309-11-5

Usage

Uses

Used in Organic Chemical Reactions:
(Pentafluoroethyl)benzene is utilized as a solvent in various organic chemical reactions, providing a medium that facilitates the desired chemical transformations.
Used in Fluoroaromatic Compounds Production:
It serves as a precursor in the synthesis of a range of fluoroaromatic compounds, which are important for the development of new materials and pharmaceuticals.
Used in Pharmaceutical Manufacturing:
(Pentafluoroethyl)benzene is employed in the production of pharmaceuticals, where its unique properties contribute to the creation of novel drug molecules.
Used in Agrochemicals Production:
(Pentafluoroethyl)benzene is also used in the manufacturing of agrochemicals, which are essential for the development of effective pesticides and other agricultural products.
Used in Polymer Production:
(Pentafluoroethyl)benzene is involved in the production of polymers, which are used in a wide array of applications, from plastics to high-performance materials.
Used as an Intermediate in Fluorinated Materials Synthesis:
It acts as an intermediate in the synthesis of fluorinated materials, which are known for their unique properties, such as non-stick coatings and fire resistance.

Upstream product

• 5415-66-7 (2,2,2-trichloro-1,1-difluoro-ethyl)-benzene 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 108-86-1 bromobenzene 
• 2314-97-8 iodotrifluoromethane 
• 591-50-4 iodobenzene 
• 353-59-3 halon-1211 
• 354-64-3 Pentafluoroethyl iodide 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 71-43-2 benzene 
• 706-93-4 Phenylpentachloroethane 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 325810-07-9 tris(triphenylphosphane)(trifluoromethyl)copper(I) 
• 75-77-4 chloro-trimethyl-silane 
• 309-13-7 1-chloro-3-(pentafluoroethyl)benzene 

Downstream Products

• 656-84-8 1-nitro-3-(pentafluoroethyl)benzene 
• 729-83-9 3-Amino-4-sulfamoyl-1-pentafluorethyl-benzol 
• 729-84-0 3-Amino-1-pentafluorethyl-benzol-sulfonsaeure-⁽⁴⁾ 
• 654-58-0 4-amino-6-pentafluoroethyl-benzene-1,3-disulfonic acid diamide 
• 710-74-7 3-(perfluoroethyl)aniline 
• 2396-08-9 N,N-dimethyl-3-(pentafluoroethyl)aniline 

Relevant academic research and scientific papers

Pentafluoroethylation of Arenediazonium Tetrafluoroborates Using On-Site Generated Tetrafluoroethylene

Copper-mediated pentafluoroethylation of arenediazonium tetrafluoroborates with tetrafluoroethylene (TFE) on-site generated from TMSCF3 has been developed as a new method to prepare pentafluoroethyl arenes. The active pentafluoroethylation reagent “CuC2F5” is pre-generated from CuSCN, TFE and CsF, and its generation and further reaction are strongly solvent-dependent. This pentafluoroethylation reaction represents the first example of Sandmeyer-type pentafluoroethylation, which exhibits good functional group tolerance and potential applications for the synthesis of complicated bioactive compounds.

M?C Bond Homolysis in Coinage-Metal [M(CF3)4]? Derivatives

A comparative study of the homoleptic [M(CF3)4]? complexes of all three coinage metals (M=Cu, Ag, Au) reveals that homolytic M?C bond cleavage is favoured in every case upon excitation in the gas phase (CID-MS2). Homolysis also occurs in solution by photochemical excitation. Transfer of the photogenerated CF3. radicals to both aryl and alkyl carbon atoms was also confirmed. The observed behaviour was rationalized by considering the electronic structure of the involved species, which all show ligand-field inversion. Moreover, the homolytic pathway constitutes experimental evidence for the marked covalent character of the M?C bond. The relative stability of these M?C bonds was evaluated by energy-resolved mass spectrometry (ERMS) and follows the order CuAg?Au. The qualitatively similar and rather uniform behaviour experimentally observed for all three coinage metals gives no ground to suggest variation in the metal oxidation state along the group.

Visible-Light photoredox decarboxylation of perfluoroarene iodine(III) Trifluoroacetates for C-H trifluoromethylation of (Hetero)arenes

A scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C6F5I(OCOCF3)2 under photoredox catalysis has been developed. This method is tolerant of various (hetero)arenes and functional groups. Notably, C6F5I is recycled from the decarboxylation reaction and further used for the preparation of C6F5I(OCOCF3)2. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the application of trifluoroacetic acid in trifluoromethylation reactions.

CuI-Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl CuI Intermediate

The Cu(I)-catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC2F5, was isolated and its molecular structure confirmed by a single-crystal X-ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway.

TMSCF3 as a Convenient Source of CF2=CF2 for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation

A new method for the on-site preparation of tetrafluoroethylene (TFE) and a procedure for its efficient use in pentafluoroethylation by fluoride addition were developed by using a simple two-chamber system. The on-site preparation of TFE was accomplished by dimerization of difluorocarbene derived from (trifluoromethyl)trimethylsilane (TMSCF3) under mild conditions. Other fluoroalkylation reactions, such as (aryloxy)tetrafluoroethylation and tetrafluoroethylation processes, were also achieved using a similar approach. This work not only demonstrates a convenient and safe approach for the generation and use of TFE in academic laboratories, but also provides a new strategy for pentafluoroethylation.

The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η6-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me3SiRF and a fluoride ion source [Me4N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.

Stoichiometric and Catalytic Aryl-Perfluoroalkyl Coupling at Tri-tert-butylphosphine Palladium(II) Complexes

This Communication describes studies of Ph-RF (RF = CF3 or CF2CF3) coupling at Pd complexes of general structure (PtBu3)PdII(Ph)(RF). The CF3 analogue participates in fast Ph-CF3 coupling (II complex. Furthermore, they show that this undesired pathway can be circumvented by changing from a CF3 to a CF2CF3 ligand. Ultimately, the insights gained from stoichiometric studies enabled the identification of Pd(PtBu3)2 as a catalyst for the Pd-catalyzed cross-coupling of aryl bromides with TMSCF2CF3 to afford pentafluoroethylated arenes.

Pentafluoroethylating compositions

The present invention relates to pentafluoroethylating compositions, processes for obtaining them, and their use in pentafluoroethylation reactions.

PENTAFLUOROETHYLATING COMPOSITIONS

The present invention relates to pentafluoroethylating compositions, processes for obtaining them, and their use in pentafluoroethylation reactions.

Catalytic cycle for palladium-catalyzed decarbonylative trifluoromethylation using trifluoroacetic esters as the CF3 source

This paper demonstrates a catalytic cycle for Pd-catalyzed decarbonylative trifluoromethylation using trifluoroacetic esters as CF3 sources. The proposed cycle consists of four elementary steps: (1) oxidative addition of a trifluoroacetic ester to Pd0, (2) CO deinsertion from the resulting trifluoroacyl PdII complex, (3) transmetalation of a zinc aryl to PdII, and (4) aryl-CF3 bond-forming reductive elimination. The use of RuPhos as the supporting ligand enables each of these steps to proceed under mild conditions (3 sources.