Perfluorohexyl iodide

FLUORINECOMPOUNDS,ORGANIC - FLUOROETHERS AND FLUORO AMINES] (Vol 11) Perfluorohexyl iodide [355-43-1]... 

Preparation of 2-(Peifluorohexyl)cyclohexanone from Perfluorohexyl Iodide 143]... 

N-Cyclohex-l-enylpyrrolidine (9 g 0 06 mol) was dissolved in pentane with A -ethyldiisopropylamine (7.8 g 0.06 mol). Perfluorohexyl iodide (13.4 g, 0.03 mol) IS added to the solution. Aprecipitate of A-ethyldiisopropylamine hydroiodide IS formed instantly After 3 h, the precipitate is filtered off, and the solution is evaporated The crude liquid is hydrolyzed with 6 mL of 40% sulfuric acid The mixture is stirred for 3 h and extracted with ether. The ether layer is neutralized with aqueous sodium hydrogen carbonate, washed with water, and dried over magnesium sulfate. The solvent is evaporated, and the residue is distilled. A second distillation with a spinning-band column yields 7 9 g (63%) of pure 2-(perfluoro-hexyl)cyclohexanone (bp, 71 -73 °C at 0 4 mm of Hg). 

Preparation of N-Butyl Perfluorohexylimidoyl Iodide from Perfluorohexyl Iodide [Ml]... 

On the small scale, no reaction occurred on boiling perfluorohexyl iodide in contact with metallic sodium. With 140 g of iodide and 7 g of sodium an explosion occurred after 30 min [6]. The temperature range for smooth interaction of bromobenzene, 1-bromobutane and sodium in ether to give butylbenzene is critical. Below 15°C reaction is delayed but later becomes vigorous, and above 30°C the reaction becomes violent [7]. Sodium wire and chlorobenzene react exothermally in benzene under nitrogen to give phenylsodium, and the reaction must be controlled by cooling. Use of... 

The coupling of /raaf-2,6-diodo-3,7-diphenyltetrathiafulvalene 704 (obtained in 62% yield by metallation of the corresponding diphenyl-TTF with LDA followed by iodination with perfluorohexyl iodide) with trimethylsilylacetylene in the presence of Pd(PPh3)4, Cul, and NEt3 in tetrahydrofuran (THF) afforded symmetrical bis(2-trimethylsilyl)ethynyl-TTF 705 in 70% yield which was then desilylated with aqueous KOFI to give 706 (Scheme 104) <1998S259>. 

The lithiated 7t-exTTF 924 was iodinated using perfluorohexyl iodide (PFHI) to give the iodo derivative 930. The latter took part in an Ullmann coupling using CuTC in l-methylpyrrolidin-2-one to afford the dimer 931 (Scheme 141) <2006CEJ2709>. 

Perfluorohexyl magnesium iodide, generated in situ from perfluorohexyl iodide and phenyl magnesium iodide, reacts with diethyl chlorophosphate in EtjO at -50°C to give diethyl perfluorohex-ylphosphonate in 56% yield (Scheme 3.37). ... 

The synthesis of 2,5-bis(perfluoroalkyl)thiophene using anionic peifluoroalkyla-tion is exemplified by the reaction of 2,5-dibromothiophene with perfluorohexyl iodide in the presence of copper." " ... 

Due to the availability of perfluoroalkyl iodides, this method quickly became the method of choice for the regioselective synthesis of perfluoroalkylated heterocycles. Chen and Tamborski used this reaction for the preparation of variety perfluoroalkyl-pyridines," azines," and triazines." For example, pyridines 72-73 and pyrimidine 74 were synthesized by addition of perfluorohexyl iodide to the agitated mixture of the corresponding heteroaryl bromide, cooper bronze powder in DMSO solvent under nitrogen at elevated temperature (Fig. 7.26)." ... 

Figure 7.26 Perfluoroalkylation of bromoheteroarenes using perfluorohexyl iodide.

Foral AX-E. See Hydrogenated rosin Foralkyl 16. See Perfluorohexyl iodide Forane 22. See Chlorodifluoromethane Forane 123. See Dichlorotrifluoroethane Forane 134a. See Tetrafluoroethane Forane 141b DGX, Forane 141b. See Dichlorofluoroethane... 

Hexane-1-thiol n-Hexanethiol Hexanethiol normal. See 1-Hexanethiol Hexane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodo-. See Perfluorohexyl iodide 1,2,6-Hexanetriol... 

Synonyms Perfluoro-n-hexyl sulfonic acid Empincal CeHFisOsS Formula CF3(CF2)sS03H Properties M.w. 400.11 Uses Fire extinguishant additives Perfluorohexyl iodide CAS 355-43-1 EINECS/ELINCS 206-586-6 Synonyms Hexane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodo- 1-lodoperfluorohexane 1-lodotridecafluorohexane Perfluoro-n-hexyl iodide Perfluoro-1-iodohexane Tridecafluorohexyl iodide Tridecafluoro-1-iodohexane 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluroo-6-iodohexane Empirical CeFisI Formula CF3(CF2)4CF2l Properties Colorless liq. which can turn rosy or violet sol. > 250 g/l in ethanol, acetone, ethyl acetate, xylene, hexane, tetrahydrofuran, dimethylformamide, dimethylsulfoxide, trichlorotrifluoroethane, chloroform insol. in water m.w. 445.95 sp.gr. 2.051-2.063 m.p. -45 C b.p. 

Perfluoro-n-hexyl sulfonic acid. See Perfluorohexanesulfonic acid Perfluoro-1-iodohexane. See Perfluorohexyl iodide... 

Tridac iSO 3. See lsotrideceth-3 Tridac iSO 6. See lsotrideceth-6 Tridac iSO 8. See lsotrideceth-8 Tridecafluorohexyl iodide Tridecafluoro-1-iodohexane. See Perfluorohexyl iodide (Tridecafluoro-1,1,2,2-tetrahydrooctyl) trichlorosilane. See (Tridecafluoro-1,1,2,2-tetrahydrooctyl)-1-trichlorosilane (Tridecafluoro-1,1,2,2-tetrahydrooctyl)-1-trichlorosilane... 

---