Ethyl trifluoromethanesulfonate

Ethyl trifluoromethanesulfonate Basic information
Product Name:Ethyl trifluoromethanesulfonate
Synonyms:Ethyl trifluoromethylsulfonate;Ethyl trifluoromethanesulfonate,98%;Ethyl Triflate Trifluoromethanesulfonic Acid Ethyl Ester;Ethyltrifluormethansulfonat;Ethyl trifluoroMethanesulfonat;Ethyl trifluoromethanesulfote;ETHYL TRIFLATE;ETHYL TRIFLUOROMETHANESULFONATE
CAS:425-75-2
MF:C3H5F3O3S
MW:178.13
EINECS:207-037-3
Product Categories:Analytical/Chromatography;Derivatization Reagents;Alkyl Transfer;Acylation ReagentsDerivatization Reagents;Derivatization Reagents GC;Reagents for Acylation;C-X Bond Formation (Non-Halogen);Synthetic Reagents
Mol File:425-75-2.mol
Ethyl trifluoromethanesulfonate Structure
Ethyl trifluoromethanesulfonate Chemical Properties
Boiling point 115 °C (lit.)
density 1.374 g/mL at 25 °C (lit.)
refractive index n20/D 1.336(lit.)
Fp 96 °F
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform, Methanol (Slightly)
form Oil
color Colourless
Specific Gravity1.374
Water Solubility Hydrolyzes in water.
Sensitive Hygroscopic
BRN 1770746
Stability:Volatile
InChIKeyUVECLJDRPFNRRQ-UHFFFAOYSA-N
CAS DataBase Reference425-75-2(CAS DataBase Reference)
EPA Substance Registry SystemMethanesulfonic acid, trifluoro-, ethyl ester (425-75-2)
Safety Information
Hazard Codes C,T,F
Risk Statements 10-34
Safety Statements 16-26-36/37/39-45
RIDADR UN 2920 8/PG 2
WGK Germany 2
3
Hazard Note Highly Toxic
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29049090
MSDS Information
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Ethyl trifluoromethanesulfonate English
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Ethyl trifluoromethanesulfonate Usage And Synthesis
Chemical PropertiesClear colorless to yellow liquid
UsesEthyl trifluoromethanesulfonate is a powerful ethylating agent. due to the strong electron-absorbing ability of trifluoromethanesulfonyl, the reactivity is much higher than that of conventional alkylation reagents such as bichloride or alkyl sulfonate.
SynthesisTriethyl orthoformate (4.44g,30mmol) was slowly added to trifluoromethanesulfonic anhydride (8.47g,30mmol) under ice bath, transferred to 25°C for reaction, monitored by NMR for 15 min, and the reaction was completed, distilled under reduced pressure to obtain 10.15g of ethyl trifluoromethanesulfonate colorless liquid in 94% yield.
Purification MethodsThe ester reacts slowly with H2O and aqueous alkali. If its IR has no OH bands (~3000 cm-1) then purify it by redistillation. If OH bands are present, then dilute with dry Et2O and shake (carefully) with aqueous NaHCO3 until effervescence ceases, then wash with H2O and dry (MgSO4), filter, evaporate and distil the residue under a slight vacuum then at atmospheric pressure in a N2 atmosphere. IT IS A POWERFUL ALKYLATING AGENT, AND THE FUMES ARE VERY TOXIC — PERFORM ALL OPERATIONS IN AN EFFICIENT FUME CUPBOARD. [Gramstad & Haszeldine J Chem Soc 173 1956, Howells & McCown Chem Rev 77 69 1977, Beilstein 3 IV 34.]
SILVER TRIFLUOROMETHANESULFONATE Scandium trifluoromethanesulfonate Trifluoromethanesulfonic acid Methyl trifluoromethanesulfonate Ethyl 4,4,4-trifluoroacetoacetate Ethanol Ethyl formate Methanesulfonic acid TRIFLUOROMETHANESULFONYL CHLORIDE Ethyl methanesulfonate Ethylparaben Ethyl trifluoroacetate ISOXADIFEN-ETHYL Ethyl acetate Trifluoromethyl iodide Trifluoromethane Ethyl acrylate Ethyl cyanoacetate

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