Triethylsilyl trifluoromethanesulfonate

Base Information

• Chemical Name: Triethylsilyl trifluoromethanesulfonate
• CAS No.: 79271-56-0
• Molecular Formula: C7H15F3O3SSi
• Molecular Weight: 264.341
• Hs Code.: 29319090
• European Community (EC) Number: 279-124-4
• DSSTox Substance ID: DTXSID00229597
• Nikkaji Number: J267.450E
• Wikidata: Q72510683
• Mol file: 79271-56-0.mol

Synonyms:Triethylsilyl trifluoromethanesulfonate;79271-56-0;Triethylsilyl Triflate;Triethylsilyl trifluoromethanesulphonate;triethylsilyltrifluoromethanesulfonate;Trifluoromethanesulfonic Acid Triethylsilyl Ester;Methanesulfonic acid, trifluoro-, triethylsilyl ester;EINECS 279-124-4;MFCD00000407;TES triflate;1,1,1-triethylsilyl trifluoromethanesulfonate;Et3SiOTf;TESOTf;Triethylsilyltriflate;SCHEMBL36993;STMPXDBGVJZCEX-UHFFFAOYSA-;DTXSID00229597;AMY15603;CS-B0887;Triethylsilyl trifluromethanesulfonate;AKOS015856666;triethylsilyl trifluoromethane-sulfonate;TRIETHYLSILTRIFLUOROMETHANE-SULFONATE;triethylsilyl tris(fluoranyl)methanesulfonate;FT-0652499;T1689;Triethylsilyl Trifluoromethanesulfonate, 98%;Triethylsilyl trifluoromethanesulfonate, 99%;EN300-159832;S17625;Trifluoromethanesulfonic acid triethylsilylester;A839632;J-525086;InChI=1/C7H15F3O3SSi/c1-4-15(5-2,6-3)13-14(11,12)7(8,9)10/h4-6H2,1-3H3

Chemical Property of Triethylsilyl trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: clear colorless to light brown fuming liquid
• Vapor Pressure: 0.327mmHg at 25°C
• Refractive Index: n20/D 1.389(lit.)
• Boiling Point: 207.3 °C at 760 mmHg
• Flash Point: 79.2 °C
• PSA: 51.75000
• Density: 1.182 g/cm³
• LogP: 3.93860
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Triethylsilyl Trifluoromethanesulfonate is readily sol hydrocarbons, dialkyl ethers, halogenated solvents. CH2Cl2 is employed most commonly. Reactions in 1,2-dichloroethane proceed faster than those in CCl4 or Et2O. Protic solvents and THF react with trialkylsilyl triflates and are therefore not suitable.
• Water Solubility.: Miscible with dichloromethane, hydrocarbons, dialkyl ethers and halogenated solvents. Immiscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 264.04632653
• Heavy Atom Count: 15
• Complexity: 281

Purity/Quality:

99.9% ^*data from raw suppliers

Triethylsilyl trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,F
• Statements: 34-14
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F
• General Description: Triethylsilyl trifluoromethanesulfonate (TESOTf) is a highly effective catalyst for the reductive cleavage of triphenylmethyl (trityl) ethers when used with triethylsilane (Et3SiH). It enables mild and chemoselective deprotection of primary alcohols, even in the presence of acid-sensitive functional groups, making it particularly valuable in carbohydrate chemistry. The reaction proceeds via an equilibrium involving trityl ether, triethylsilyl ether, and trityl cation, ultimately reducing the trityl cation to triphenylmethane while regenerating the catalyst. TESOTf has demonstrated high efficiency in cleaving trityl ethers from diverse substrates, including sugar derivatives, with excellent yields under mild conditions. Additionally, it serves as a promoter in glycosylation reactions, such as in the synthesis of amphiphilic chitoheptaose derivatives, where it facilitates the formation of glycosidic bonds. Its versatility in organic synthesis underscores its utility as both a catalyst and a promoter in selective transformations.

Technology Process of Triethylsilyl trifluoromethanesulfonate

There total 5 articles about Triethylsilyl trifluoromethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

triethylsilyl chloride (994-30-9) + trifluorormethanesulfonic acid (1493-13-6) → triethylsilyl trifluoromethyl sulfonate (79271-56-0)

Guidance literature:

In n-heptane; for 14h; Heating;

DOI:10.1002/ijch.199900023

Reference yield:

triethylsilane (617-86-7) + Silantetrayltetrakis(trifluormethansulfonat) (66469-45-2) → triethylsilyl trifluoromethyl sulfonate (79271-56-0) + bis(trifluoromethanesulfonyloxy)silane (127808-37-1) + chlorotris(trifluoromethylsulfonyloxy)silane (127808-35-9)

Guidance literature:

In dichloromethane-d2; at 20 ℃; for 504h;

DOI:10.1002/anie.202103414

Reference yield:

triethylsilane (617-86-7) + trifluorormethanesulfonic acid (1493-13-6) → triethylsilyl trifluoromethyl sulfonate (79271-56-0)

Guidance literature:

In dichloromethane; at 0 ℃;

DOI:10.1021/jo702557d

upstream raw materials:

triethylsilyl chloride

trifluorormethanesulfonic acid

triethylsilane

Silantetrayltetrakis(trifluormethansulfonat)

Downstream raw materials:

8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate

Triethyl-((E)-1-methyl-4-phenyl-but-3-enyloxy)-silane

(5R,6S)-3-(3-Nitro-phenyl)-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

1-benzyl-3-(triethylsiloxy)azetidine

Refernces

Triethyl- (or trimethyl-)silyl triflate-catalyzed reductive cleavage of triphenylmethyl (trityl) ethers with triethylsilane

10.1021/ol0271988

The study presents a novel method for the reductive cleavage of triphenylmethyl (trityl) ethers using triethylsilane (Et3SiH) in the presence of a catalytic amount of triethylsilyl triflate (TESOTf) or trimethylsilyl triflate (TMSOTf). This method allows for the selective protection and subsequent cleavage of primary alcohols in the presence of acid-sensitive functional groups, which is particularly useful in carbohydrate chemistry. The reaction is mild, rapid, and highly chemoselective, with the cleavage process involving an equilibrium between trityl ether, triethylsilyl ether, and trityl cation, leading to the reduction of the trityl cation to triphenylmethane and regeneration of the silyl triflate catalyst. The study demonstrates the effectiveness of this method with a variety of 1,10-decanediol derivatives, sugar derivatives, and trehalose derivatives, showing high yields of the corresponding alcohols after mild acidic treatment. The chemicals used in the study include trityl ethers, triethylsilane, TESOTf, TMSOTf, and various protecting groups such as acetyl, pivaloyl, benzoyl, benzyl, MPM, and TBDPS, which served to protect the primary alcohols during the cleavage process.

Synthesis of amphiphilic chitoheptaose derivative

10.1016/S0040-4039(97)10104-6

The study focuses on the synthesis of an amphiphilic chitoheptaose derivative, tetradecyl-4-O-chitohexaosyl-2-deoxy-2-tetradecanamido-?-D-glucopyranoside hexahydrochloride, which is expected to enhance biological activities through clustering. The synthesis involves multiple steps, starting with the preparation of a heptasaccharide skeleton using a disaccharide synthon for chain elongation. Key chemicals include NJV-diacetylchitobiose, which is converted into a pentenyl glycoside and then benzylidenated to form an elongation synthon. The 1,6-anhydro precursor of the reducing end is glycosylated using N-iodosuccinimide (NIS) and triethylsilyltriflate (TESOTf) as promoters. The introduction of hydrophobic groups involves acylation with tetradecanoyl chloride and a subsequent one-pot synthesis of tetradecyl glycoside. The final product is obtained after deprotection and purification, resulting in a compound that forms micelles in water, as indicated by its solubility in a 3% aqueous solution.