Trimethylsilyl trifluoromethanesulfonate

Base Information

• Chemical Name: Trimethylsilyl trifluoromethanesulfonate
• CAS No.: 27607-77-8
• Deprecated CAS: 88188-06-1
• Molecular Formula: C4H9F3O3SSi
• Molecular Weight: 222.26
• Hs Code.: 29310095
• European Community (EC) Number: 248-565-4
• UNII: Z84V0CBH9J
• DSSTox Substance ID: DTXSID2067325
• Nikkaji Number: J208.993I
• Wikipedia: Trimethylsilyl_trifluoromethanesulfonate
• Wikidata: Q15427958
• Mol file: 27607-77-8.mol

Synonyms:Methanesulfonicacid, trifluoro-, trimethylsilyl ester (8CI,9CI);Silanol, trimethyl-, trifluoromethanesulfonate(8CI);Trifluoromethanesulfonic acid trimethylsilyl ester;Trimethylsilanoltrifluoromethanesulfonate;Trimethylsilyl triflate;Trimethylsilyl trifluoromethylsulfonate;Trimethylsilyl trifluoromethanesulfonate;

Chemical Property of Trimethylsilyl trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: clear colourless to light brown fuming liquid
• Vapor Pressure: 2.22E-09mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: n20/D 1.36(lit.)
• Boiling Point: 140 °C at 760 mmHg
• Flash Point: 38.5 °C
• PSA: 51.75000
• Density: 1.276 g/cm³
• LogP: 2.76830
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: sol aliphatic and aromatic hydrocarbons, haloalkanes, ethers.
• Water Solubility.: REACTS
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 221.99937634
• Heavy Atom Count: 12
• Complexity: 244

Purity/Quality:

99% min ^*data from raw suppliers

Trimethylsilyl trifluoromethanesulfonate 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F
• Hazard Codes: C,F
• Statements: 10-14-34
• Safety Statements: 16-26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• Physical properties: bp 45–47 °C/17 mmHg, 39–40 °C/12 mmHg; d 1.225 g cm?3.
• Uses: Trimethylsilyl Trifluoromethane?sulfonate is generally used following reactions:1. Silylation. TMSOTf is widely used in the conversion of car?bonyl compounds to their enol ethers. The conversion is some 109 faster with TMSOTf/triethylamine than with chlorotrimethy?lsilane.Dicarbonyl compounds are converted to the corresponding bis?enol ethers; this method is an improvement over the previous two?step method.In general, TMSOTf has a tendency toC-silylation which is seen most clearly in the reaction of esters, whereC-silylation dominates over O-silylation.2.Carbonyl Activation. 1,3-Dioxolanation of conjugated enals is facilitated by TMSOTf in the presence of 1,2-bis(trimethylsilyl?oxy)ethane. In particular, highly selective protection of sterically differentiated ketones is possible (eq 10).TMSOTf mediates a stereoselective aldol-type condensation of silyl enol ethers and acetals (or orthoesters). The nonbasic reaction conditions are extremely mild. The use of TMSOTf in aldol reactions of silyl enol ethers and ketene acetals with aldehydes is ubiquitous. Stereoselective cyclization of α,β-unsaturated enamide esters is induced by TMSOTf and has been used as a route to quinolizidines and indolizidines.3.The often difficult conjugate addition of alkynyl organometallic reagents to enones is greatly facilitated by TMSOTf. In particular, alkynyl zinc reagents (normally unreactive with α,β-unsaturated carbonyl compounds) add in good yield.The formation of nitrones by reaction of aldehydes and ketones with N-methyl-N,O-bis(trimethylsilyl)hydroxylamine is accelerated when TMSOTf is used as a catalyst; the acceleration is particularly pronounced when the carbonyl group is under a strong electronic influence.5. Methyl glucopyranosides and glycopyranosyl chlorides undergo allylation with allylsilanes under TMSOTf catalysis to give predominantly α-allylated carbohydrate analogs.Glycosidation is a reaction of massive importance and wide?spread employment. TMSOTf activates many selective glycosidation reactions.4.O-Silylation. The formation of TMS ethers can be achieved by reacting the requisite alcohol with TMSOTf and an amine (triethy?lamine, pyridine, or 2,6-lutidine) in dichloromethane;C-Silylation. Depending on the reaction conditions, sec?ondary amides can be either C-silylated or N-silylated;N-Silylation. The N-bis-silylation of α-amino acids with TMSOTf is only effective for glycine; for other α-amino acids N-mono-silylation prevails because the larger size of the carbon chain at the α-position hinders bis-silylation;C,O-Bis-silylation. Bis-silylation ofα,β-unsaturated carbonyl compounds can be achieved by palladium-TMSOTf-catalyzed addition of disilanes to enones, enals, or aromatic aldehydes via an η3-silyloxyallylpalladium intermediate;Carbonyl Activation. TMSOTf frequently acts as a Lewis acid and it is able to activate several functional groups (the car?bonyl group, the acetal unit, the nitrone moiety,…) thus facilitating different kinds of reactions;Acetal Activation. TMSOTf acts as a catalyst for the addi?tion of several nucleophiles (allylsilanes, allylstannanes, silyl enol ethers, trimethylsilyl cyanide) towardN,O-acetals;Nitrone Activation. The nucleophilic addition to aldonitrones depends on the nature of the metal involved and the presence/absence of an activator;Epoxide Ring Opening. One-pot alkylation-O-silylation re?actions of epoxides take place in excellent yields;Cleavage of Protecting Groups. THP ethers of primary, sec?ondary, and phenolic alcohols can be conveniently deprotected at room temperature; Hypervalent Iodine Chemistry. The formation of hyperva?lent iodine complexes is often promoted by TMSOTf. Trimethylsilyl Trifluoromethanesulfonate is a trialkylsilyl triflate used as a catalyst in organic synthesis. Trimethylsilyl Trifluoromethanesulfonate is used in combination with boron trifluoride eth yl ether to prepare a Lewis acid that is more powerful than its components and especially effective in acetonitrile solvent. Trimethylsilyl is a common reagent used in a Dieckmann-like cyclization of ester-imides and diesters. Catalyst and silylating agent for organic syntheses.

Technology Process of Trimethylsilyl trifluoromethanesulfonate

There total 45 articles about Trimethylsilyl 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: 98.0%

3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Guidance literature:

at 40 ℃; for 0.25h;

DOI:10.1055/s-1983-30430

Reference yield: 96.55%

chloro-trimethyl-silane (75-77-4) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Guidance literature:

In n-heptane; at 50 - 60 ℃; for 13h; Large scale;

Reference yield: 96.0%

trifluorormethanesulfonic acid (1493-13-6) + 1-(Trimethylsilyl)imidazole (18156-74-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Guidance literature:

In diethyl ether; at 10 ℃; for 1h;

upstream raw materials:

chloro-trimethyl-silane

silver trifluoromethanesulfonate

Hexamethyldisiloxane

trifluoromethylsulfonic anhydride

Downstream raw materials:

2,6-dimethyl-3,8-bis(trimethylsiloxy)octene

1-<2-<(trimethylsilyl)oxy>ethoxy>cyclohexene

trimetylsilylketene

1-<2-<(trimethylsilyl)oxy>ethoxy>-1-phenylethene

Refernces

• 1、 Schultheiss,Fluck. "". . p. 20,21-26. Retrieved 1978.
• 2、 Aizpurua, Jesus M.,Palomo, Claudio. "REAGENTS AND SYNTHETIC METHODS 55. NEW METHODS FOR THE PREPARATION OF t-BUTYLDIMETHYLSILYL TRIFLATE AND TRIMETHYLSILYL TRIFLATE.". . p. 6113 - 6114. Retrieved 1985.
• 3、 Johri, Kamalesh K.,Katsuhara, Yutaka,DesMarteau, Darryl D.. "Further reactions of chlorine(I) and bromine(I) trifluoromethanesulfonate and bromine(I)fluorosulfate". . p. 227 - 242. Retrieved 1982.
• 4、 -. "Synthesis method of trimethylsilyl trifluoromethanesulfonate". Paragraph 0018-0023. . Retrieved 2021/04/29.
• 5、 -. "A kind of triflic acid trimethyl Estersil method for the preparation of". Paragraph 0073-0076. . Retrieved 2017/04/11.