34451-26-8

Usage

Uses

Used in Pharmaceutical Industry:
1H,1H,2H,2H-Perfluorooctanethiol is used as a reagent for the preparation of dinuclear arene ruthenium thiolato complexes with fluorous side-chains. These complexes exhibit significant antitumor activity, making them promising candidates for the development of novel cancer treatments.
Used in Neurodegenerative Disorder Treatment:
1H,1H,2H,2H-Perfluorooctanethiol is used as a reagent in the preparation of glycolipidic nitrones, which are potential antioxidant drugs for neurodegenerative disorders. These nitrones can help protect neurons from oxidative stress and may provide therapeutic benefits for conditions such as Alzheimer's disease, Parkinson's disease, and other related disorders.

InChI:InChI=1/C8H5F13S/c9-3(10,1-2-22)4(11,12)5(13,14)6(15,16)7(17,18)8(19,20)21/h22H,1-2H2

Upstream product

• 51740-38-6 toluene-4-sulfonic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl ester 
• 89889-20-3 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-9-iodononane 
• 80806-68-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol 
• 647-42-7 1H,1H,2H,2H-tridecafluoro-n-octanol 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 26650-09-9 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl thiocyanate 

Downstream Products

• 87851-83-0 benzyl(F-hexyl-2 ethyl) sulfure 
• 1474115-37-1 4-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)thio]phthalonitrile 
• 1474115-63-3 4,5-bis[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)thio]phthalonitrile 
• 552888-05-8 C₁₇H₁₁F₁₃O₄S 
• 1309763-37-8 5-{[2-(perfluorohexyl)ethyl]thiomethyl}-N-(2,4,6-trichlorophenyloxysulfonyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-carboxamide 
• 1309763-36-7 5-{[2-(perfluorohexyl)ethyl]thiomethyl}-N-(2,4,6-trimethylphenyloxysulfonyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-carboxamide 
• 87852-10-6 1-Phenyl-2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octane-1-sulfonyl)-ethanone 

Relevant academic research and scientific papers

Preparation method of perfluorohexylethyl sulfonate

The present invention relates to the technical field of fluorocarbon surfactants, and discloses a preparation method of perfluorohexylethyl sulfonate. The preparation method comprises: S1, dissolving sodium hydrosulfide in absolute ethyl alcohol, adding perfluorohexylethyl iodide and a catalyst, and carrying out a reaction under a heating condition to obtain perfluorohexyl ethanethiol; S2, blending perfluorohexyl ethanethiol and nitric acid, and reacting under a heating condition to obtain perfluorohexylethyl sulfonic acid; and S3, reacting the perfluorohexylethyl sulfonic acid with an alkali, purifying, and drying to obtain the perfluorohexylethyl sulfonate. According to the preparation method, perfluorohexylethyl iodide is used as a raw material, and absolute ethyl alcohol is used as a solvent. The method can reduce the production cost, digest production waste, and is safe, environment-friendly and simple to operate.

Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates

Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [(CnF2n+1(CH2)mSH); m/n = 3/4,6,8,10, 4a-d; m/n = 2/6, 8; m/n = 1/1,2,3,7,8H, 12a-e] was developed starting from commercially available fluorous alcohols (1a-d, 5, 9a-e). The intermediate (perfluoroalkyl)alkyl iodides and/or sulfonates were reacted with potassium thioacetate in DMF, and the resulting thioacetates were deacetylated by a Zemplén analogue reaction. The (perfluoroalkyl)alkane thiols were obtained in good overall yields and high purity.

FLUOROSILANES

Fluoroalkyl silanes are a class of compounds useful for various industrial purposes. For example, fluoroalkyl silanes which have hydrolysable groups (called hydrolysable fluoroalkyl silanes), are compounds useful as surface treatment agents which provide durable hydrophobic and oleophobic coatings. In general, hydrolysable fluoroalkyl silanes can be represented with the following formula: (RO—)3Si—RT wherein R is H or an alkyl; and RT is a monovalent organic compound terminated by a perfluoroalkyl group. When used to coat a surface, the (RO—)3 moiety reacts (via hydrolysis) with various chemical groups of the surface (e.g., hydroxyl, amine, or other reactive groups) thereby bonding the fluoroalkyl silane to the surface The RT moiety comprises a divalent organic linking group which links the silicon atom to a terminal group rich in fluorine atoms whose unique electronic properties impart desirable hydrophobic and oleophobic properties in a surface coating. Modification of the RT moiety is useful in the engineering of fluoroalkyl silanes. The present invention provides for fluoroalkyl silanes having RT moieties which have not been heretofore considered.

SULFUR CONTAINING FLUOROALKYL AMINES AND ISOCYANATES

The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems previously known methods. Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents. Furthermore, unlike previously known methods, the method of the present invention can produce oxidized forms of sulfur containing fluoroalkyl amines wherein the sulfur atom thereof is oxidized.

Novel fluorinated amphiphilic cyclodextrin derivatives: Synthesis of mono-, di- and heptakis-(6-deoxy-6-perfluoroalkylthio)-β-cyclodextrins

A new series of fluorinated amphiphilic β-cyclodextrin derivatives has been synthesized. The strategy is based on the modification of the C-6 position of the mono-6-deoxy-6A-para-tolylsulfonyl, di-6A, 6D-deoxy-6A, 6D-(para-tolylsulfonyl) and heptakis-(6-deoxy-6-iodo)-β-cyclodextrin precursors. The synthesis lead to mono-perfluoroalkylthio-, di-perfluoroalkylthio- and heptakis-perfluoroalkylthio-β-cyclodextrin in excellent yields (90-99%).

Synthesis of terminally perfluorinated long-chain alkanethiols, sulfides and disulfides from the corresponding halides

Semifluorinated n-alkanethiols, symmetrical sulfides and disulfides bearing the chain(s) F(CF2)n(CH2)m with n=4, 6, 8, 10, and m=2, 11 have been prepared by various synthetic methods, starting from the corresponding iodides or bromides. Methods based on sodium hydrogen sulfide, commonly used to accomplish this conversion, treatment of the Bunte salt obtained from sodium thiosulfate, the basic hydrolysis of isothiouronium salts, the hydrolysis under mild conditions of thiophosphorates formed from sodium thiophosphate and the basic hydrolysis of thiol acetic acid derivatives, have been investigated and compared relatively to the selective synthesis of the title compounds. The thiolacetic route yields essentially the thiols with some amounts of disulfides. Results from thiourea appears similar. Sodium thiophosphate constitutes an excellent route for the synthesis of thioethers, particularly when starting from the bromides. The two classical methods based on sodium hydrogen sulfide and sodium thiosulfate exhibit poor selectivity. It has been possible to obtain all the sulfur compounds reported in the pure state.

Catalytic hydrogenolysis of organic thiocyanates and disulfides to thiols

A process for the preparation of a thiol comprising reacting hydrogen with a thiocyanate or disulfide wherein the reaction with thiocyanate is conducted in the presence of a catalyst comprising a Group VIII metal or a mixture thereof; and the reaction with thiocyanate or with disulfide is conducted in the presence of a catalyst comprising a Group VIII metal or mixture thereof in the presence of a modifier metal selected from a group consisting of Group IB, Group IIB, Group IIIA, Group IVA, Group VA and Group VIA metal or mixture thereof, said catalyst being on a porous insoluble support.

Free-radical addition of 2-(perfluoroalkyl)ethanethiols to alkenes, alkadienes, cycloalkenes, alkynes and vinyl monomers

The free-radical addition of 2-(perfluoroalkyl)ethanethiols (RFCH2CH2SH) to alkenes, cycloalkenes, alkadienes and alkynes has been studied to determine: (1) the mode of reaction, i.e. the stereochemistry, regiochemistry and any skeletal changes: (2) the relative reactivity towards unsaturates of differing structures and classes as affected by the presence of the RF group; and (3) the influence of the reaction conditions on the rate of addition or selectivity for different products.Adducts from 2-(F-hexyl)ethanethiol (1) and alkenes have been obtained in high yield,but containing small amounts of regio isomers.For example compound 1 with 1-heptene gave 1-heptane (3, 96percent yield) as well as 2-heptane (4, O.61percent) and 3-heptane (5, 2.22percent). 1,6-Hexadiene and 1,7-octadiene gave chiefly linear adducts, i.e.RFCH2CH2S(CH2)nCH=CH2 (7, n=4; or 12, n=6, respectively) and RFCH2CH2S(CH2)nSCH2CH2RF (8, n=6; or 14, n=8, respectively).A small amount (2-3percent) of cis- and trans-1-methyl-cyclohexane (13) isomers were present in 12.Compound 1 with 1,6-heptadiene gave 7--1-heptene (9), the bis adduct, 1,7-bis-heptane (11) and the cyclic adducts, cis- and trans-1-methal-2-methylcyclopentane (10).The relative amounts of cyclic isomers depended on the reactant ratio.Compound 1 added readily with free-radical initiation to vinyl monomers such as styrene and vinyl acetate, and to phenyl acetylene, propargyl acetate and ethyl propynoate.These new addition products are useful as models for further study.

2-(2-hydroxy-3-perfluoroalkyl thiomethyl-5-alkylphenyl)2H-benzotriazoles and stabilized compositions thereof

2-(2-Hydroxy-3-perfluoroalkylthiomethyl-5-alkylphenyl)-2H-benzotriazoles are prepared by reacting the Mannich base hydrohalide or quaternary salt of a 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazole with a perfluoroalkyl mercaptan. The products exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.

FONTIONNALISATION DES IODURES DE F-ALKYL-2 ETHANE PAR CATALYSE PAR TRANSFERT DE PHASE: IMPORTANCE DE CETTE TECHNIQUE EN SERIE F-ALKYLEE

F-alkyl-2 ethane iodides are very important starting materials in the field of organic chemistry.Their reactivity in homogeneous medium shows some drawbacks: reactions are uncomplete and resulting compounds are not pure.We resolved these problems using phase transfer catalysis and obtained outstanding results.F-alkyl-2 ethane iodides are strongly hydrophobic; so organic solvents are not necessary (water was used) and moreover the emulsions promoted during the reaction are not stable.