333-27-7

Usage

Uses

Used in Chemistry:
Methyl trifluoromethanesulfonate is used as a powerful methylating reagent for various chemical reactions. It can efficiently transfer a methyl group to a wide range of substrates, including alcohols, phenols, and carboxylic acids.
Used in Suzuki Reaction:
Methyl trifluoromethanesulfonate is used in the Suzuki reaction, a widely used cross-coupling reaction for the formation of carbon-carbon bonds. It serves as a catalyst to facilitate the reaction between an organoboron compound and an organic halide, leading to the formation of the desired product.
Used in Conversion of Amines:
Methyl trifluoromethanesulfonate is used in the conversion of amines to methyl ammonium triflates. This conversion is useful for the synthesis of various organic compounds and can be employed in the preparation of pharmaceuticals and agrochemicals.
Used in Synthesis of 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate:
Methyl trifluoromethanesulfonate was used in the synthesis of 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate, a compound with potential applications in various fields, such as pharmaceuticals and materials science.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Methyl trifluoromethanesulfonate is sensitive to heat. . Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Methyl trifluoromethanesulfonate emits toxic fumes.

Fire Hazard

Methyl trifluoromethanesulfonate is combustible.

Purification Methods

Methyl trifluoromethanesulfonate (methyl triflate) [333-27-7] M 164.1, b 97 -97.5o/736mm, 9 9o/~760mm, 100-102o/~760mm, d 4 1.496, n D 1.3238. It is a strong methylating agent but is corrosive and POISONOUS. Fractionate it carefully and collecting the middle fraction (use an efficient fume cupboard) and keep away from moisture. It is a POWERFUL ALKYLATING AGENT and a strong IRRITANT. [IR: Gramstad & Haszeldine J Chem Soc 173 1956 , J Chem Soc 4069 1957 .] Trifluoromethanesulfonic acid (triflic acid) [1493-13-6] M 151.1, boils higher (b 162o/atm), has a pKa of 3.10, and is TOXIC and hygroscopic. [Hansen J Org Chem 30 4322 1965, Kurz & El-Nasr J Am Chem Soc 104 5823 1982, Beilstein 3 IV 34.]

InChI:InChI=1/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 920-68-3 heptamethyldisilazane 
• 14848-27-2 nitrosonium trifluoromethanesulfonate 
• 597-07-9 N,N-dimethyl-O,O-dimethylphosphoramidate 
• 64294-70-8 methylmethoxydiphenoxyphosphonium triflate 
• 74-88-4 methyl iodide 
• 100571-62-8 methylazoxy triflate 
• 75-09-2 dichloromethane 
• 65597-24-2 Chlorine(I) trifluoromethanesulfonate 
• 616-38-6 carbonic acid dimethyl ester 
• 34557-54-5 methane 

Downstream Products

• 540-67-0 ethyl methyl ether 
• 425-75-2 trifluoromethanesulfonic acid ethyl ester 
• 1493-13-6 trifluorormethanesulfonic acid 
• 64294-67-3 phenylmethyldimethoxyphosphonium trifluoromethanesulfonate 
• 64294-69-5 C₁₄H₁₆OP⁽¹⁺⁾*CF₃O₃S^(1-) 
• 2282-84-0 methyl 2,4,6-trimethylbenzoate 
• 64294-70-8 methylmethoxydiphenoxyphosphonium triflate 
• 54758-27-9 Trifluoro-methanesulfonate(4-heptyloxysulfonyl-phenyl)-trimethyl-ammonium; 
• 54758-25-7 Trifluoro-methanesulfonatetrimethyl-[4-(1-methyl-heptyloxysulfonyl)-phenyl]-ammonium; 
• 61165-44-4 Trifluoro-methanesulfonatetrimethyl-(4-octyloxysulfonyl-phenyl)-ammonium; 
• 54758-23-5 Trifluoro-methanesulfonatetrimethyl-[4-(2-methyl-heptyloxysulfonyl)-phenyl]-ammonium; 
• 72315-64-1 C₁₉H₁₈PSe⁽¹⁺⁾*CF₃O₃S^(1-) 
• 61165-46-6 Trifluoro-methanesulfonate(4-butoxysulfonyl-phenyl)-trimethyl-ammonium; 
• 61165-48-8 Trifluoro-methanesulfonate(4-sec-butoxysulfonyl-phenyl)-trimethyl-ammonium; 

Relevant academic research and scientific papers

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.

METHODS FOR FUNCTIONALIZATION HYDROCARBONS

In one aspect, the disclosure relates to a method for functionalizing hydrocarbons. In a further aspect, the method involves heating a hydrocarbon with a composition having an acid and an oxidant. In other aspects, the composition can further include an iodine-based compound and/or a compound having formula AaXn. In any of these aspects, the oxidant can be regenerated in situ or in a separate regeneration step. Also disclosed are functionalized hydrocarbons produced by the disclosed method. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.

Tuning the biological activity of cationic anthraquinone analogues specifically toward Staphylococcus aureus

Development of new antibacterial agents against drug resistant bacteria is an imminent task, especially against methicillin-resistant Staphylococcus aureus (MRSA). While MRSA can still be treated with broad spectrum antibiotics, the use of which often leads to the disruption of normal microbial flora leading to Clostridium difficile infection (CDI). Herein, a new class of antibacterial agent, cationic anthraquinone analogues specifically against MRSA, has been developed. Through the variation and optimization of substituents, these agents are selective toward MRSA, and not Gram negative bacteria which may avoid the problem of CDI. In addition, newly discovered lead compounds also show significantly reduced cytotoxicity against normal mammalian cells than cancerous cells. This interesting finding can alleviate the toxicity and side effect problems often associate with the use of antibiotics.

COMPOUND FOR SPECIFICALLY BINDING TO AMYLOID ?-PROTEIN

Provided is a compound for specifically binding to amyloid β-protein. The compound has thereon a nuclide with a large thermal neutron capture cross section and the compound is capable of specifically binding to the amyloid β-protein. The property of the compound allows it to be used in conjunction with a neutron capture therapy device to eliminate amyloid β-protein. Similarly, when the compound is labelled with radioactive element 11C, the compound can also be used in conjunction with PET/CT for determining the part of the brain where amyloid β-protein is deposited, for diagnosing Alzheimer's disease. Also disclosed is a preparation process for the compound. The beneficial effect of the present disclosure is to make the therapy and diagnosis of Alzheimer's disease more targeted by providing the compound for specifically binding to amyloid β-protein.

Arylation of diorganochalcogen compounds with diaryliodonium triflates: Metal catalysts are unnecessary

Diaryliodonium triflates transfer an aryl group to the chalcogen atom of organic sulfides, selenides, and tellurides (but not ethers), in the absence of transition-metal catalyst, simply upon heating in chloroform or dichloroethane solution.

A convenient synthesis of triflate anion ionic liquids and their properties

A solvent- and halogen-free synthesis of high purity triflate ionic liquids via direct alkylation of organic bases (amines, phosphines or heterocyclic compounds) with methyl and ethyl trifluoromethanesulfonate (methyl and ethyl triflate) has been developed. Cheap and non-toxic dimethyl and diethyl carbonate serve as source for the methyl and ethyl groups in the preparation of methyl and ethyl triflate by this invented process. The properties of ionic liquids containing the triflate anion are determined and discussed.

Protonation and alkylation of organophosphorus compounds with trifluoromethanesulfonic acid derivatives

Protonation (alkylation) of triphenylphosphine, triethylphosphite, triphenylphosphine oxide, triethylphosphate, hexamethylphosporamide, and dimethylphosphite with trifluoromethanesulfonic acid, its bisimide, and methyl ester was studied and the corresponding 1H, 13C, 19F, 31P NMR spectra were analyzed.

Synthesis of azide-alkyne fragments for 'click' chemical applications. formation of chiral 1,4-disubstituted-(β-alkyl) γ- 1,2,3-triazole scaffolds from orthogonally protected chiral β-alkyl-trialkylsilyl γ- Pentynyl azides and chiral β-alkyl γ- Pentynyl-alcohols

A library of chiral γ-pentynyl alcohols and γ-pentynyl azides was made using the SuperQuat auxiliary. Coupling of the free alkynes with the azides by Huisgen 1,3-dipolar cycloaddition provided chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as possible peptidomimetic compounds.

α-aminoboronic acids prepared by novel synthetic methods

The present invention relates to a novel class of α-aminoboronic acids of Formula (V), which are useful as intermediates in synthetic processes for inhibitors of the serine proteases, leukocyte elastase, pancreatic elastase, cathepsin G, and chymotrypsin. More specifically, the α-aminoboronic acids are useful as intermediates for the synthesis of Hepatitis C Virus (HCV) protease inhibitors. This invention also generally relates to novel methods for the preparation of α-aminoboronic acids.