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
• Physical properties: 85–86 °C/12 mmHg; d 1.169 g cm?3.
• Uses: Triethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally more stable towards hydrolysis than are trimethylsilyl ethers, and consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product (eq 8). Triethylsilyl trifluoromethanesulfonate acts as a silylating agent. It is also useful as a Lewis acid catalyst. Further, it reacts with 1-diazo-3,3-dimethyl-butan-2-one to prepare 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone.

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:

(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

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

(1S,2R,3R)-1-methyl-3-(1-methyl-1-triethylsiloxyethyl)-2-(2'-nitrophenylselanylmethyl)cyclopentane

4-<(6-deoxy-3-O-methyl-2,4-O,O-bis(triethylsilyl)-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzonitrile

Refernces

• 1、 Driess, Matthias,Hermannsdorfer, André. "Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid". supporting information. p. 13656 - 13660. Retrieved 2021/05/03.
• 2、 -. "Process for producing novel naphthyridine derivatives". . . Retrieved 2008/06/13.