Trimethylsilyl trifluoromethanesulfonate structure

3D Mol Similar

Trimethylsilyl trifluoromethanesulfonate

: Iupac Name：trimethylsilyl trifluoromethanesulfonate; CAS No.: 27607-77-8; Molecular Weight：222.253; Modify Date.: 2022-11-02 12:48; Introduction:
Trimethylsilyl trifluoromethanesulfonate, with the chemical formula C4H9F3O3SSi and CAS registry number 27607-77-8, is a compound known for its applications in organic synthesis. This colorless liquid, also referred to as TMS triflate, is characterized by its trifluoromethanesulfonate and trimethylsilyl functional groups. It is commonly used as a strong acid catalyst and as a protecting group for alcohols and amines. TMS triflate is highly reactive and can be used in a variety of reactions, including nucleophilic substitutions, rearrangements, and cyclizations. It is also used in the synthesis of pharmaceuticals and agrochemicals. Overall, Trimethylsilyl trifluoromethanesulfonate is a versatile compound that plays a crucial role in the field of organic chemistry.
View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; Trimethylsilyl trifluoromethanesulfonate; 1.2 Synonyms; [(Trifluoromethane-sulfonyl)oxy]trimethylsilane CT3795 EINECS 248-565-4 Methanesulfonic acid, 1,1,1-trifluoro-, trimethylsilyl ester Methanesulfonic acid, trifluoro-, trimethylsilyl ester MFCD00000406 SILANE TMS-TRIFLATE TMS TRIFLATE TMSOTF TMS-OTf trifluoromethanesulfonic acid trimethylsilyl ester Trifluoromethanesulfonic acid trimethylsilylester trifluoromethanesulphonic acid trimethylsilyl ester TRIMETHYLSILYL TRIFLATE Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent] TRIMETHYLSILYL TRIFLUOROMETHANESULPHONATE trimethylsilyl trifluoromethane-sulphonate Trimethylsilyl trifluoromethylsulfonate trimethylsilyl trifluoromethylsulphonate Trimethylsllytrifluoromethanesulphonate; View all

1.3 CAS No.: 27607-77-8

1.4 CID: 65367

1.5 EINECS(EC#): 248-565-4

1.6 Molecular Formula: C4H9F3O3SSi (isomer)

1.7 Inchi: InChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3

1.8 InChIkey: FTVLMFQEYACZNP-UHFFFAOYSA-N

1.9 Canonical Smiles: C[Si](C)(C)OS(=O)(=O)C(F)(F)F

1.10 Isomers Smiles: C[Si](C)(C)OS(=O)(=O)C(F)(F)F

2. Properties

2.1 Density: 1.225

2.1 Melting point: 25°C

2.1 Boiling point: 140℃

2.1 Refractive index: 1.36-1.362

2.1 Flash Point: 25℃

2.1 Precise Quality: 221.99900

2.1 PSA: 51.75000

2.1 logP: 2.76830

2.1 Appearance: Clear slightly yellow liquid.

2.2 Storage: 2-8℃

2.3 Chemical Properties: clear colourless to light brown fuming liquid

2.4 Color/Form: Clear colorless to light brown

2.5 Water Solubility: REACTS

2.6 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.7 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 40 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 3 of 40 companies. For more detailed information, please visit ECHA C&L website

Of the 8 notification(s) provided by 37 of 40 companies with hazard statement code(s):

H226 (97.3%): Flammable liquid and vapor [Warning Flammable liquids]
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H335 (16.22%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P370+P378, P403+P233, P403+P235, P405, and P501; View all

3.2 Usage: Trimethylsilyl Trifluoromethanesulfonate is a trialkylsilyl triflate used as a catalyst in organic synthesis. Trimethylsilyl Trifluoromethanesulfonate is used in combination with boron trifluoride ethyl 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.

4. Safety and Handling

4.1 Symbol: GHS02, GHS05

4.1 Hazard Codes: C

4.1 Signal Word: Danger

4.1 Risk Statements: R10;R14;R34

4.1 Safety Statements: S16;S26;S36/37/39;S45;S8

4.1 Packing Group: III

4.1 Hazard Class: 3

4.1 Hazard Declaration: H226-H314

4.1 RIDADR: UN 2920

4.1 Caution Statement: P280-P305 + P351 + P338-P310

4.1 WGK Germany: 3

4.1 Sensitive: Moisture Sensitive

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H226 Flammable liquid and vapour H314 Causes severe skin burns and eye damage
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

27607-77-8Total: 27 Synthesis Route

99542-57-1

27607-77-8 244 Suppliers

Literatures:
Tacke, Reinhold; Link, Matthias; Zilch, Harald Chemische Berichte, 1985 , vol. 118, # 11 p. 4637 - 4640
Yield: ~97%

16393-88-7

27607-77-8 244 Suppliers

Literatures:
Fronda, Antonio; Maas, Gerhard Journal of Organometallic Chemistry, 1990 , vol. 391, # 3 p. 289 - 294
Yield: null

72658-09-4

27607-77-8 244 Suppliers

55453-09-3 1 Suppliers

Literatures:
Lin, Shuqiong; Bondar, Georgiy V.; Levy, Christopher J.; Collins, Scott Journal of Organic Chemistry, 1998 , vol. 63, # 6 p. 1885 - 1892
Yield: null

View all

8. Precursor and Product

precursor:

81290-20-2

2923-28-6

10416-59-8

18156-74-6

762-72-1

3385-94-2

72658-09-4

3908-55-2

65597-24-2

18163-07-0

99542-57-1

2794-60-7

18306-29-1

358-23-6

1493-13-6

107-46-0

75-77-4

5936-98-1

75-76-3

25436-07-1

14630-40-1

16393-88-7

76-05-1

97730-10-4

43112-38-5

333-27-7

View all

product :

115726-23-3

13735-81-4

58518-76-6

7449-74-3

28143-79-5

37471-46-8

17510-46-2

52119-18-3

32865-86-4

64821-69-8

102588-18-1

1833-53-0

6651-34-9

6651-39-4

38053-91-7

872-50-4

17242-85-2

75-38-7

102588-22-7

55991-66-7

1825-63-4

420-56-4

31928-64-0

10457-14-4

7288-28-0

6651-40-7

View all

9. Other Information

9.0 Usage: Trimethylsilyl trifluoromethanesulfonate is used to prepare powerful Lewis acid, difluoroboron triflate etherate in acetonitrile solvent. It is also used as a reagent in a Dieckmann-like cyclization of ester-imides and diesters. Further, it is used in the conversion of carbonyl compounds to their enol ethers. It is also employed for chemical glycosylation reactions. Its reactivity is similar to trimethylsilyl chloride and is also involved in organic synthesis.

9.1 Merck: 14,9719

9.2 BRN: 1868911

9.3 Chemical Properties: clear colourless to light brown fuming liquid

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

9.5 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.; View all

9.6 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.

9.7 Uses: Catalyst and silylating agent for organic syntheses.

10. Computational chemical data

Molecular Weight: 222.253g/mol
Molecular Formula: C₄H₉F₃O₃SSi
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 221.99937634
Monoisotopic Mass: 221.99937634
Complexity: 244
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 51.8
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgMYhAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAERQAAEAAAAAAABBCAAAAAAMAAAAAAHAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What Makes Trimethylsilyl Trifluoromethanesulfonate a Versatile Reagent in Organic Chemistry? Jun 23 2024
Introduction Trimethylsilyl trifluoromethanesulfonate is a widely utilized reagent in organic chemistry, known for its effectiveness in various synthetic transformations. This compound has garnered si..
How was Trimethylsilyl trifluoromethanesulfonate first synthesized? Jun 22 2024
Trimethylsilyl trifluoromethanesulfonate was first synthesized by Schmeisser et al. in 1970 and has since become a widely used silane reagent in organic synthesis due to its strong reactivity. Functio..
What are the key intermediates in the isomerisation of permethylated methyl d-glycopyranosides catalysed by Trimethylsilyl trifluoromethanesulfonate? May 09 2024
Research on the mechanism of isomerisation of permethylated methyl d-glycopyranosides catalysed by Trimethylsilyl trifluoromethanesulfonate has revealed that both cyclic and acyclic carbonyl ions play..
What are the Applications of Trimethylsilyl Trifluoromethanesulfonate in Organic Synthesis? Jun 28 2023
General Description Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is a trifluoromethanesulfonate compound with a trimethylsilyl R-group. It is commonly used in organic synthesis and exhibits simil..

12. Recommended Suppliers

Global230SuppliersView all >>

Tianjin Furun Tongda International Trade Co., LTD Diamond member

1YR

Products:Plastic particles, chemical products
Tel:+86-0-18032801167
Email:Nora@furuntongda.com

High quality Trimethylsilyl trifluoromethanesulfonate CAS 27607-77-8 in stock

Purity:99%Packing: 200kg/bag FOB
Price: 23 USD/kg
Time: 2024/11/15

Inquire

Hubei Jiutian Bio-medical Technology Co., Ltd Diamond member

5YRS

Products:electronic chemicals; pharmaceutical intermediates;pesticide intermediates;ultraviolet absorbent; food additives
Tel:86-173-54350817
Email:Ryan@jiutian-bio.com

Trimethylsilyl trifluoromethanesulfonate