80806-68-4

Usage

Uses

Used in the Chemical Industry:
3-(Perfluorohexyl)propanol is used as a precursor in the synthesis of fluoroalkyl vinyl ethers for [application reason]. The reaction of this fluorinated alcohol with divinyl ether and/or trivinyl ether allows for the creation of valuable intermediates that can be further utilized in the production of a range of fluorinated compounds with diverse applications.
Used in the Production of Fluoroalkyl Vinyl Ethers:
3-(Perfluorohexyl)propanol is used as a key component in the preparation of fluoroalkyl vinyl ethers, which are important in the synthesis of various fluorinated polymers and materials. These ethers can be used to create polymers with improved properties, such as increased thermal stability, chemical resistance, and non-stick characteristics, which are valuable in industries like automotive, aerospace, and electronics.

InChI:InChI=1/C9H7F13O/c10-4(11,2-1-3-23)5(12,13)6(14,15)7(16,17)8(18,19)9(20,21)22/h23H,1-3H2

Upstream product

• 83311-03-9 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 
• 89889-20-3 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-9-iodononane 
• 355-43-1 n-perfluorohexyl iodide 
• 107-18-6 allyl alcohol 
• 38550-44-6 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-iodononan-1-ol 
• 80793-18-6 3-(perfluorohexyl)prop-1-ene 
• 60023-26-9 Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate 
• 165281-74-3 Ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoate 
• 67-56-1 methanol 
• 25291-17-2 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene 
• 83310-90-1 2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 

Downstream Products

• 83311-03-9 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 
• 89889-20-3 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-9-iodononane 
• 27854-30-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoic acid 
• 228570-06-7 toluene-4-sulfonic acid 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl ester 
• 910660-79-6 benzyl-bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-amine 
• 910660-90-1 bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester 
• 910660-96-7 Bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-((2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester 
• 110980-12-6 Methyl 3-perfluorohexyl-propyl (-)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate 
• 162082-62-4 3-(perfluorohexyl)propyl triflate 
• 1245062-17-2 3-(perfluorohexyl)propyl 4-(2-propenyloxy)benzoate 
• 1331781-75-9 3-(perfluorohexyl)propyl 4-(3-acryloyloxypropyloxy)benzoate 
• 1245062-18-3 3-(perfluorohexyl)propyl 4-(3-hydroxypropyloxy)benzoate 
• 34451-26-8 2-perfluorohexylethanethiol 
• 1315274-04-4 C₂₈H₂₄F₂₆O₃ 

Relevant academic research and scientific papers

A telechelic fluorinated diol from 1,6-diiodoperfluorohexane

The radical addition of 1-iodoperfluorohexane (1) to allyl alcohol (2-propen-1-ol) (2) was investigated in the presence of various initiating systems (photochemically or in the presence of redox catalysts or organic initiators), leading to C6F13CH2CHICH2OH (3) in various yields. A scale of efficiency of the involved radical system was proposed, triphenylphosphine and AIBN yielding the best conversions of 1. Interestingly, AIBN, when added three times in the course of the reaction was the most suitable for an almost quantitative consumption of 1. Then, 3 was reduced to C6F13C3H6OH (4) in high yields by tributylstannane. Such a two-step procedure was extrapolated to the preparation of the fluorinated telechelic diol from 1,6-diiodoperfluorohexane (5). First, the formations of both the 1-to-1 monoadduct (6) and 1-to-2 α,ω-diadduct (7) were noted and discussed: optimised conditions enabled production of 7 in 81% yield with a complete conversion of 5. Then, telechelic diol HOC3H6C6F12 C3H6OH (8) was synthesised selectively in 88% yield, from the reduction of the iodine atoms of 7 by tributylstannane. 1H, 19F and 13C NMR spectroscopies allowed characterisation of all the intermediates and products without ambiguity.

A fluorous ethylenediamine promoted direct C-H arylation of unactivated arenes with aryl halides

A novel and recyclable fluorous ethylenediamine was prepared. Together with potassium tert-butoxide, the fluorous ethylenediamine showed a good activity in promoting the coupling of aryl halides with benzene derivatives without the aid of transition-metal catalysts. Furthermore, a chain homolytic aromatic substitution mechanism was proposed in this paper.

Probing the limitations of the fluorous content for tag-mediated microarray formation

The synthesis of a di-perfluorohexyl tag is reported for use in a fluorous-based carbohydrate microarray. A comparative microarray study with this di-perfluorohexyl tag and a mono-perfluorooctyl and mono-perfluorohexyl tag found the increased fluorous content conducive to better spot morphology and easier washing protocols without precluding reuse of the fluorous slide.

Mesophase structure of low-wetting liquid crystalline polyacrylates with new perfluoroalkyl benzoate side groups

The synthesis, thermal behavior, bulk microstructure, and wettability of new polyacrylates carrying spaced 4-perfluorohexylpropyl benzoate and 4-perfluorooctylpropyl benzoate units in the side groups were Investigated. X-ray diffraction analysis proved the formation of different smectic mesophases (SmI2, SmF2, and SmC2) and the evolution of their structures and lattice parameters with temperature. The mesophase polymorphic behavior depended on the length of the perfluorinated chain segment in the repeat unit. The electron density profiles along the smectic layer normal were drawn and provided a deeper insight into the packing of the side chains in a tilted, double layer structure. Thin polymer films were cast from solution, and their low wettability was established by measurements of contact angles with different probing liquids. We suggest that the hydrophobicity and lipophobicity of the films are enhanced by the mesophase surface structure which is mediated by the high-order, mesophase bulk structure.

Cyclic peptide facial amphiphile preprogrammed to self-assemble into bioactive peptide capsules

(Figure Presented) Programmed assembly: A unique supramolecular building block, a cyclic peptide facial amphiphile, predestined to self-assemble into a nanocapsule structure, has been developed (see figure). This general strategy will allow the easy construction of a variety of bioactive nanocapsules.

3-(Perfluoroalkyl)propanols: Valuable building blocks for fluorous chemistry

2-Iodo-3-(perfluoroalkyl)propanols are obtained in excellent yields and several-hundred-gram quantities by the controlled radical addition of commercially available n-perfluoroalkyl and perfluoroisoalkyl iodides to allyl alcohol. Their consecutive reduction with hydrazine hydrate and Raney nickel catalyst in methanol afforded the corresponding 3-(perfluoroalkyl)propanols in high yields and purity. Georg Thieme Verlag Stuttgart.

Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols

N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.

Process for producing a polyfluoroalkyl (meth)acrylate

A process for producing a polyfluoroalkyl (meth)acrylate, which comprises isolating, from a reaction mixture containing a polyfluoroalkyl (meth)acrylate obtained by reacting a polyfluoroalkyl iodide of the formula CnF2n+1(CH2)mI (wherein n is an integer of from 2 to 7, and m is an integer of from 1 to 4) with a metal (meth)acrylate in tert-butanol, said polyfluoroalkyl (meth)acrylate by the following steps (1) to (3):(1) a step of taking out a crude liquid from the reaction mixture by solid-liquid separation;(2) a step of distilling the crude liquid to separate it into compound group A of compounds having a lower boiling point than the polyfluoroalkyl (meth)acrylate and compound group B of the polyfluoroalkyl (meth)acrylate and compounds having a higher boiling point than the polyfluoroalkyl (meth)acrylate; and(3) a step of distilling and purifying the polyfluoroalkyl (meth)acrylate from the compound group B in the presence of a polymerization inhibitor.

Synthesis and 19F NMR study of RF-oleic acid-F13

A seven-step synthesis of Z-13,13,14,14,15,15,16,16,17,17,18,18, 18-tridecafluoro-octadec-9-enoic acid (oleic acid-F13) is reported. The key step is a Wittig reaction to form the C9-C10 double bond with a Z:E isomeric ratio greater than 20:1. The 19F nuclear magnetic resonance (NMR) spectrum is included and unambiguous assignments have been made with the aid of 19F-19F correlation NMR spectroscopy (COSY spectra).

Selective mono- and di{(perfluoroalkyl)acylation} of ferrocene

The selective synthesis of mono- and 1,1′-di{(perfluoroalkyl)acylated} ferrocenes by Friedel-Crafts acylation with (perfluoroalkyl)acyl halides is described. The acyl derivatives were further converted to the corresponding (perfluoroalkyl)alkyl ferrocenes by reduction of the carbonyl group with LiAlH4/AlCl3. Electrochemical studies of all the obtained substituted ferrocenes were carried out to assess the influence of the perfluoroalkyl ponytails on their redox behavior.