144951-90-6

Basic information

• Product Name: 1,1,2,2-TETRAFLUORO-2-(1,1,2,2-TETRAFLUOROETHOXY)-ETHANESULFONAMIDE
• Synonyms: 1,1,2,2-TETRAFLUORO-2-(1,1,2,2-TETRAFLUOROETHOXY)-ETHANESULFONAMIDE
• CAS NO: 144951-90-6
• Molecular Formula: C₄H₃F₈NO₃S
• Molecular Weight: 297.12
• Mol File: 144951-90-6.mol

Chemical Properties

• Boiling Point: 236.068 °C at 760 mmHg
• Flash Point: 96.571 °C
• Appearance: /
• Density: 1.750
• Vapor Pressure: 0.048mmHg at 25°C
• Refractive Index: 1.341
• CAS DataBase Reference: 1,1,2,2-TETRAFLUORO-2-(1,1,2,2-TETRAFLUOROETHOXY)-ETHANESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,2-TETRAFLUORO-2-(1,1,2,2-TETRAFLUOROETHOXY)-ETHANESULFONAMIDE(144951-90-6)
• EPA Substance Registry System: 1,1,2,2-TETRAFLUORO-2-(1,1,2,2-TETRAFLUOROETHOXY)-ETHANESULFONAMIDE(144951-90-6)

Safety Data

• Hazardous Substances Data: 144951-90-6(Hazardous Substances Data)

Usage

Uses

Used in Lithium-ion Batteries:
TFEEA is utilized as an electrolyte additive in lithium-ion batteries for its ability to enhance the performance and safety of these energy storage devices. Its high conductivity and low viscosity contribute to improved battery efficiency and longevity.
Used in Fluorinated Polymers:
In the field of polymer chemistry, TFEEA serves as a valuable component in the synthesis of fluorinated polymers, where its unique properties contribute to the development of materials with superior thermal and chemical resistance.
Used in Surfactants:
TFEEA is employed in the formulation of surfactants, where its fluorinated nature provides unique properties such as low surface tension and resistance to various environmental conditions, making it suitable for specialized applications.
Used as a Solvent for Organic and Inorganic Materials:
TFEEA's versatility extends to its use as a solvent for both organic and inorganic materials, where its stability and low viscosity facilitate the dissolution and processing of a wide range of substances.

InChI:InChI=1/C4H3F8NO3S/c5-1(6)2(7,8)16-3(9,10)4(11,12)17(13,14)15/h1H,(H2,13,14,15)

Upstream product

• 563-79-1 2,3-Dimethyl-2-butene 
• 144951-88-2 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide 
• 110-82-7 cyclohexane 
• 110-86-1 pyridine 
• 91-22-5 quinoline 
• 108-99-6 3-Methylpyridine 
• 110-91-8 morpholine 
• 603-76-9 1-methylindole 
• 120-72-9 indole 
• 93-58-3 benzoic acid methyl ester 
• 99-99-0 1-methyl-4-nitrobenzene 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 98-95-3 nitrobenzene 

Downstream Products

• 1242695-23-3 C₁₈H₁₅F₈NO₃S 

Relevant articles and documents

A convenient synthetic method for N-perfluoroalkanesulfonyl sulfilimines and sulfoximides

Reaction of perfluoroalkanesulfonyl amides with dialkyl sulfides or sulfoxides in the presence of stoichiometric amounts of lead tetra-acetate gave N-perfluoroalkanesulfonyl sulfilimines or N-perfluoroalkanesulfonyl sulfoximides, respectively, in moderate to good yield. - Keywords: Synthesis; Perfluoroalkanesulfonyl amides; N-perfluoroalkanesulfonyl sulfilimine; Sulfoximide

Study on the reactions of fluoroalkanesulfonyl azides with indole derivatives

The reactions of fluoroalkanesulfonyl azides 1 with different indole derivatives have been studied in detail. Treatment of 1 with equimolar amount of 1,3-dimethylindole 3 in 1,4-dioxane at room temperature afforded 2-(1,3-dimethyl-1,3-dihydro-indolinylidene) fluoroalkanesulfonylimines 5 in moderate to good yields. However, under the same reaction conditions, in the case of 1 with 1,2-dimethylindole 4, the corresponding 2-fluoroalkanesulfonyl (1,2-dimethyl-1H-indol-3-yl)-amide 6 was obtained in moderate yields. In addition, the reactions of 1 and indole 7 gave different products under different conditions. Possible mechanisms of these reactions were proposed.

Unexpected formation of the novel fluorinated diazenes

Fluoroalkanesulfonyl azides reacted with morpholine giving unexpectedly N-fluoroalkanesulfonyl-N-morpholino diazenes, which were fully characterized by using spectral methods and X-ray diffraction analysis.

A mild hydrodehalogenation of fluoroalkyl halides

A mild hydrodehalogenation reaction of fluoroalkyl halides (RfCF2X, X = Br, I) has been developed under weakly basic conditions, giving the corresponding hydrogenolysis products with moderate to high yields.

Study on the reactions of fluoroalkanesulfonyl azides with pyridine and its derivatives

The thermal reactions of fluoroalkanesulfonyl azides R(f)SO2N3 1 with pyridine and its derivatives have been investigated in detail. In many cases, N-fluoroalkanesulfonyl pyridinium imides Y+-N'SO2R(f) (Y: pyridine, 3- picoline, 3,5-lutidine and quinoline) and the hydrogen abstraction products R(f)SO2NH2 were obtained. 2-Picoline and 4-picoline reacted with 1 to give R(f)SO2NH2 exclusively. Interestingly, in the reaction of azides 1c IC2F4OC2F4SO2N3 with 4-picoline or quinoline, the ω-iodine of the azide was substituted to form ArC2F4OC2F4SO2NH2.

Unexpected formation of N-fluoroalkaneacyl anilides from the reactions of fluoroalkanesulfonyl azides with nitrobenzene and its derivatives

The thermal reactions of fluoroalkanesulfonyl azides RfCF 2SO2N3 1 with nitrobenzene and its derivatives XC6H4NO2 (X=H, F, Cl, CF3) gave the unexpected N-fluoroalkanea

Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

The pKa values of a series of fluoroalkanesulfonylamides were measured by potentiometric titration. Different kinds of alkyl halides and tosylates were employed to investigate the nucleophilicity of fluoroalkanesulfonylamides. Fluoroalkanesulfonylamides with longer fluoroalkyl chain have weaker nucleophilicity.

Study the reactions of fluoroalkanesulfonyl azides with N-alkylindoles

The reactions of fluoroalkanesulfonyl azides RfSO 2N3 1 with N-alkylindoles 2 have been studied in detail. It was found that both solvent and the amount of the azides seriously affected the product distribution. 1 reacted

Synthesis and Reactions of Fluoroalkanesulfonyl Azides and N,N-Dichlorofluoroalkanessulfonamides

Thermolysis or photolysis of fluoroalkanesulfonyl azides RFSO2N3 afforded the corresponding nitrene intermediates RFSo2N which reacted readily with alkanes, alkenes, benzene, dimethyl sulfide, dimethyl sulfoxide, pyridine and triphenylphosphine to give insertion or addition products.Similar results were obtained by the reactions of N,N-dichlorofluoroalkanesulfonamides, RFSO2NCl2, with the same reagents in the presence of zinc powder.Treatment of RFSO2NCl2 with alkene in the absence of zinc powder gave only a 1:1 adduct via a free-radical intermediate RfSO2NCl.

Synthesis of fluoroalkanesulfonyl azides and their reactions as fluoroalkanesulfonyl nitrene precursors

Thermolysis or photolysis of the title compounds with cyclohexane, Me2C = CMe2, methyl sulfide and triphenyl phosphine gave the corresponding insertion or addition products via the perfluoroalkanesulfonyl nitrene intermediate.