20867-94-1

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5,6-Tetrafluoro-4-(trifluoromethyl)benzyl alcohol is used as a building block for the synthesis of various pharmaceuticals. Its unique structure and properties contribute to the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, 2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzyl alcohol serves as a key intermediate in the production of agrochemicals. Its incorporation into these compounds can enhance their performance and selectivity in agricultural applications.
Used in Fragrance and Flavor Industry:
2,3,5,6-Tetrafluoro-4-(trifluoromethyl)benzyl alcohol is utilized as a key intermediate in the production of fragrances and flavors. Its unique structure imparts distinct scents and tastes, making it valuable in the creation of novel and appealing products.
Used in Material Science:
Due to its potential applications in the development of new materials and chemical processes, 2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzyl alcohol is of interest in material science. Its unique properties can be harnessed to create innovative materials with improved performance characteristics.
Used in Chemical Process Development:
2,3,5,6-Tetrafluoro-4-(trifluoromethyl)benzyl alcohol is also used in the development of new chemical processes. Its unique structure and properties can be leveraged to improve the efficiency and selectivity of various chemical reactions, leading to the production of high-quality products with reduced environmental impact.

InChI:InChI=1/C8H3F7O/c1-16-7-5(11)3(9)2(8(13,14)15)4(10)6(7)12/h1H3

Upstream product

• 434-64-0 perfluorotoluene 
• 124-41-4 sodium methylate 
• 186581-53-3 diazomethane 
• 2787-79-3 4-Trifluoromethyl-2,3,5,6-tetrafluorophenol 
• 67-56-1 methanol 
• 2996-92-1 phenyl trimethylsiloxane 

Relevant academic research and scientific papers

A Key Intermediate in Copper-Mediated Arene Trifluoromethylation, [nBu4N][Cu(Ar)(CF3)3]: Synthesis, Characterization, and C(sp2)?CF3 Reductive Elimination

The synthesis, characterization, and C(sp2)?CF3 reductive elimination of stable aryl[tris(trifluoromethyl)]cuprate(III) complexes [nBu4N][Cu(Ar)(CF3)3] are described. Mechanistic investigations, including kinetic studies, studies of the effect of temperature, solvent, and the para substituent of the aryl group, as well as DFT calculations, suggest that the C(sp2)?CF3 reductive elimination proceeds through a concerted carbon–carbon bond-forming pathway.

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.

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).

Nucleophilic Displacement in Polyhalogenoaromatic Compounds. XIII Polyfluoroarene Systems

Rate coefficients are reported for the methoxydefluorination of decafluoro-biphenyl and -phenanthrene, of octafluoro-biphenylene, -naphthalene, -acenaphthylene, and -toluene, of 4H-heptafluorotoluene and the 4-bromo and 4-phenyl analogues, and of tetradecafluoro-4,4'-dimethylbiphenyl in methanol at 298 K.These rates are compared with theoretically calculated reactivities; none give perfect correlation.The orientation of nucleophilic attack upon polyfluorinated aromatic systems may be simply understood by considering each aromatic ring to act as a single entity and neglecting the effects of the carbon substituents, so that the orientation of attack of each benzene ring is the same as that of the corresponding polyfluorobenzene.

Quantitative estimation of the reactivity of perfluorinated methylbenzenes and benzocycloalkenes in nucleophilic substitution reactions

The kinetics of the reactions of perfluorinated xylenes, mesitylene, p-cymene, benzocycloalkenes (benzocyclobutene, indane, tetralin) and octafluoronaphthalene with sodium methoxide and piperidine have been studied.Rate constants of the reactions of perfluorinated aromatic compounds with sodium methoxide (taking into account one reaction centre) are shown to incease in the order: hexafluorobenzene perfluoro-p-xylene ca.= perfluoro-p-cymene octafluorotoluene ca.= perfluoro-m-xylene perfluoromesitylene ca.= perfluoro-o-xylene.In the reactions with piperidine, a different sequence was observed: hexafluorobenzene perfluoro-p-xylene perfluoro-p-cymene perfluoromesitylene perfluoro-m-xylene octafluorotoluene perfluoro-o-xylene.In the reactions of perfluorobenzocycloalkenes with sodium methoxide and piperidine, the reactivity grows by about a factor of 2 with increase of the perfluoroalicyclic ring size by one CF2-group, in the following order: perfluorobenzocyclobutene perfluoroindan perfluorotetralin.