335-65-9

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C8HF17/c9-1(10)2(11,12)3(13,14)4(15,16)5(17,18)6(19,20)7(21,22)8(23,24)25/h1H

Upstream product

• 423-53-0 1-chloro-1H,8H-hexadecafluoro-octane 
• 507-63-1 1-iodoheptadecafluorooctane 
• 647-29-0 n-perfluorooctanesulfinic acid 
• 591-50-4 iodobenzene 
• 52717-17-6 perfluorooctylcopper 
• 100-22-1 N,N,N',N'-tetramethyl-para-phenylenediamine 
• 2065-23-8 methyl 2-phenoxyacetate 
• 10544-63-5 ethyl crotonate 
• 423-55-2 1-perfluorooctyl bromide 
• 355-43-1 n-perfluorohexyl iodide 
• 62116-54-5 sodium diethyl methylmalonate 
• 106-47-8 4-chloro-aniline 
• 78-94-4 methyl vinyl ketone 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 307-33-5 1-Chloroperfluorooctane 
• 355-49-7 perfluorocetane 
• 133559-42-9 Fluorosulfuric acid heptadecafluorooctyl ester 
• 423-55-2 1-perfluorooctyl bromide 
• 307-34-6 Perfluorooctane 

Relevant academic research and scientific papers

On the preparation of 1H-perfluoroalkanes and a mechanism for the reduction of perfluoroalkyl iodides

1H-Perfluoroalkanes are prepared by sodium methoxide reduction of 1-iodoperfluoroalkanes.The experimental evidence indicates that the reaction proceeds either through a radical or a thermal mechanism.We have found that a high yield of 1H-perfluoroalkanes at complete conversion can be accomplished at atmospheric pressure using technology. - Keywords: 1H-Perfluoroalkanes; Methyl hypoiodide; Reduction; Mass spectrometry

Perfluoroalkylations and perfluorooxaalkylations. Part 3. Chloro-substituted diazines as substrates in copper-mediated cross-coupling

The (perfluoroalkyl)- and (perfluorooxaalkyl)diazines, 2,4-bis(perfluorooctyl)pyrimidine (3), 2,4,6-tris(perfluorooctyl)pyrimidine (6a), 2,4,6-tris(perfluoro-6-methyl-5-oxaheptyl)pyrimidine (6b), 3,6-bis(perfluorooctyl)pyridazine (10) and 2,6-bis(perfluorooctyl)pyrazine (13), have been prepared in good yield.This was accomplished by using chloro-substituted diazines as substrates in copper mediated cross-coupling reactions with perfluoroalkyl and perfluorooxaalkyl iodides.The yields of the cross-coupled products are influenced by the reaction conditions as well as by the structure of the fluoroaliphatic iodides and substrates. - Keywords: Perfluoroalkylations; Perfluorooxaalkylations; Chloro-substituted diazines; Cross-coupling; NMR spectroscopy; Mass spectrometry

Absolute rate constants for some reactions of perfluoro-n-alkyl radicals in solution

Absolute rate constants have been measured at 298 ± 2 K for some reactions of C2F5·, n-C3F7·, n-C7F15·, and n-C8F17· by time- resolved (laser flash photolysis) and competition kinetics. The last three of these radicals exhibit essentially equal reactivities, but C2F5· is somewhat more reactive. The strongly electrophilic nature of these radicals is illustrated by an outstanding Hammett correlation for the addition of n- C8F17· to four para-substituted styrenes, log(k(add)/(X)/k(add)/(H)) = - 0.53σ, (r) = 0.99 (X = p-CH3O to p-CF3), and, far more significantly, by a respectable correlation, (r) = 0.97, of log k(add) with the ionization potentials (IP) of 13 terminal olefins, the values of k(add) for n-C3F7· ranging from 1.6 x 106 to 2.2 x 106 M-1 s-1 for CH2=CHCN (IP = 10.91 eV) to 7.9 x 107 to 8.9 x 107 M-1 s-1 for α-methylstyrene (IP = 8.19 eV). The n-C8F17· radical is 100 times as reactive in hydrogen atom abstraction from tri-n-butyltin hydride as an n-alkyl radical, with k(abs)/(H) (n-C7F15·) = 2.0 x 108 M-1 s-1.

REACTIVITE COMPAREE DES PERFLUOROIODOALCANES (RFI) ET DES PERFLUOROALCOYL-2 IODO-1 ETHANES (RFCH2CH2I) EN PRESENCE DE COUPLE METALLIQUE ZINC-CUIVRE DANS UN SOLVANT DISSOCIANT PARTICULIER : LE SULFOLANE (RF = CnF2n+1, n pair)

Reactivity of perfluoroalkyl iodides (RFI) and perfluoroalkyl-2 iodide-1 ethanes (RFCH2CH2I), in the presence of a zinc-copper couple, in a particular dissociating solvent, "the sulfolane", is described.RFI and RFCH2CH2I react via an organometallic route to give perfluoroorganozinc compounds.Then, RFCH2CH2I react with the sulfolane solvent.In this case, a diperfluoroalkyl-2 ethyl-1 sulfone (RFCH2CH2)2SO2 is obtained.

Perfluoroalkylation of Benzene by 185 nm Photolysis of Perfluoroazooctane

Perfluoroazooctane was photolyzed in benzene upon low pressure Hg lamp irradiation to generate perfluorooctyl radicals, which reacted with an excess of benzene to afford perfluorooctylbenzene.The investigation on the wavelength and light intensity dependence revealed that this photolysis proceeded effectively upon 185 nm irradiation by two photon absorption.

Synthesis method of straight-chain perfluoroalkanes

The invention relates to a synthesis method of straight-chain perfluoroalkanes, which comprises the following steps: reaction of perfluoroalkyl iodine with alcohol solution of sodium alcohol at a certain temperature to purify 1-hydroperfluoroalkanes; reaction of 1-hydroperfluoroalkanes with fluorine gas at a certain temperature to purify straight-chain perfluoroalkanes. The synthesis method of theinvention has mild reaction conditions, high product yield, and is beneficial to cost saving. The process has low energy consumption, easy operation and is conducive to industrial production.

Benzophenone vs. Copper/Benzophenone in Light-Promoted Atom Transfer Radical Additions (ATRAs): Highly Effective Iodoperfluoroalkylation of Alkenes/Alkynes and Mechanistic Studies

Iodoperfluooralkylation of terminal alkenes and alkynes is effectively photo-promoted by benzophenone 2 (BP) or the photoreducible copper(II) complex 1. In particular, BP at 1 mol% in methanol upon 365 nm irradiation with a low-pressure mercury lamp (type TLC=thin layer chromatography, 6 W) results in a fast reaction with excellent reaction yields. Complex 1 and BP 2 exhibited very similar reactivity, suggesting that the reactions involving 1 are likely to be governed by the benzophenone photoactivation processes, rather than copper(I)/(II) redox processes. Mechanistic investigations using transient absorption spectroscopy revealed that a deactivation pathway of the benzophenone triplet (3BP*) is via its reaction with the methanol solvent. We propose that the generated radicals, in particular.CH2OH, play a key role in the initiation step forming Rf.by reacting with RfI, Rf.then entering a radical chain cycle.1H NMR studies provided evidence that a substantial amount (～7% NMR yield) of the hemiacetal CH3OCH2OH is formed, i.e., the possible by-product of the reaction between.CH2OH and RfI. Finally, DFT calculations indicate that a triplet-triplet energy transfer (TTET) process from3BP* to perfluorooctyl iodide (C8F17I) is unlikely or should be rather slow under the reaction conditions, consistent with the transient absorption studies. (Figure presented.).

An improved procedure for the synthesis of perfluoroalkylacetylenes

A new and easy way to synthesize acetylene compounds is proposed. This synthesis is improved by including in one-pot, three reactions in a single step, with good yields. The reactants are commonly used compounds.

Synthese de 3-perfluoroalkylprop-1-enes RF-CH2-CH=CH2

The reactions of perfluoroalkyl iodides with allylbromide or chloride, in the presence of solid potassium hydroxide KOH give 3-perfluoroalkylprop-1-enes RFCH2CH=CH2 in good yields under mild conditions. This reaction represents a synthetically viable and convenient route to such compounds.

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.