65440-93-9

Usage

Uses

Used in Surfactant Industry:
(PERFLUOROHEXYL)BENZENE is used as a surfactant for its ability to reduce surface tension, which aids in the spreading and wetting of liquids on surfaces.
Used in Lubricant Industry:
(PERFLUOROHEXYL)BENZENE is used as a lubricant due to its low friction coefficient, which helps in reducing wear and tear in mechanical systems.
Used in Industrial Applications:
(PERFLUOROHEXYL)BENZENE is used in various industrial applications, taking advantage of its high thermal and chemical stability, as well as its water and oil repellency.
Used in Production of Fluorinated Polymers and Coatings:
(PERFLUOROHEXYL)BENZENE is used as a precursor in the production of fluorinated polymers and coatings, which are valued for their durability and resistance to environmental factors.
Used in Electronics Industry:
(PERFLUOROHEXYL)BENZENE is used in the electronics industry for its properties that contribute to the performance and reliability of electronic components.
Used in Textile Industry:
(PERFLUOROHEXYL)BENZENE is used in the textile industry to provide water and oil repellency to fabrics, enhancing their durability and ease of maintenance.
Used in Medical Imaging Applications:
(PERFLUOROHEXYL)BENZENE is used in medical imaging applications, such as in the development of contrast agents for imaging techniques that require specific properties like stability and low toxicity.
Environmental and Health Concerns:
However, (PERFLUOROHEXYL)BENZENE and other perand polyfluoroalkyl substances (PFAS) have raised environmental and health concerns due to their persistence, potential bioaccumulation, and toxicity. Their use and environmental impact are currently being regulated and investigated.

Upstream product

• 100-42-5 styrene 
• 55591-23-6 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl chloride 
• 592-76-7 1-Heptene 
• 1073-67-2 4-vinylbenzyl chloride 
• 592-41-6 1-hexene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 591-50-4 iodobenzene 
• 353-59-3 halon-1211 
• 111-66-0 oct-1-ene 
• 79-46-9 2-nitropropane 
• 355-43-1 n-perfluorohexyl iodide 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 105-38-4 vinyl propionate 
• 769-78-8 vinyl benzoate 

Downstream Products

• 751452-11-6 3-perfluorohexylbenzenesulfonic acid 

Relevant academic research and scientific papers

Aromatic perfluoroalkylation with metal complexes in electrocatalytic conditions

A one-step catalytic method for aromatic perfluoroalkylation with electrochemically reduced metal complexes under mild conditions with decisive role of the sacrificial anode metal ion has been developed. Cross-coupling is successful with bromo- and iodo-benzene and perfluoroalkyl iodide and number of cobalt and nickel complexes.

Towards a practical perfluoroalkylation of (hetero)arenes with perfluoroalkyl bromides using cobalt nanocatalysts

A convenient methodology for perfluoroalkylation including trifluoromethylation of (hetero)arenes with perfluoroalkyl bromides was developed. Key for the success is the use of a specific cobalt-based nanocatalyst, which can be recycled at least up to 4 times. The scope of this first cobalt-catalyzed perfluoroalkylation is presented and detailed catalyst characterization (e.g. analytical STEM, XPS, and XRD) has been carried out.

Use of Nitrogen-Doped Carbon Nanodots for the Photocatalytic Fluoroalkylation of Organic Compounds

The use of amine-rich N-doped carbon nanodots (NCNDs) for the photochemical radical perfluoroalkylation of organic compounds is reported. This operationally simple approach occurs under mild conditions producing valuable new C?C bonds. The chemistry is dr

METHOD FOR PREPARATION OF FLUORO, CHLORO AND FLUOROCHLORO ALKYLATED COMPOUNDS BY HOMOGENEOUS CATALYSIS

The invention discloses a method for preparation of fluoro, chloro and fluorochloro alkylated compounds by homogeneous Pd catalyzed fluoro, chloro and fluorochloro alkylation with fluoro, chloro and fluorochloroalkyl halides in the presence of di(1-adamantyl)-n-butylphosphine and in the presence of 2,2,6,6-tetramethylpiperidine 1-oxyl.

Single-stage synthetic route to perfluoroalkylated arenes via electrocatalytic cross-coupling of organic halides using Co and Ni complexes

A new method of single-stage synthesis of perfluoroalkylated arenes via cross-coupling of bromo (in some cases, chloro) arenes and heteroarenes (derivatives of benzene, pyridine and furan) and organic perfluoroalkyl halides involving complexes of nickel and cobalt in low oxidation state with α-diimines under mild conditions was proposed. Perfluoroalkylated products are obtained in good yields in the presence of М(I)L (M?=?Ni, Co) catalyst (1–10%) electrochemically generated from M(II)L at room temperature without chemical reductant. It has been found that success of the catalytic process is dependent on the reduction potential of the catalyst. The more negative reduction potential is, the more effective is the catalyst.

Iron-catalyzed electrochemical C-H perfluoroalkylation of arenes

A new iron-catalyzed reaction for the coupling of perfluoroalkyl iodides (RFI) with aromatic substrates is described. The perfluoroalkylated arene products are obtained in good to excellent yields in the presence of a [(bpy)Fe(ii)] catalyst (10

Palladium-catalyzed C-H perfluoroalkylation of arenes

A new Pd-catalyzed reaction for the coupling between perfluoroalkyl iodides (RFI) and simple aromatic substrates is described. The perfluoroalkylated arene products are obtained in good to excellent yields in the presence of a phosphine-ligated Pd catalyst and Cs2CO3 as a base. The development, optimization, scope, and preliminary mechanistic studies of these transformations are reported.

Redox system for perfluoroalkylation of arenes and α-methylstyrene derivatives using titanium oxide as photocatalyst

Photoirradiation of titanium oxide (TiO2) excites the electrons from the valence band to the conduction band, leaving holes in the valence band. Using these holes and electrons, it is possible to perform one-electron oxidations and reductions. We developed a method for the photocatalytic perfluoroalkylation of aromatic rings such as benzene and its derivatives, naphthalene and benzofuran with perfluoroalkyl iodide by the combination of reduction and oxidation reactions with TiO2. Perfluoroalkyl iodide was reduced to a perfluoroalkyl radical by the excited electrons in the conduction band of TiO2, and the resulting radical reacted with an aromatic ring to form an arenium radical that was successively oxidized to a cation by the holes in the valence band of TiO2. Similarly, the photocatalytic reaction of α-methylstyrene with perfluoroalkyl iodide afforded perfluoroalkylated α-methylstyrene, in which the perfluoroalkyl group is on a methyl carbon.

Bipyridinium ionic liquid-promoted cross-coupling reactions between perfluoroalkyl or pentafluorophenyl halides and aryl iodides

(Chemical Equation Presented) A new room-temperature ionic liquid has been synthesized from 2,2′-bipyridine. This liquid improved the copper-catalyzed cross-coupling reactions between perfluoroalkyl or pentafluorophenyl halides and aryl iodides. Good recyclability using this solvent system was observed.

Direct Perfluoroalkylation of Aromatic and Heteroaromatic Compounds with Perfluoroalkanesulfonyl Chlorides Catalysed by a Ruthenium(II) Phosphine Complex

The perfluoroalkylation of aromatic and heteroaromatic compounds by perfluoroalkanesulfonyl chlorides 1 has been investigated in the presence of a ruthenium(II) phosphine complex.The reaction of compounds 1 with substituted benzenes or thiophenes proceeded smoothly with extrusion of sulfur dioxide at 120 deg C to give corresponding perfluoroalkylated compounds in good yield.No expected perfluoroalkylated product was obtained in the reaction of compounds 1 with pyrrole; however, 1-trimethylsilyl- and 1-triisopropylsilyl-pyrrole were regioselectively perfluoroalkylated at their 2- and 3-position, respectively.