307-99-3

Usage

Uses

Used in Chemical Industry:
1H,8H-PERFLUOROOCTANE is used as a fluorinated solvent for the production of fluorinated polymers, which are valued for their exceptional chemical resistance, thermal stability, and non-stick properties. These polymers find applications in various sectors, including aerospace, automotive, and electronics.
Used in Coatings Industry:
In the coatings industry, 1H,8H-PERFLUOROOCTANE serves as a component in the formulation of high-performance coatings. These coatings are known for their durability, resistance to environmental factors, and low-friction characteristics, making them suitable for use in industrial and marine applications.
Used in Electronics Industry:
1H,8H-PERFLUOROOCTANE is utilized in the electronics industry as a solvent for the manufacturing of electronic components and devices. Its properties contribute to the enhanced performance and reliability of these components, particularly in harsh environmental conditions.
Used in Medical Imaging:
1H,8H-PERFLUOROOCTANE is used as a contrast agent in medical imaging, specifically in the field of ophthalmology. It is employed for retinal imaging, where its unique properties allow for improved visualization and diagnosis of various retinal conditions.
Used in Research and Development:
Due to its highly fluorinated structure, 1H,8H-PERFLUOROOCTANE is also used in research and development for the exploration of new materials and applications. Its chemical properties make it a valuable compound for studying the effects of fluorination on the behavior of organic compounds and their potential uses in various fields.

InChI:InChI=1/C8H2F16/c9-1(10)3(13,14)5(17,18)7(21,22)8(23,24)6(19,20)4(15,16)2(11)12/h1-2H

Upstream product

• 376-18-1 1H,1H,9H-hexadecafluoro-1-nonanol 
• 376-71-6 2,2,3,3,4,4,5,5-octafluoropentanoyl chloride 
• 376-72-7 2,2,3,3,4,4,5,5-octafluorovaleric acid 
• 813-03-6 5-Hydro-octafluor-valerylfluorid 
• 375-50-8 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane 
• 76-21-1 9H-hexadecafluorononanoic acid 
• 308-35-0 C₁₀H₂F₁₆O₄ 
• 335-70-6 1,8-diiodoperfluorooctane 
• 68-12-2 N,N-dimethyl-formamide 
• 423-53-0 1-chloro-1H,8H-hexadecafluoro-octane 
• 16486-98-9 1-chloro-1H,8H-hexadecafluoro-8-iodo-octane 
• 812-58-8 1,8-dibromoperfluorooctane 

Downstream Products

• 1310492-30-8 diethyl 2,2'-(perfluorooctane-1,8-diyl)dibenzoate 

Relevant academic research and scientific papers

Studies on polyhaloalkanes. V. A new reduction system: zinc/hydrazine hydrate

Using zinc/hydrazine hydrate as a new reduction system, polyfluoroalkyl halides such as Cl(CF2)nH (1a-c, n = 4, 6, 8), Cl(CF2)nI (1e-g, n = 4, 6, 8) and R(CF2)nCl (n = 4, 6, 1h,i) have been converted to the corresponding reduction products H(CF2)nH (2a-g, n = 4, 6, 8) and R(CF2)nH (n = 4, 6, 2h,i) in high yield.Reduction of the CF2Cl group was faster than that of the CHI in the reaction of 1m. - Keywords: Polyhaloalkanes; Reduction; Zinc/hydrazine hydrate system; NMR spectroscopy; Mass spectrometry

Organofluorine compounds and fluorinating agents part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates 1, 2

The homologous 1-iodo-perfluoroalkanes 1a-1c and α,ω-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Horner olefination assisted by ultrasound and in non-conventional acetalations of methyl α-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-α-L-altropyranosides 10, 11, 13, and 14 were obtained.

Method for preparing α-substituted ω-hydroperfluoroalkanes

A method for the preparation of α-substituted ω-dihydroperluoroalkane derivatives of the general formula H(CF2 CF2)n R wherein R=H or COOH, and n=1-10 is characterized by oxidizing α, α, ω-trihydroperfluoroalcohols with an oxygen gas or an oxygen-containing gas in the presence of a homogeneous copper catalyst and an alkaline agent in an organic solvent with subsequent isolation of the desired product.

A novel synthesis of per(poly)fluoroalkyl aldehydes

A novel synthesis of per(poly)fluoroalkyl aldehydes in high yield by the reaction of per(poly)fluoroalkyl iodides or bromides with dimethylformamide initiated by a PbBr2(catalyst)/Al bimetal redox system is described.

SOLVENT EFFECTS IN BETWEEN PERFLUOROALKYLIODIDES AND CADMIUM

The interaction between perfluoroorgano iodides (RfI where Rf = F(CF3)2C(CF2CF2)3, n-C6F13, n-C8F17, F(CF3)2COCF2CF2, F(CF3)2CO(CF2CF2)4 and C2H5OC(O)(CF2CF2)2OCF2CF2) with cadmium in an acetonitrile solvent media produces primarily the coupled products (RfRf, 72-90percent yield) in addition to minor quantities of the reduction products (RfH).On the other hand ICF2CF2I and ClCF2CFClI, by a 1,2-dehalogenation reaction, from the olefins CF2=CF2 and CF2=CFCl, respectively, as the principal products.The interaction of RfI compounds with cadmium in other solvent media, e.g. diethyl ether, tetrahydrofuran (YHF)), N,N-dimethylformamide (DMF), and bis(2-methoxyethyl)ether(diglyme) were examined and found to produce a different ratio of RfRf and RfH products.

Thermal Decomposition of Some Perfluoro- and Polyfluorodiacyl Peroxides

Seven polyfluoroacyl peroxides were synthesized, some of them by a new procedure involving the direct interaction of an acyl fluoride with hydrogen peroxide.In the temperature range of 20-40 deg C, all these peroxides undergo first-order decomposition in dilute 1,1,2-trichloro-1,2,2-trifluoroethane (Freon-113) solutions (F-RF.Differing from other perfluoro or polyfluoro radicals, the perfluoro-α-isopropoxyethyl radicals (10) undergo substantial β scission to form perfluoroisopropyl radicals (11) during their lifetime.The ΔHexc. values for the perfluoroacyl peroxides are about 24 kcal mol-1, or about 5 kcal lower than that of the nonfluorinated diacyl peroxides (ca. 29 kcal mol-1).Apparently, the higher relative rates for 3 and 7 are caused by different factors.The latter peroxide (7) decomposes with a more favorable ΔSexc. term, whereas the former (3) decomposes with lower values of both ΔHexc. and ΔSexc..Thus, weakening of the peroxide bond by H bonding of the peroxide oxygen atom with the acidic ω-hydrogen atom seems to be implicated in the decomposition of 3.With a half-life of 81 min at 20 deg C, 3 may become a useful low-temperature initiator for free-radical reactions and polymerization.

Conformational energies of perfluoroalkanes. 5. Dipole moments of H(CF2)nH and H(CF2)nI

Dielectric and refractive index increments at 25°C are reported for some α,ω-dihydroperfluoroalkanes and α-hydro-ω-iodoperfluoroalkanes in benzene and CCl4. Similar measurements on perfluorocyclohexane and perfluoro-n-hexane are used to deduce effective atomic polarizations for fluorocarbons in solution. The dipole moments obtained lead to a somewhat smaller characteristic ratio for the perfluoroalkane chain than had earlier been estimated by Bates and Stockmayer.