,6-tetrafluorophenyl prop-2-enyl ether (26) under flash vapour phase (FVP) conditions at 350°C and of 4-trifluoromethyl-2,3,5,6-tetrafluorophenyl prop-2-enyl ether (27) on heating in vacuo at 169°C give mixtures of products which include 3-phenyl-2,4,5,7-tetrafluorotricyclo[3.3.1.02,7]non-3-ene-6-one (28), and 3-trifluoromethyl-2,4,5,7-tetrafluorotricyclo[3.3.1.0 2,7]non-3-ene-6-one (31), respectively, the products of one of the two possible intramolecular Diels-Alder reactions of the Claisen rearrangement intermediates 2. FVP of 26 at 430°C and 27 at 450°C give the bicyclic compounds 7-phenyl-2,5β,6,7aβ-tetrafluoro-3aβ,4,5,7a-tetrahydroinden-1-one (34) and 7-trifluoromethyl-2,5β,6,7aβ-tetrafluoro-3aβ,4,5,7a- tetrahydroinden-1-one (37), respectively. It is proposed that these latter two compounds are formed via two possible intermediates produced by recyclisations of the tethered 2,4,5-trifluoro-3-(substituent)-2,4-cyclohexadienylmethyl fluoroketene (23), itself formed via new retro-cyclisation reactions of 28 and 31, respectively. Also formed from 27 via 31 is 1,2,4β,5,7-tetrafluoro-3-(trifluoromethyl)bicyclo[3.3.1]nona-2,6-dien-8-one (39).