33454-82-9

Basic information

• Product Name: Lithium triflate
• Synonyms: Methanesulfonicacid,trifluoro-,lithiumsalt;trifluoro-methanesulfonicacilithiumsalt;Lithium triflate, Trifluoromethanesulfonic acid lithium salt;Lithium trifluoromethanesulfonate ,97%;Lithium trifluoromethanesulfonate,Lithium triflate, Trifluoromethanesulfonic acid lithium salt;TrifluoroMethyl sulfonic acid lithiuM;LithiuM trifluoroMethanesulfonat;Methanesulfonic acid,1,1,1-trifluoro-, lithiuM salt (1:1)
• CAS NO: 33454-82-9
• Molecular Formula: CF₃O₃S*Li
• Molecular Weight: 156.01
• EINECS: 251-528-5
• Product Categories: metal triflate compounds;triflate;Organic-metal salt;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Li (Lithium) Compounds;Metal Triflates;Synthetic Organic Chemistry;Typical Metal Compounds
• Mol File: 33454-82-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 162 °C at 760 mmHg
• Appearance: White or colorless/Powder
• Density: 1,9 g/cm3
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Water
• Water Solubility: soluble
• Sensitive: Moisture Sensitive
• Stability: hygroscopic
• BRN: 4301818
• CAS DataBase Reference: Lithium triflate(CAS DataBase Reference)
• NIST Chemistry Reference: Lithium triflate(33454-82-9)
• EPA Substance Registry System: Lithium triflate(33454-82-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 33454-82-9(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Lithium trifluoromethanesulfonate is mixed with ceramic filler to prepare polyethylene oxide films in order to improve the electrochemical and mechanical characteristics of the membrane, which is used in the lithium batteries. It acts as a doping salt used in the preparation of nano manganese-composite polymer electrolytes.

General Description

This product has been enhanced for energy efficiency.

InChI:InChI=1/CHF3O3S.Li/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1

Synthetic route

trifluorormethanesulfonic acid (1493-13-6) + lithium chloride → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In water at 100℃; for 1h;	93.3%

LiSn(C6H5)2CH3 (4167-85-5) + {(CH3)3C}{(CH3)2CH}Si(OSO2CF3)2 (135580-50-6) + trifluorormethanesulfonic acid (1493-13-6) + dimethyl amine (124-40-3) → {(CH3)3C}{(CH3)2CH}{(CH3)2N}SiSn{N(CH3)2}(C6H5)CH3 (135580-44-8) + lithium trifluoromethanesulfonate (33454-82-9) + [Me2NH2]OTf (79430-76-5)

Conditions	Yield
In diethyl ether; toluene byproducts: C6H6; Ar-atmosphere; addn. of LiSnPh2Me to Si-derivative in ether (-&0°C), toluene addn., addn. of triflic acid (-70°C), stirring (3 h, -70°C), addn. of Me2NH (-40°C); sepn. of Me2NH2OSO2CF3, filtration, evapn. (vac.), fractional distn.; mixt. of stereoisomers (1 : 1) not sepd.; elem. anal.;	A 54% B n/a C n/a

barium trifluoromethanesulfonate (2794-60-7) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
With lithium sulfate In water for 24h;

bis(trifluoromethyl)sulfone (72971-96-1) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
With lithium hydroxide In methanol at 0℃; for 0.5h;

barium trifluoromethanesulfonate (2794-60-7) + lithium hydroxide (1310-65-2) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
With sulfuric acid In water
With dild. H2SO4 In water

trifluorormethanesulfonic acid (1493-13-6) + lithium hydroxide (1310-65-2) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
byproducts: H2O;

Trifluoromethanesulfonyl fluoride (335-05-7) + lithium hydroxide (1310-65-2) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
byproducts: HF;

Lithium enolate of the acetaldehyde (675825-21-5) + copper(II) bis(trifluoromethanesulfonate) (34946-82-2) → lithium trifluoromethanesulfonate (33454-82-9)

copper(II) bis(trifluoromethanesulfonate) (34946-82-2) + 1,2,2-triphenyl-ethanone; lithium enolate (27557-78-4) → lithium trifluoromethanesulfonate (33454-82-9)

(C6H5)2Sn(OSO2CF3)2 (27607-86-9) + lithium hexamethyldisilazane (4039-32-1) → (C6H5)2Sn{N(Si(CH3)3)2}(OSO2CF3) (135580-43-7) + lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In diethyl ether Ar-atmosphere; mixing at -50°C, warming to room temp. (during 2 h); evapn. (vac., room temp.), toluene addn. filtration off of Li-triflate, evapn. (vac.); elem. anal.;	A >95 B n/a

(C6H5)2Sn(OSO2CF3)2 (27607-86-9) + lithium phenylacetylide (4440-01-1) → (C6H5)2Sn(CCC6H5)OSO2CF3 (135580-42-6) + lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In diethyl ether Ar-atmosphere; mixing at -50°C, warming to room temp. (during 2 h); evapn. (vac., room temp.), toluene addn. filtration off of Li-triflate, evapn. (vac.); elem. anal.;	A >95 B n/a

bis(trifluoromethanesulfonyloxy)dimethylsilane (27607-78-9) + triphenylgermyl lithium (3839-32-5) → (CH3)2SiGe(C6H5)3(OSO2CF3) (135580-38-0) + lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In diethyl ether Ar-atmosphere; mixing at -70°C, stirring and warming to 0°C (3 h); evapn. (vac., 0°C), toluene addn., filtration off of Li-triflate (cooling), evapn. (vac.); elem. anal.;	A >95 B n/a

bis(trifluoromethanesulfonyloxy)dimethylsilane (27607-78-9) + lithium triphenylstannide (4167-90-2) → (CH3)2SiSn(C6H5)3(OSO2CF3) (135580-39-1) + lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In diethyl ether Ar-atmosphere; mixing at -70°C, stirring and warming to 0°C (3 h); evapn. (vac., 0°C), toluene addn., filtration off of Li-triflate (cooling), evapn. (vac.); elem. anal.;	A >95 B n/a

(C6H5)2Sn(OSO2CF3)2 (27607-86-9) + lithium diphenylphosphide (65567-06-8, 4541-02-0) → (C6H5)2Sn{P(C6H5)2}(OSO2CF3) (135604-57-8) + lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
In diethyl ether Ar-atmosphere; mixing at -50°C, warming to room temp. (during 2 h); evapn. (vac., room temp.), toluene addn. filtration off of Li-triflate, evapn. (vac.); elem. anal.;	A >95 B n/a

Trifluoromethanesulfonyl fluoride (335-05-7) → lithium trifluoromethanesulfonate (33454-82-9)

Conditions	Yield
With calcium oxide; lithium hydroxide In water for 9.5h;	1001 g

(4'-formyl-1,1'-biphenyl-4-yl)(triphenyl)phosphonium bromide + lithium trifluoromethanesulfonate (33454-82-9) → (4'-formyl-1,1'-biphenyl-4-yl)(triphenyl)phosphonium trifluoromethanesulfonate (1017241-87-0)

Conditions	Yield
In dichloromethane; water; acetonitrile for 1h;	100%

bis(4-fluorophenyl)sulfoxide (395-25-5) + lithium trifluoromethanesulfonate (33454-82-9) + 10H-acridin-9-one (578-95-0) → CF3O3S(1-)*C25H16F2NOS(1+) (1306757-09-4)

Conditions	Yield
Stage #1: bis(4-fluorophenyl)sulfoxide; 10H-acridin-9-one With methanesulfonic acid; phosphorus pentoxide In chlorobenzene at 50℃; for 2h; Inert atmosphere; Stage #2: lithium trifluoromethanesulfonate In dichloromethane for 1h;	100%

lithium trifluoromethanesulfonate (33454-82-9) + 2-[(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)methyl]-4,6-di-tert-butylphenol → C26H43F3LiNO8S (1572037-31-0)

Conditions	Yield
In diethyl ether at 20℃; Inert atmosphere; Schlenk technique;	100%

Tetraethylene glycol dimethyl ether (143-24-8) + lithium trifluoromethanesulfonate (33454-82-9) → Li(1+)*C10H22LiO5(1+)*CF3O3S(1-)

Conditions	Yield
at 79.84℃; for 0.5h;	100%

lithium trifluoromethanesulfonate (33454-82-9) + 1-benzyl-4-aza-1,4-diazoniabicyclo[2.2.2]octane triflate → 1-benzyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditriflate

Conditions	Yield
With fluorine In acetonitrile at -10 - 20℃; Inert atmosphere;	99%

1,2,3,4,5,6,7,8-octahydro-1,4;5,8-anti-dimethanoanthracene-9-iodonium(phenyl) tosylate + lithium trifluoromethanesulfonate (33454-82-9) → 1,2,3,4,5,6,7,8-octahydro-1,4;5,8-anti-dimethanoanthracene-9-iodonium(phenyl) triflate

Conditions	Yield
In chloroform at 20℃; for 0.5h;	99%

lithium trifluoromethanesulfonate (33454-82-9) + glycine (56-40-6) → Li(glycine)(CF3SO3)

Conditions	Yield
In ethanol at 80℃; for 0.333333h; Irradiation;	99%

C19H32N6O4(2+)*2Br(1-) + lithium trifluoromethanesulfonate (33454-82-9) → C19H32N6O4(2+)*2CF3O3S(1-)

Conditions	Yield
In water at 20℃; for 2h;	99%

C14H20NO4(1+)*I(1-) + lithium trifluoromethanesulfonate (33454-82-9) → N-[(methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside)-5-yl]pyridinium triflate

Conditions	Yield
In water at 20℃; for 24h;	99%

1,1-(1,4-phenylenedimethylene)bis(3-methyl-1H-imidazolium-1-yl) dibromide + lithium trifluoromethanesulfonate (33454-82-9) → 1-(2-hydroxyethyl)-3-methylimidazolium trifluoromethanesulfonate

Conditions	Yield
In ethanol; water at 20℃; for 4h;	98.6%

1-(1-methyl-1-pyrrolidinio)propane-3-sulfonate (876610-32-1) + lithium trifluoromethanesulfonate (33454-82-9) → triflate lithium 1-methylpyrrolidinium-1-propanesulfonate

Conditions	Yield
In methanol for 12h;	98%

tri-n-butyl(4-vinylbenzyl)phosphonium chloride + lithium trifluoromethanesulfonate (33454-82-9) → tributyl-(4-vinylbenzyl)phosphonium triflate

Conditions	Yield
In dichloromethane for 8h; Inert atmosphere;	98%
In dichloromethane	92%

[Os(NH3)5(2,3-η2-4-methoxystyrene)] bis(trifluoromethanesulfonate) + lithium trifluoromethanesulfonate (33454-82-9) + acrolein (107-02-8) → [Os(NH3)5(3,4-η2-8-formyl-2-methoxy-6,7,8,8a-tetrahydronaphthalene)] bis(trifluoromethanesulfonate)

Conditions	Yield
In acetonitrile N2; org. compd. dissoln. in CH3CN containing Li-salt, this soln. addn. to Os-compd., soln. stirring for ca. 12 h, pptn. on adding to stirring Et2O; ppt. filtration off, rinsing (ether), vac. drying; elem. anal.;	97%

di(rhodium)tetracarbonyl dichloride + C43H37N3P2 + lithium trifluoromethanesulfonate (33454-82-9) → C43H36ClLiN4OP2Rh(1+)*CF3O3S(1-)

Conditions	Yield
In dichloromethane for 0.166667h; Glovebox; Inert atmosphere;	97%

1,1'-(pyridine-2,6-diylbis(methylene))bis(3-(2-(adamantan-1-yl)ethyl)-1H-benzo[d]imidazol-3-ium) dibromide + lithium trifluoromethanesulfonate (33454-82-9) → 1,1'-(pyridine-2,6-diylbis(methylene))bis(3-(2-(adamantan-1-yl)ethyl)-1H-benzo[d]imidazol-3-ium) bis(trifluoromethane)sulfonate

Conditions	Yield
In methanol at 20℃; for 12h;	97%

lithium trifluoromethanesulfonate (33454-82-9) → trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
With sulfuric acid	96.8%

methyl (4-pyridyl) ketone (1122-54-9) + lithium trifluoromethanesulfonate (33454-82-9) → N-Fluoro-4-acetylpyridinium triflate (135182-95-5)

Conditions	Yield
With fluorine In acetonitrile at -40℃; for 3h;	96%

lithium trifluoromethanesulfonate (33454-82-9) + 1-butyl-3-methylimidazolium chloride (79917-90-1) → 1-(n-butyl)-3-methylimidazolium triflate (174899-66-2)

Conditions	Yield
In water	96%
In dichloromethane at 20℃; for 72h; Inert atmosphere;	86.7%
In acetonitrile Heating;	82.8%

4-(1-methylpyrrolidinium-1-yl)butane-1-sulfonate (872006-83-2) + lithium trifluoromethanesulfonate (33454-82-9) → triflate lithium 1-methylpyrrolidinium-1-butanesulfonate

Conditions	Yield
In methanol for 12h;	96%

4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride (42790-42-1) + lithium trifluoromethanesulfonate (33454-82-9) → 1-benzyl-4-aza-1,4-diazoniabicyclo[2.2.2]octane triflate

Conditions	Yield
In acetonitrile at 20℃; for 24h; Inert atmosphere;	96%

1,1'-(pyridine-2,6-diyl)bis(3-(4-(phenylethynyl)benzyl)-1H-benzo[d]imidazol-3-ium) dibromide + lithium trifluoromethanesulfonate (33454-82-9) → 1,1'-(pyridine-2,6-diyl)bis(3-(4-(phenylethynyl)benzyl)-1H-benzo[d]imidazol-3-ium) bis(trifluoromethane)sulfonate

Conditions	Yield
Stage #1: 1,1'-(pyridine-2,6-diyl)bis(3-(4-(phenylethynyl)benzyl)-1H-benzo[d]imidazol-3-ium) dibromide; lithium trifluoromethanesulfonate In methanol; acetonitrile at 85℃; for 12h; Stage #2: In water at 100℃; for 12h;	96%

Br(1-)*C23H39N2(1+) (1243209-98-4) + lithium trifluoromethanesulfonate (33454-82-9) → CF3O3S(1-)*C23H39N2(1+) (1243210-02-7)

Conditions	Yield
In water for 1h;	95%

C79H111N5O4(2+)*2Br(1-) + lithium trifluoromethanesulfonate (33454-82-9) → C79H111N5O4(2+)*2CF3O3S(1-)

Conditions	Yield
In methanol at 20℃; for 12h;	95%

1,1’-(pyridine-2,6-diylbis(methylene))bis(3-octyl-1H-benzimidazol-3-ium) dibromide + lithium trifluoromethanesulfonate (33454-82-9) → 1,1'-(pyridine-2,6-diylbis(methylene))bis(3-octyl-1H-benzimidazol-3-ium) bis(trifluoromethane)sulfonate

Conditions	Yield
In methanol at 20℃; for 12h;	95%

C26H40N4(2+)*2Br(1-) + lithium trifluoromethanesulfonate (33454-82-9) → C26H40N4(2+)*2CF3O3S(1-)

Conditions	Yield
In acetonitrile at 50 - 60℃; for 5h;	95%

pyridine-4-carbonitrile (100-48-1) + lithium trifluoromethanesulfonate (33454-82-9) → N-Fluoro-4-cyanopyridinium triflate (135182-97-7)

Conditions	Yield
With fluorine In acetonitrile at -40℃; for 3h;	94%

((2,6-bis(1-methylbenzimidazole-2-yl)pyridine)(Cl)Ru)2Cl2 (1210397-31-1, 1268524-46-4) + lithium trifluoromethanesulfonate (33454-82-9) + acetylacetone (123-54-6) → C26H26N5O3Ru(1+)*CF3O3S(1-)

Conditions	Yield
Stage #1: ((2,6-bis(1-methylbenzimidazole-2-yl)pyridine)(Cl)Ru)2Cl2 With trifluorormethanesulfonic acid for 1h; Stage #2: acetylacetone With triethylamine In methanol for 3h; Inert atmosphere; Reflux; Stage #3: lithium trifluoromethanesulfonate In water	94%

C22H30N6O4(2+)*2Br(1-) + lithium trifluoromethanesulfonate (33454-82-9) → C22H30N6O4(2+)*2CF3O3S(1-)

Conditions	Yield
In water at 20℃; for 2h;	94%

C19H34N4(2+)*2Br(1-) + C14H13ClN2Pt + lithium trifluoromethanesulfonate (33454-82-9) → C31H42N5Pt(1+)*CF3O3S(1-)

Conditions	Yield
Stage #1: C19H34N4(2+)*2Br(1-); C14H13ClN2Pt With triethylamine In acetonitrile at 90℃; for 24h; Stage #2: lithium trifluoromethanesulfonate In acetonitrile at 20℃;	94%

lithium trifluoromethanesulfonate (33454-82-9) + n-decyl-tri-n-butylphosphonium bromide (99045-50-8) → tributyldecylphosphonium trifluoromethanesulfonate

Conditions	Yield
In water; acetone at 20℃; for 15h;	93.4%

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 27607-86-9 (C₆H₅)2Sn(OSO₂CF₃)2 
• 4039-32-1 lithium hexamethyldisilazane 
• 34946-82-2 copper(II) bis(trifluoromethanesulfonate) 
• 27557-78-4 1,2,2-triphenyl-ethanone; lithium enolate 
• 675825-21-5 Lithium enolate of the acetaldehyde 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 1310-65-2 lithium hydroxide 
• 2794-60-7 barium trifluoromethanesulfonate 
• 72971-96-1 bis(trifluoromethyl)sulfone 
• 4440-01-1 lithium phenylacetylide 
• 65567-06-8 lithium diphenylphosphide 
• 27607-78-9 bis(trifluoromethanesulfonyloxy)dimethylsilane 
• 4167-90-2 lithium triphenylstannide 

Downstream Products

• 107264-00-6 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate 
• 116864-83-6 triphenyl(pyridin-2-yl)phosphonium trifluoromethanesulfonate 
• 1269141-77-6 (1R,4R,5R,6R)-6-benzyl-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octan-6-ium trifluoromethanesulfonate 
• 1493-13-6 trifluorormethanesulfonic acid 
• 923561-49-3 [((3,5-t-Bu₂C₆H₃)N=C(Me)C(Me)=N(3,5-t-Bu₂C₆H₃))Pt(triflato)2] 
• 675581-38-1 [FeH(2,2'-bipyridine)(PPh(OEt)2)3]CF₃SO₃ 
• 675581-39-2 [FeH(2,2'-bipyridine)(PPh₂(OEt))3]CF₃SO₃ 
• 193023-83-5 (Ru(2,2'-bipyridine)2(CO)2)⁽²⁺⁾ 
• 554-13-2 lithium carbonate 
• 58092-22-1 Co₄(CO)₁₀(μ₄-PPh)₂ 
• 1017241-87-0 (4'-formyl-1,1'-biphenyl-4-yl)(triphenyl)phosphonium trifluoromethanesulfonate 

Relevant articles and documents

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Preparation method of trifluoromethane sulfonic acid

The invention relates to a preparation method of trifluoromethane sulfonic acid. According to the preparation method, trifluoromethanesulphonyl fluoride and alkali metal hydroxide are subjected to a neutralizing hydrolysis reaction under existence of a fluorine fixing agent, after the reaction is completed, reaction liquid is filtered and dried, and fluorinated methyl sulfonic acid alkali metal salt is obtained; the fluorinated methyl sulfonic acid alkali metal salt and fuming sulphuric acid are subjected to acidizing treatment, then rectification is conducted multiple times, and high-purity trifluoromethane sulfonic acid is obtained. Through improvement of the preparation method, operating flexibility, production efficiency and product stability are improved, the comprehensive yield is raised, product purity can reach 99.90% or above, and the preparation method is suitable for industrial production.

Perfluoroalkylsulfone reactions with nucleophiles

Perfluorodialkylsulfones were found to react readily with metal hydroxides in water or alcohol solution and with ammonia to form fluorinated sulfonic acid derivatives.

Studies on trifluoromethanesulfonic acid. Part 2. Conductivities of solutions of metal trifluoromethanesulfonates and other bases in trifluoromethanesulfonic acid

Electrical conductivity measurements are reported for solutions in trifluoromethanesulfonic acid of a number of simple and complex bases, including univalent and divalent metal trifluoromethanesulfonates.The univalent metal salts, water, aniline, and acetic acid behave as fully dissociated bases, while the alkaline earth metal salts show considerable ion association.The trifluoromethanesulfonate anion appears to have an abnormally high mobility, as compared to the metal cations, and is believed to conduct by a proton-transfer mechanism.Dissociation constants for some weak organic bases and association constants for strontium and barium trifluoromethanesulfonates are estimated.Sulfuric acid behaves as a weak electrolyte, while sulfur trioxide is effectively a non-electrolyte.The conductivities of potassium nitrate and potassium dihydrogenphosphate are consistent with the formation of the nitryl cation and the phocphate acidium ion, respectively.