200112-75-0

Usage

Uses

Used in Chemical Synthesis:
3-(Perfluorooctyl)propyl iodide is used as a building block for the preparation of fluoroalkylalkylthiols through Zemplen deacylation. This application takes advantage of its perfluoroalkyl group, which can be further modified or utilized in the synthesis of more complex molecules.
Used in Oligosaccharide Synthesis:
In the field of automated fluorous-assisted solution-phase oligosaccharide synthesis, 3-(Perfluorooctyl)propyl iodide is used as an activator for thioglycoside donors. Its role in this process is to facilitate the formation of glycosidic bonds, which are essential for the construction of oligosaccharides, important molecules in various biological processes and potential therapeutic targets.
Used in Pharmaceutical Industry:
3-(Perfluorooctyl)propyl iodide may also find applications in the pharmaceutical industry, where its unique properties can be harnessed for the development of novel drugs or drug delivery systems. The perfluoroalkyl group can potentially enhance the solubility, stability, or targeting of drug molecules, making it a valuable component in the design of new therapeutic agents.
Used in Material Science:
The perfluorinated nature of 3-(Perfluorooctyl)propyl iodide may also make it suitable for applications in material science, where its hydrophobic and non-stick properties could be utilized in the development of coatings, lubricants, or other specialized materials with unique properties.

InChI:InChI=1/C11H6F17I/c12-4(13,2-1-3-29)5(14,15)6(16,17)7(18,19)8(20,21)9(22,23)10(24,25)11(26,27)28/h1-3H2

Upstream product

• 1651-41-8 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecan-1-ol 
• 507-63-1 1-iodoheptadecafluorooctane 
• 38550-45-7 3-perfluoro-n-octyl-2-iodo-1-propanol 

Downstream Products

• 139175-50-1 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecan-1-amine 
• 494798-73-1 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)-benzaldehyde 
• 1039136-82-7 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl (E)-3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate 
• 1039136-81-6 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl (E)-3,3,3-trifluoro-2-(4-methoxyphenylimino)propanoate 
• 17002-69-6 C₁₅H₁₈F₁₇N₃ 
• 942056-54-4 C₂₁H₁₉F₁₇O₂ 
• 1071528-13-6 (-)-(E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl 3,3-difluoro-2-(((1R)-1-phenyl-2-methoxyethyl)imino)-5-hexenoate 
• 925671-39-2 2,6-dimethoxy-4-[3-(perfluorooctyl)propyloxy]benzaldehyde 
• 1250397-40-0 (E)-methyl 3-(4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)phenyl)acrylate 
• 1616628-13-7 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl (4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside)uronate 

Relevant academic research and scientific papers

Syntheses of fluorous quaternary ammonium salts and their application as phase transfer catalysts for halide substitution reactions in extremely nonpolar fluorous solvents

Perfluoromethyldecalin solutions of the fluorous alkyl halides Rf8(CH2)mX (m=2, 3; X=Cl, I) are inert toward aqueous NaCl, KI, KCN, and NaOAc. However, substitution occurs at 100 °C in the presence of 10 mol % of the fluorous ammonium salts (Rf8(CH2)2)(Rf8(CH2)5)3N+ I- (1) or (Rf8(CH2)3)4N+ Br- (2) (10 mol %), which are fully or partially soluble in perfluoromethyldecalin under these conditions. Stoichiometric reactions of (a) 1 and Rf8(CH2)3Br, and (b) 2 and Rf8(CH2)2I are conducted in perfluoromethyldecalin at 100 °C, and yield the same Rf8(CH2)mI/Rf8(CH2)mBr equilibrium ratio (60-65:40-35). This shows that ionic displacements can take place in extremely nonpolar fluorous phases, and suggests a classical phase transfer mechanism for the catalyzed reactions. Interestingly, the non-fluorous ammonium salt mixture CH3(CH3(CH2)m)3N+ Cl- (3, Aliquat 336; m=2:1 7/9) also catalyzes halide substitutions, but under triphasic conditions with 3 suspended between the lower fluorous and upper aqueous layers. NMR experiments establish very low solubilities in both phases, suggesting interfacial catalysis.

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.

Br?nsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water

One-pot three-component synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines in water was efficiently realized in the presence of the Br?nsted acidic imidazolium salts containing perfluoroalkyl tails in good yields. The method provided several advantages such as low catalyst loading; recycle of the catalyst and simple work procedure.

Ionic transformations in extremely nonpolar fluorous media: Phase transfer catalysis of halide substitution reactions

Fluorous solutions of alkyl halides R18(CH2) mX (m = 2, 3; X = Cl, Br, I) are inert toward solid or aqueous NaCl, NaBr, and Kl, but halide substitution occurs in the presence of fluorous phosphonium salts (10 mol %, 76-100 °C).

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.

Fluorous biphasic catalysis. 2. Synthesis of fluoroponytailed amine ligands along with fluoroponytailed carboxylate synthons, [M(C8F17(CH2)2CO2) 2] (M = Mn2+ or Co2+)

Fluorous biphasic catalysis (FBC) is a relatively new concept for homogeneous catalysis where the fluorocarbon soluble catalyst resides in a separate phase from the substrate and products. Therefore, separation of the catalyst and the products occurs by a

A convenient access to triarylphosphines with fluorous phase affinity

Perfluorocarbon-soluble triarylphosphines with electronic properties similar to those of tris(p-methoxyphenyl)phosphine can be easily prepared through O-alkylation of tris(p-hydroxyphenyl)phosphine oxide and subsequent reduction with trichlorosilane.

Fluorous Biphasic Catalysis: Complexation of 1,4,7-3-1,4,7-Triazacyclononane with (M = Mn, Co) To Provide Perfluoroheptane-Soluble Catalysts for Alkane and Alkene Functionalization in the Presence of t-BuOOH and O2

Keywords: biphasic catalysis; cobalt; fluorohydrocarbons; manganese; oxidations