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Trimethylsilyl trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate structure
CAS No.
27607-77-8
Chemical Name:
Trimethylsilyl trifluoromethanesulfonate
Synonyms
TMSOTF;CT3795;27607-77-8;TMS TRIFLATE;TRIMETHYLSILY;TMSOTF, Fandachem;SILANE TMS-TRIFLATE;27607-77-8, Fandachem;TRIMETHYLSILYL TRIFLATE;Trifluormethansulfonicanhydrid
CBNumber:
CB2358138
Molecular Formula:
C4H9F3O3SSi
Formula Weight:
222.26
MOL File:
27607-77-8.mol

Trimethylsilyl trifluoromethanesulfonate Properties

Melting point:
25°C
Boiling point:
77 °C/80 mmHg (lit.)
Density 
1.228 g/mL at 25 °C (lit.)
vapor pressure 
4.7 hPa (20 °C)
refractive index 
n20/D 1.36(lit.)
Flash point:
78 °F
storage temp. 
Store below +30°C.
solubility 
sol aliphatic and aromatic hydrocarbons, haloalkanes, ethers.
form 
Fuming Liquid
Specific Gravity
1.15
color 
Clear colorless to light brown
Water Solubility 
REACTS
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
Merck 
14,9719
BRN 
1868911
InChIKey
FTVLMFQEYACZNP-UHFFFAOYSA-N
CAS DataBase Reference
27607-77-8(CAS DataBase Reference)
FDA UNII
Z84V0CBH9J
NIST Chemistry Reference
Trimethylsilyl trifluoromethanesulfonate(27607-77-8)
EPA Substance Registry System
Methanesulfonic acid, trifluoro-, trimethylsilyl ester (27607-77-8)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS05
Signal word  Danger
Hazard statements  H226-H314-H318
Precautionary statements  P260h-P405-P501a-P210-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P403+P235-P310
Hazard Codes  C,F
Risk Statements  10-14-34
Safety Statements  16-26-36/37/39-45-8
RIDADR  UN 2920 8/PG 2
WGK Germany  3
10-21
Autoignition Temperature 405 °C DIN 51794
Hazard Note  Corrosive/Flammable
TSCA  Yes
HazardClass  3
PackingGroup  III
HS Code  29310095

Trimethylsilyl trifluoromethanesulfonate price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 225649 Trimethylsilyl trifluoromethanesulfonate 99% 27607-77-8 10g $39.3 2021-03-22 Buy
Sigma-Aldrich 225649 Trimethylsilyl trifluoromethanesulfonate 99% 27607-77-8 50g $141 2021-03-22 Buy
TCI Chemical T0871 Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] >98.0%(T) 27607-77-8 5g $22 2021-03-22 Buy
TCI Chemical T0871 Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] >98.0%(T) 27607-77-8 25g $67 2021-03-22 Buy
Alfa Aesar A12535 Trimethylsilyl trifluoromethanesulfonate 99% 27607-77-8 10g $36.6 2021-03-22 Buy

Trimethylsilyl trifluoromethanesulfonate Chemical Properties,Uses,Production

Chemical Properties

clear colourless to light brown fuming liquid

Physical properties

bp 45–47 °C/17 mmHg, 39–40 °C/12 mmHg; d 1.225 g cm?3.

Uses

Trimethylsilyl Trifluoromethanesulfonate is generally used following reactions:1. Silylation. TMSOTf is widely used in the conversion of carbonyl compounds to their enol ethers. The conversion is some 109 faster with TMSOTf/triethylamine than with chlorotrimethylsilane.


Dicarbonyl compounds are converted to the corresponding bisenol ethers; this method is an improvement over the previous twostep 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(trimethylsilyloxy)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
4.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 widespread employment. TMSOTf activates many selective glycosidation reactions.
5.O-Silylation. The formation of TMS ethers can be achieved by reacting the requisite alcohol with TMSOTf and an amine (triethylamine, pyridine, or 2,6-lutidine) in dichloromethane;C-Silylation. Depending on the reaction conditions, secondary 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 carbonyl group, the acetal unit, the nitrone moiety,…) thus facilitating different kinds of reactions;Acetal Activation. TMSOTf acts as a catalyst for the addition 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 reactions of epoxides take place in excellent yields;Cleavage of Protecting Groups. THP ethers of primary, secondary, and phenolic alcohols can be conveniently deprotected at room temperature; Hypervalent Iodine Chemistry. The formation of hypervalent iodine complexes is often promoted by TMSOTf.

Uses

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.

Uses

Catalyst and silylating agent for organic syntheses.

Trimethylsilyl trifluoromethanesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products


Trimethylsilyl trifluoromethanesulfonate Suppliers

Global( 437)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21032 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Shanghai Time Chemicals CO., Ltd.
+8618017249410 +86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
Fluoropharm Co., Ltd.
+8613336034509
+86 0571-85586753 sales@fluoropharm.com China 982 60
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26734 60
Zjartschem
+86-571-8723 8903 jocelynpan@zjarts.com
+86-571-87063838 jocelynpan@zjarts.com CHINA 997 58
Tianjin Zhongxin Chemtech Co., Ltd.
022-66880623
022-66880086 sales@tjzxchem.com CHINA 537 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29961 58

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View Lastest Price from Trimethylsilyl trifluoromethanesulfonate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-26 Trimethylsilyl Trifluoromethanesulfonate
27607-77-8
US $9.00 / KG 1KG 99% 10 ton Hebei Crovell Biotech Co Ltd
2021-07-22 Trimethylsilyl trifluoromethanesulfonate
27607-77-8
US $8.40 / KG 1KG 99% 50 tons Baoji Guokang Bio-Technology Co., Ltd.
2021-07-13 Trimethylsilyl trifluoromethanesulfonate
27607-77-8
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

Trimethylsilyl trifluoromethanesulfonate Spectrum


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