754-91-6

Usage

Uses

Used in Polymer Industry:
Perfluorooctanesulfonamide is used as a surfactant in the polymer industry for its ability to improve the properties of polymers, such as enhancing their thermal stability, chemical resistance, and surface properties.
Used in Firefighting Applications:
Perfluorooctanesulfonamide is used as an aqueous film-forming foam (AFFF) to extinguish hydrocarbon-based fires. Its unique properties allow it to form a stable film on the surface of the fire, effectively smothering the flames and preventing re-ignition.

Safety Profile

A poison by ingestion.When heated to decomposition it emits toxic vapors of SOx, NOx, and Fí.

InChI:InChI=1/C8H2F17NO2S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H2,26,27,28)

Upstream product

• 307-35-7 perfluorooctyl sulfofluorure 
• 238091-00-4 perfluorooctane-1-sulfonyl azide 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 7664-41-7 ammonia 
• 34834-20-3 perfluoro-n-octylsulfonylisocyanate 
• 423-50-7 tridecafluorohexanesulfonyl fluoride 
• 7795-95-1 octane-1-sulfonyl chloride 

Downstream Products

• 40630-61-3 heptadecafluoro-N,N-bis(2-hydroxyethyl)octanesulfonamide 
• 76752-82-4 {(C₂H₅)3NH}⁽¹⁺⁾*C₈F₁₇SO₂NH^(1-)={(C₂H₅)3NH}NHSO₂C₈F₁₇ 

Relevant academic research and scientific papers

Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium

A facile and efficient synthesis of polyhydroquinoline derivatives was reported via four-component condensation reaction of aldehydes, dimedone, active methylene compounds, and ammonium acetate in the presence of Hf(NPf2)4 in C10F18 at 60 °C. The method offers several advantages including high yields, short reaction time, simple work-up procedure and catalyst reusability.

Ytterbium(III) bis(perfluorooctanesulfonyl)imide catalyzed one-pot synthesis of tetrahydrobenzo[b]pyrans in fluorous biphase system

Ytterbium(III) bis(perfluorooctanesulfonyl)imide [Yb(NPf2) 3] has been prepared, and used as an efficient catalyst for the synthesis of 4H-benzo[b]pyran derivatives by a one-pot three-component condensation of aldehydes, active methylene compounds, and dimedone in a fluorous biphase system (FBS). The reaction proceeds smoothly and affords the corresponding 4H-benzo[b]pyrans in moderate to excellent yields. The catalyst is selectively dissolved in the fluorous phase, can be recovered simply by phase separation and reused several times without any obvious decrease of activity.

Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and polyfluoroalkanesulfonamides 3 derivatives were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC50 values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules.

Sc[N(SO2C8F17)2]3 catalyzed condensation of β-naphthol and aldehydes in fluorous solvent: One-pot synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes

A facile synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes was proposed by one-pot condensation of β-naphthol with aryl or alkyl aldehydes by using Scandium bis(perfluorooctanesulfonyl)imide complex as catalyst and perfluorodecalin as sole solvent.

Three-component one-pot synthesis of pyrimidinone derivatives in fluorous media: Ytterbium bis(perfluorooctanesulfonyl)imide complex catalyzed biginelli-type reaction

(Chemical Equation Presented) The condensation of aromatic aldehyde, cyclopentanone, and urea or thiourea in the presence of Ytterbium bis(perfluorooctanesulfonyl)imide complex in perfluorodecalin was used to synthesize a variety of benzylidene heterobicyclic pyrimidinones in excellent yields.

Synthesis of symmetric and dissymetric bisperfluoroalkanesulfonylimides and evaluation of their inhibition on bovine carbonic anhydrase

This study describes a synthesis of symmetric and dissymmetric bis[(perfluoroalkane)-sulfonyl]imides by the reaction of the sodium salt of perfluoroalkanesulfonamide RFSO2NH-Na + (RF = C4F9, C6F 13, C8F17) with hexamethyldisilazane and perfluoroalkanesulfonylfluoride RFSO2F (RF - C4F9, C6F13, C8F 17). They are obtained, in two steps, in moderate overall yield. Moreover, this paper provides a study of their inhibition on bovine carbonic anhydrase.

Pharmaceutical Compositions Based on Fluorinated Sulphamides and Sulphinimides

Pharmacuetical composition comprising compounds of formula (I): [in-line-formulae]NZ1Z2Z3 ??(I) [/in-line-formulae] in which: Z1, Z2, Z3 each independently of the others represents: a hydrogen atom; C1-C6-alkyl group; a group —SO2R3 wherein R3 represents a linear or branched C1-C12-alkyl, -alkenyl or -alkynyl group, a C3-C10-cycloalkyl group or a C6-C10-aryl group, a (C1-C6)-alkyl-(C6-C14)-aryl group, or a C5-C10-heteroaryl group; it being understood that at least one of the groups Z1, Z2, Z3 represents a group of formula (II) [in-line-formulae]X—RF—(CH2)n—SO2—??(II) [/in-line-formulae] X, RF and n being as defined in claim 1.

Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel-Crafts acylation and Prins reaction in fluorous biphase system

In fluorous biphase system, hafnium(IV) bis(perfluorooctanesulfonyl)amide complex (Hf[N(SO2C8F17)2]4) was found to be a highly reactive and recyclable Lewis acid catalyst for Friedel-Crafts acylation and Prins reaction at significantly low catalyst loadings (≤1 mol%). In these reactions, Hf[N(SO2C8F17)2]4 is selectively soluble in the lower fluorous phase and can be recovered simply by phase separation. Furthermore, the catalyst can be reused without decrease of activity.

Synthesis and structure of environmentally relevant perfluorinated sulfonamides

Alkylated perfluorooctanesulfonamides are compounds of environmental concern. To make these compounds available for environmental and toxicological studies, a series of N-alkylated perfluorooctanesulfonamides and structurally related compounds were synthesized by reaction of the corresponding perfluoroalkanesulfonyl fluoride with a suitable primary or secondary amine. Perfluoroalkanesulfonamidoethanols were obtained from the N-alkyl perfluoroalkanesulfonamides either by direct alkylation with bromoethanol or alkylation with acetic acid 2-bromo-ethyl ester followed by hydrolysis of the acetate. N-Alkyl perfluorooctanesulfonamidoacetates were synthesized in an analogous way by alkylation of N-alkyl perfluoroalkanesulfonamides with a bromo acetic acid ester, followed by basic ester hydrolysis. Alternatively, N-alkyl perfluoroalkanesulfonamides can be alkylated with an appropriate alcohol using the Mitsunobu reaction. Perfluorooctanesulfonamide was synthesized from the perfluorooctanesulfonyl fluoride via the azide by reduction with Zn/HCl. All perfluorooctanesulfonamides contained linear as well as branched C8F17 isomers, typically in a 10:1 to 30:1 ratio. The crystal structures of N-ethyl and N,N-diethyl perfluorooctanesulfonamide show that the S-N bond has considerable double bond character. This double bond character results in a significant rotational barrier around the S-N bond (ΔG≠ = 62-71 kJ mol-1) and a preferred solid state and solution conformation in which the N-alkyl groups are oriented opposite to the perfluorooctyl group to minimize steric crowding around the S-N bond.

New synthesis of polyfluoroalkanesulfonylureas

This study describes a new synthesis of F-alkanesulfonyl ureas by reaction of the sodium salt of perfluoroalkane sulfonamide (RF = C4F9, C6F13) with some isocyanates in anhydrous THF. The perfluorinated sulfonylureas are obtained, in one step, from moderate to good yields.