56424-23-8

Usage

Uses

Used in Refrigeration Industry:
1-Phenyl-1,2,2,2-tetrafluoroethane, (1,2,2,2-Tetrafluoroethyl)benzene is used as a refrigerant for its thermodynamic properties that allow for efficient cooling and heating in various systems. Its non-flammable nature and low toxicity make it a safer alternative to other refrigerants.
Used in Aerosol Propellants:
In the aerosol industry, 1-Phenyl-1,2,2,2-tetrafluoroethane, (1,2,2,2-Tetrafluoroethyl)benzene serves as a propellant, enabling the dispensing of products such as personal care items, cleaning supplies, and other consumer goods from aerosol cans.
Environmental Considerations:
Despite its utility, 1-Phenyl-1,2,2,2-tetrafluoroethane, (1,2,2,2-Tetrafluoroethyl)benzene is recognized as a potent greenhouse gas with a high global warming potential. As a result, there is a growing focus on researching and adopting more environmentally friendly alternatives to mitigate its impact on climate change.

Upstream product

• 395-00-6 (E/Z)-1-chloro-1,2-difluoro-2-phenylethene 
• 13652-07-8 phenyltrifluorodiazoethane 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 13652-11-4 2,2,2‐trifluoro‐1‐phenylethan‐1‐one tosylhydrazone 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 116-15-4 perfluoropropylene 
• 101-81-5 Diphenylmethane 
• 135-98-8 sec-Butylbenzene 
• 538-93-2 1-phenyl-2-methylpropane 
• 98-82-8 Isopropylbenzene 

Downstream Products

• 447-14-3 1,2,2-trifluorostyrene 

Relevant academic research and scientific papers

Α, β, β-trifluorolactic of industrial manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: To provide a method of producing industrially α,β,β-trifluorostyrenes. SOLUTION: The method of producing industrially the α,β,β-trifluorostyrenes includes a dehydrofluorination step of reacting α-aryl-α,β,β,β-tetrafluoroethanes with an alkali metal-bis(trimethylsilyl) amide, in the production of α,β,β-trifluorostyrenes, and an after-treatment step executed followed thereto to react a mixture containing the α,β,β-trifluorostyrenes of objective products and bis-(trimethylsilyl) amine of a byproduct with hydrogen fluoride, or a salt or a complex comprising an organic base and hydrogen fluoride. COPYRIGHT: (C)2012,JPO&INPIT

Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes

Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [18F]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [18F]fluoride.

An efficient dehyrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β- difluorostyrenes and E-1-arylperfluoroalkenes

Dehydrofluorination of 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF 3) and 1-aryl-1-chloro-2,2,2-trifluoroethane (ArCHClCF3) using lithiumhexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) at room temperature produced 1,2,2-trifluorostyrene and 1-chloro-2,2-difluorostyrene, respectively, in very good isolated yields. Dehydrofluorination of 1,2,2,3,3,3-hexafluoro-1-phenyl-propane (PhCHFCF2CF3) and 1,2,2,3,3,4,4,4-octafluoro-1-phenyl-butane (PhCHFCF2CF 2CF3) using LHMDS produced the corresponding substituted olefins (1-phenyl-1,2,3,3,3-pentafluoroprop-1-ene and 1-phenyl-1,2,3,3,4,4,4- pentafluorobut-1-ene) in good yield and high E-selectivity. Dehydrofluorination of 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane (PhCHClCF2CF 3) and 1-chloro-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane (PhCHClCF2CF2CF3) produced a mixture of the corresponding E and Z olefins (PhCClCFCF3 and PhCClCFCF 2CF3) in good yield.

A highly efficient room temperature non-organometallic route for the synthesis of α,β,β-trifluorostyrenes by dehydrohalogenation

Various 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF3, Ar=phenyl, substituted phenyl, naphthyl, heteroaryl) were synthesized by the fluorination of the corresponding alcohols with DAST. Dehydrofluorination of ArCHFCF3 using lithium hexamethyldisilazide (LHMDS) base in THF at room temperature produced 1,2,2-trifluorostyrenes (ArCF=CF2) in 61-91% isolated yields. This procedure provides an excellent non-organometallic alternative to the generally used metallation-Pd(0) coupling methods.

Oxidative fluorination of S, Se and Te compounds

The synthesis and mechanism of formation of cis- and trans-Ph2SF4 is described. Starting compounds are Ph2S or Ph2SF2 and the oxidizing agent is XeF2 in the presence of Et4NCl. Also described is the synthesis of related chalcogen(IV and VI) fluorides such as t-butylSF3, difluorodibenzothiophene, PhSeF3, Ph2SeF2, PhSF5, p-MeC6H4SF5, PhSeF5, and PhTeF5. The reactions of Ph2S(O)F2 with alcohols and with the H2O-HF-glass system are briefly described.

Fluoro-olefin Chemistry. Part 18. Thermal Reaction of Hexafluoropropene with Diphenylmethane, Butylbenzenes, Benzyl Alcohol, and Benzyl Methyl Ether

The thermal reaction of hexafluoropropene with diphenylmethane gives the 1:1 adduct Ph2CHCF2CHFCF3 (4a) and the rearranged adduct PhCH2CF2CFPhCF3 (5a) via benzylic hydrogen abstraction.Analogous 1:1 adducts are formed from benzyl alcohol in low yield, i.e.PhCH(OH)CF2CHFCF3 (4e) and HOCH2CF2CFPhCF3 (5b), but the reaction is complicated by decomposition of the alcohol to benzaldehyde, toluene, and water followed by the formation of the toluene-hexafluoropropene adduct PhCH2CF2CHFCF3 (4c).A similar decomposition is observed with benzyl methyl ether and compound (4c) is the only fluorinated product isolated.With n-butylbenzene the 1:1 adduct PhCHPrnCF2CHFCF3 is formed in relatively low yield due to rearrangement of the intermediate radical PhCHPrnCF2C(*)FCF3 by a 1,5-hydrogen shift followed by β-scission to give the radical PhC(*)HCF2CHFCF3 and propene and hence (4c) and the cyclobutane (8a), respectively.With isobutylbenzene the only 1:1 adduct isolated is PhCH2CMe2CF2CHFCF3, although benzylic hydrogen abstraction does occur as shown by the formation of compounds (4c) and (8a). 1:1 Adducts are not detected in the products from the reaction with s-butylbenzene; the intermediate radical PhCMeEtCF2C(*)FCF3 undergoes (i) cyclisation to give the indan (12), (ii) decomposition to give the olefin CF2:CMeEt and the radical PhC(*)FCF3 and (iii) rearrangement followed by β-scission to give ethylene and the radical PhC(*)MeCF2CHFCF3.