83766-52-3

Usage

Uses

Used in the Synthesis of Organocatalysts:
4-(Heptadecafluorooctyl)aniline is used as a key intermediate in the synthesis of fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst. The incorporation of the heptadecafluoroocty group into the organocatalyst enhances its solubility in fluorous solvents, which is beneficial for applications in fluorous biphasic catalysis. This allows for efficient separation and recovery of the catalyst, as well as the potential for its reuse in multiple reaction cycles.
In the field of asymmetric catalysis, the use of bifunctional organocatalysts has gained significant interest due to their ability to promote a wide range of enantioselective transformations. The introduction of the 4-(heptadecafluorooctyl)aniline moiety into the organocatalyst structure can contribute to the overall performance of the catalyst, including its enantioselectivity, reactivity, and stability.
Furthermore, the unique properties of 4-(heptadecafluorooctyl)aniline may also find applications in other areas of chemistry, such as the development of new materials with specific surface properties, or as a component in the synthesis of pharmaceuticals or agrochemicals where fluorinated moieties can influence the lipophilicity, bioavailability, or metabolic stability of the final product.

InChI:InChI=1/C14H6F17N/c15-7(16,5-1-3-6(32)4-2-5)8(17,18)9(19,20)10(21,22)11(23,24)12(25,26)13(27,28)14(29,30)31/h1-4H,32H2

Upstream product

• 507-63-1 1-iodoheptadecafluorooctane 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 540-37-4 p-aminoiodobenzene 

Downstream Products

• 206560-77-2 1-bromo-4-(heptadecafluorooctyl)benzene 
• 120606-38-4 isothiocyanato-4-(n-perfluorooctyl)benzene 

Relevant academic research and scientific papers

Highly Site-Selective Formation of Perfluoroalkylated Anilids via a Protecting Strategy by Molybdenum Hexacarbonyl Catalyst

Introducing a perfluoroalkyl group on the aromatic ring with high site selectivity remains a challenging area in organofluorine chemistry. We herein report a highly para-selective C-H perfluoroalkylation of aniline substrates using the molybdenum hexacarbonyl catalyst. Various substituted anilids derived from anilids were well-tolerated, affording the corresponding products in moderate to good yields. Preliminary mechanism studies and density functional theory calculations revealed the coordination of Mo catalyst with amides as the key factor to realize para selectivity.

A fast response photo isomerous 4-Fluoalkyl azo-phenyl propylene ether and its preparation method

The invention discloses rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and a preparation method thereof. The general structural formula of 4-perfluoroalkyl azobenzene allyl ether is shown in the Specification. The preparation method includes the following steps: dissolving the starting compounds, 4-iodoaniline and fluorine-containing alkyl iodide, into a high boiling point solvent, and under the protection of nitrogen, heating, and catalyzing the solvent by copper powder to obtain fluoroalkyl aniline; after diazotizing fluoroalkyl aniline using hydrochloric acid/nitrite system at a temperature of 0-5 DEG C, enabling the diazotized solution to react with the phenol alkaline solution to obtain perfluoroalkyl azo phenol; under the protection of nitrogen, heating perfluoroalkyl azo phenol and 3-bromopropylene in an anhydrous and oxygen-free polar solvent under a weak base condition to obtain 4-fluoroalkyl azobenzene propenyl ether. The fluorine-containing azobenzene compound photoisomerization provided by the invention can response rapidly, has an active functional group propenyl, is capable of participating in addition reactions or polymerization reactions, and can be applied widely.

Synthesis and characterization of photoresponsive POSS-based polymers and their switchable water and oil wettability on cotton fabric

Fast photoresponsive polymers containing polyhedral oligomeric silsesquioxane (POSS) and fluorinated azobenzene groups were successfully prepared via radical polymerization and characterized by NMR, FTIR, XRD, GPC, TGA, etc. The photoresponsive properties of the polymers were investigated through ultraviolet-visible absorption spectra. The trans-cis photoisomerization of the polymers in solution conformed to a first-order reaction kinetics equation. Superhydrophobicity and high oleophobicity of the cotton fabric coated with the polymer was observed when the POSS mole ratio was 3.0%. More importantly, the surface wettability of both water and oil on the coated fabrics could be intelligently controlled by applying UV irradiation in a short time.

Facile fabrication of multifunctional perfluoroalkyl functionalized graphene hydrogel via a synchronous reduction and grafting strategy

Fluorine-containing groups represent very promising functionalities because fluorine not only changes the physico-chemical properties of the graphene surface, it may also alter its electronic and magnetic properties. Herein, we describe, for the first tim

Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible-Light Irradiation

In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl

Synthesis and catalytic activity of fluorous chiral primary amine-thioureas

Three enantiopure fluorous thioureas featuring a free -NH2 group were synthesized by direct addition of aromatic isothiocyanates bearing a single n-C8F17 substituent in the ortho, meta and para position, respectively, to e

Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions

The synthesis of a minimally fluorous (52% F) diaryl diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described.

Inhibition of stannane-mediated radical rearrangements by a recoverable, minimally fluorous selenol

(equation presented) The preparation of a minimally fluorous diaryl diselenide is described. It is demonstrated that this diselenide, reduced in situ to the corresponding selenol, may be used in conjunction with stannanes to prevent a number of radical rearrangements. A 1 M solution of this selenol used in admixture with Breslow's water-soluble stannane can be used to significantly inhibit a cyclopropylcarbinyl ring opening. The combination of the fluorous selenol and the polar stannane permits recovery of the selenol by continuous fluorous extraction and isolation of a stannane-free hydrocarbon product.

Syntheses of Azobenzene Derivatives Having Fluoroalkyl Chain and Their Monomolecular Film Formation at the Air/Water Interface

The compounds, 4-(nonafluorobutyl)aniline, 4-(tridecafluorohexyl)aniline, and 4-(heptadecafluorooctyl)aniline were prepared by the reaction of corresponding perfluoroalkyl iodide with 4-iodoaniline in the presence of copper bronze.Six azobenzene derivatives (4-(4-fluorophenylazo)phenol, F(C6H4)N=N(C6H4)OH (1) (C6H4=p-phenylene), 4-(trifluoromethylphenylazo)phenol, CF3(C6H4)N=N(C6H4)OH (2), 4-(4-heptafluoropropylphenylazo)phenol, C3F7(C6H4)N=N(C6H4)OH (3), 4-(4-nonafluorobutylphenylazo)phenol, C4F9(C6H4)N=N(C6H4)OH (4), 4-(4-tridecafluorohexylphenylazo)phenol, C6F13(C6H4)N=N(C6H4)OH (5), and 4-(4-heptadecafluorooctylphenylazo)phenol, C8F17(C6H4)N=N(C6H4)OH (6)) were prepared by the usual diazo coupling reactions using 4-(perfluoroalkyl)aniline and phenol.The monomolecular film formations of the azobenzene derivatives at the air/water interface were investigated by surface pressure measurements to be dependent on the fluoroalkyl chain length (n).The compounds 5 (n=6) and 6 (n=8) formed stable monomolecular films at the air/water interface.