29420-49-3

Basic information

• Product Name: Potassium nonafluoro-1-butanesulfonate
• Synonyms: 1-Butanesulfonicacid,1,1,2,2,3,3,4,4,4-nonafluoro-,potassiumsalt;potassiumperfluorobutanesulfonate;potassium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulphonate;potassium perfluorobutanesulphonate;Perfluorobutansulfonic acid potassium salt;Perfluorobutanesulphonic acid potassium salt;Potassium nonafluorobutanesulphonate 98%;Potassiumnonafluorobutanesulphonate98%
• CAS NO: 29420-49-3
• Molecular Formula: C₄F₉O₃S*K
• Molecular Weight: 338.19
• EINECS: 249-616-3
• Product Categories: Organics
• Mol File: 29420-49-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: >400°C
• Appearance: /
• Density: 0.69
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Store below +30°C.
• Solubility: water: soluble100mg/mL, clear, colorless
• Stability: Very Hygroscopic
• BRN: 5200982
• CAS DataBase Reference: Potassium nonafluoro-1-butanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium nonafluoro-1-butanesulfonate(29420-49-3)
• EPA Substance Registry System: Potassium nonafluoro-1-butanesulfonate(29420-49-3)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 29420-49-3(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Uses

Potassium Perfluoro-1-butanesulfonate is standard for environmental testing and research. Also used on studies to compare the effect of glimepiride and nateglinde in all patients with type-2 diabetes.

Purification Methods

Wash it with H2O and dry it in vacuo. When the K salt is distilled with 100% H2SO4, it gives the free acid which can be distilled (b 105o/22mm, 210-212o/760mm) and then converted to the pure K salt. [Gramstad & Haszeldine J Chem Soc 2640 1957, Beilstein 2 IV 818.]

InChI:InChI=1/C4HF9O3S.K/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16;/h(H,14,15,16);

Synthetic route

Nonafluorobutanesulfonyl fluoride (375-72-4) → potassium nonaflate (29420-49-3)

Conditions	Yield
With potassium hydroxide; calcium oxide	96%
With KOH; CaO	96%

acetamide (60-35-5) + Nonafluorobutanesulfonyl fluoride (375-72-4) → potassium salt of octafluorobutane sulphonic acid + C6H3F9NO3S(1-)*K(1+) + potassium nonaflate (29420-49-3)

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 20℃;	A n/a B n/a C 75%

Nonafluorobutanesulfonyl fluoride (375-72-4) + potassium hydroxide → potassium nonaflate (29420-49-3)

Conditions	Yield
byproducts: HF;

perfluorobutanesulfonic acid (375-73-5) + potassium hydroxide → potassium nonaflate (29420-49-3)

Conditions	Yield
byproducts: H2O;

1,3-bis[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium chloride + potassium nonaflate (29420-49-3) → 1,3-bis[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium perfluorobutanesulfonate

Conditions	Yield
In methanol at 40℃; for 24h;	99.5%

potassium nonaflate (29420-49-3) → perfluorobutanesulfonic acid (375-73-5)

Conditions	Yield
With Amberlite IR-100 (H-form) ion exchange column In methanol	99%
In water passing over a cationic ion exchange resin;	>99
In water passing over a cationic ion exchange resin;	>99

potassium nonaflate (29420-49-3) + phenylboronic acid (98-80-6) → phenyl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate (25628-11-9)

Conditions	Yield
With C18H6BiF15O5S2; sodium phosphate; 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate In chloroform at 60℃; for 16h; Catalytic behavior; Reagent/catalyst; Molecular sieve; Inert atmosphere;	97%

potassium nonaflate (29420-49-3) + tetrakis(tert-butylamino)phosphonium chloride → tetrakis(tert-butylamino)phosphonium nonafluorobutanesulfonate

Conditions	Yield
In water	96%

4-(trimethylsilyl)phenyl trifluoromethanesulfonate (798553-21-6) + potassium nonaflate (29420-49-3) → 4-(trimethylsilyl)phenyl nonafluorobutane-1-sulfonate

Conditions	Yield
With C18H6BiF15O5S2; sodium phosphate; 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate In chloroform at 60℃; for 16h; Molecular sieve; Inert atmosphere;	96%

tetra-n-octylphosphonium bromide (23906-97-0) + potassium nonaflate (29420-49-3) → tetraoctylphosphonium nonafluorobutane-1-sulfonate

Conditions	Yield
In dichloromethane; water	96%

1-hexadecyl-3-(6-hydroxyhexyl)imidazolium chloride (1354971-75-7) + potassium nonaflate (29420-49-3) → C4F9O3S(1-)*C25H49N2O(1+) (1354971-80-4)

Conditions	Yield
In dichloromethane; water	95%

2-Methylphenylboronic acid (16419-60-6) + potassium nonaflate (29420-49-3) → o-tolyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (42096-33-3)

Conditions	Yield
With C18H6BiF15O5S2; sodium phosphate; 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate In chloroform at 60℃; for 16h; Molecular sieve; Inert atmosphere;	93%

1,3-didodecyl-2-undecylimidazolium bromide + potassium nonaflate (29420-49-3) → nonafluorobutanesulfonic acid-1,3-didodecyl-2-undecylimidazolium

Conditions	Yield
In ethanol; water for 1h; Reflux;	92.6%

1,3-dioctadecyl-2-heptadecylimidazolium bromide + potassium nonaflate (29420-49-3) → nonafluorobutanesulfonate 1,3-dioctadecyl-2-heptadecylimidazolium

Conditions	Yield
In ethanol; water for 1h; Reflux;	92.4%

formaldehyd (50-00-0) + Co(C3H8N2O2)(C2H8N2)2(3+)*3Cl(1-)*H2O = [Co(C3H8N2O2)(C2H8N2)2]Cl3*H2O + potassium nonaflate (29420-49-3) → Co(C5H12N2O2)(C2H8N2)2(3+)*3CF3(CF2)3SO3(1-) = [Co(C5H12N2O2)(C2H8N2)2](CF3(CF2)3SO3)3

Conditions

Yield

With HOAc/NaOAc; NaBH3CN In water addn. of aq. 37% HCHO to a stirred soln. of Co complex in HOAc/NaOAc/H2O, slow addn. of NaBH3CN in H2O, stirring (30 min), dilution with H2O; chromy. (elution with a gradient of 1-3 M HCl), concn. to dryness, redissoln. (H2O), slow add. of an almost boiling soln. of CF3(CF2)3SO3K in H2O, stirring (ice-cooling, 1 h), collection, washing (ice-water), drying(50°C); elem. anal.;

92%

potassium nonaflate (29420-49-3) + 1-octyl-3-methyl-imidazolium bromide → 1-methyl-3-octylimidazolium nonafluorobutanesulfonate

Conditions	Yield
In acetone at 20℃; for 48h;	92%

potassium nonaflate (29420-49-3) + 1-(2-ethoxy-2-oxoethyl)-1-methylpyrrolidinium chloride → 1-(2-ethoxy-2-oxoethyl)-1-methyl-pyrrolidinium nonafluorobutanesulfonate

Conditions	Yield
In dichloromethane at 20℃; for 48h;	92%

potassium nonaflate (29420-49-3) + 4-(2-phenylethynyl)phenyl trifluoromethanesulfonate (166663-45-2) → 4-(phenylethynyl)phenyl nonafluorobutane-1-sulfonate

Conditions	Yield
With C18H6BiF15O5S2; sodium phosphate; 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate In chloroform at 60℃; for 16h; Molecular sieve; Inert atmosphere;	92%

potassium nonaflate (29420-49-3) + 1-oxo-3,4-dihydro-1H-2-oxa-4a-azoniaanthracene bromide → 1-oxo-3,4-dihydro-1H-2-oxa-4a-azonia-anthracene; 1,1,2,2,3,3,4,4,4-nonafluoro-butane-1-sulfonate

Conditions	Yield
In ethanol for 12h; Heating;	91%

potassium nonaflate (29420-49-3) + 1-methyl-3-octylimidazol-3-ium chloride (64697-40-1) → 1-methyl-3-octylimidazolium nonafluorobutanesulfonate

Conditions	Yield
In acetonitrile	91%

[2,2]bipyridinyl (366-18-7) + ruthenium(III) chloride trihydrate + potassium nonaflate (29420-49-3) → [Ru(bpy)3][SO3C4F9]2

Conditions	Yield
Stage #1: [2,2]bipyridinyl; ruthenium(III) chloride trihydrate With ethylene glycol at 180℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: potassium nonaflate at 20℃; Schlenk technique; Inert atmosphere;	91%

1-n-butyl-4-methylpyridinium chloride (112400-86-9) + potassium nonaflate (29420-49-3) → 1-butyl-4-methylpyridinium nonafluorobutylsulfonate

Conditions	Yield
In acetonitrile	90%

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + potassium nonaflate (29420-49-3) + 4,4'-di-tert-butyl-2,2'-bipyridine (72914-19-3) → C40H40IrN4(1+)*C4F9O3S(1-)

Conditions	Yield
Stage #1: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2; 4,4'-di-tert-butyl-2,2'-bipyridine With ethylene glycol at 150℃; for 17h; Schlenk technique; Inert atmosphere; Stage #2: potassium nonaflate at 20℃; Schlenk technique; Inert atmosphere;	90%

C25H21S2(1+)*Br(1-) + potassium nonaflate (29420-49-3) → 4-(phenylthio)-3-methylphenyldiphenylsulfonium perfluorobutane sulfonate

Conditions	Yield
In dichloromethane at 20℃; for 1h;	90%

C25H21S2(1+)*Br(1-) + potassium nonaflate (29420-49-3) + acetyl chloride (75-36-5) → 4-(4-acetylphenylthio)-3-methylphenyldiphenylsulfonium perfluorobutane sulfonate

Conditions	Yield
Stage #1: C25H21S2(1+)*Br(1-); acetyl chloride With aluminum (III) chloride In dichloromethane at 10 - 20℃; for 2h; Stage #2: potassium nonaflate In dichloromethane at 20℃; for 1h;	90%

tetrabutyl phosphonium bromide (3115-68-2) + potassium nonaflate (29420-49-3) → tetrabutylphosphonium nonafluorobutane-1-sulfonate (220689-12-3)

Conditions	Yield
In ethanol; water at 20℃; for 0.25h; Product distribution / selectivity;	89.1%
In ethanol; water at 20℃; for 0.25h;	89.1%
In water at 20 - 80℃;	74%
In water at 20 - 85℃; for 0.25h; Product distribution / selectivity;	57.6%

potassium nonaflate (29420-49-3) + 1-butyl-2,3-dimethylimidazolium bromide → 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate

Conditions	Yield
In water at 20℃; for 12h;	88%

bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) (870987-64-7) + potassium nonaflate (29420-49-3) + 4,4'-di-tert-butyl-2,2'-bipyridine (72914-19-3) → C42H34F10IrN4(1+)*C4F9O3S(1-)

Conditions	Yield
Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 4,4'-di-tert-butyl-2,2'-bipyridine With ethylene glycol at 150℃; for 14h; Schlenk technique; Inert atmosphere; Stage #2: potassium nonaflate at 20℃; Schlenk technique; Inert atmosphere;	88%

C12H9F13N2S*HI + potassium nonaflate (29420-49-3) → 2-(1H,1H,2H,2H-perfluorooctylthio)-1-methylimidazolium perfluorobutanesulfonate

Conditions	Yield
In water at 20℃; for 24h;	87%

potassium nonaflate (29420-49-3) + 3-ethoxycarbonyl-2-phenylmethylisoquinolinium bromide → 3-ethoxycarbonyl-2-benzyl isoquinolinium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

Conditions	Yield
In ethanol for 12h; Heating;	86%

trimethylpropylammonium hepta(isooctyl)octasilsesquioxane iodide (1425925-31-0) + potassium nonaflate (29420-49-3) → trimethylpropylammonium tepta(isooctyl)octasilsesquioxane nonafluoro-1-butanesulfonate (1425925-34-3)

Conditions	Yield
In water at 50℃;	86%

C18H14FS(1+)*CF3O3S(1-) + potassium nonaflate (29420-49-3) → C18H14FS(1+)*C4F9O3S(1-)

Conditions	Yield
In dichloromethane; water at 25℃; for 4h;	86%

N,N-dimethyl-N-(n-heptyl)-N-[2-(methacryloyloxy)ethyl]ammonium bromide (107429-38-9) + potassium nonaflate (29420-49-3) → [2-(methacryloyloxy)ethyl]dimethylheptylammonium nonafluoro-1-butanesulfonate (1203998-93-9)

Conditions	Yield
In water at 20 - 60℃; Inert atmosphere;	85%

Upstream product

• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 375-73-5 perfluorobutanesulfonic acid 
• 60-35-5 acetamide 

Downstream Products

• 80543-67-5 (S)-2-Oxo-3-[(phenoxyacetyl)amino]-1-azetidinesulfonic acid, potassium salt 
• 137819-77-3 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-β-D-ribofuranosyl>cytosine 
• 220689-12-3 tetrabutylphosphonium nonafluorobutane-1-sulfonate 
• 108427-52-7 tetra-n-butylammonium nonafluoro-n-butanesulfonate 
• 42096-33-3 o-tolyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 25628-11-9 phenyl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate 

Relevant articles and documents

Synthesis and properties of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl)imides: A new subfamily of ionic liquids

A series of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl) imides was synthesized in high yields by quaternization of imidazole derivatives with various readily available alkylating reagents, followed by anion exchange with highly stable and non-hygroscopic potassium bis(nonafluorobutane-1- sulfonyl)imide. The latter was obtained by an improved method starting from ammonium chloride and nonafluorobutane-1-sulfonyl fluoride. The quaternary imidazolium salts thus obtained constitute a new subfamily of thermally stable and remarkably hydrophobic ionic liquids with melting points in the range 0-40°C and solubilities in water and organic solvents (aromatic hydrocarbons, dialkyl ethers) in the range of 0.5-1.5 wt%. The ionic liquids can be easily purified from ionic byproducts (e.g., halogenide salts) by aqueous extraction followed by thorough drying in a high vacuum without loss of yield. Due to the above features, these new ionic fluids may be considered as promising recyclable media in repeated catalytic processes.

Process for the preparation of bis-hydroxyphenyl-n-alkanes, new bis-hydroxyphenyl-n-alkanes and new alkanediones

Bis-hydroxyphenyl-n-alkanes are prepared by contacting dicarboxylic acids or dicarboxylic acid derivatives with fluorine-containing organic sulphonic acids, where appropriate with the addition of a phenolic compound, and converting the alkanediones, which are thus obtainable, into bis-hydroxyphenyl-n-alkanes by hydrogenation and, where appropriate, an additional ether cleavage. The invention also relates to new bis-hydroxyphenyl-n-alkanes and to new alkanediones.