34310-29-7

Usage

Uses

Used in Chemical Synthesis:
N-Methyltrifluoromethanesulfonamide is utilized as a strong and non-nucleophilic base for facilitating various chemical reactions. Its role in these processes is critical due to its ability to act as a source of the trifluoromethyl cation, which is a key intermediate in the synthesis of a multitude of compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-Methyltrifluoromethanesulfonamide is employed as a reagent for the fluorination of organic compounds. This is particularly valuable in the development of new drugs, as the introduction of fluorine atoms can significantly alter the pharmacokinetic and pharmacodynamic properties of drug candidates, potentially enhancing their efficacy and safety.
Used in Agrochemical Production:
Similarly, in agrochemicals, N-Methyltrifluoromethanesulfonamide is used to introduce fluorine into organic molecules, which can improve the performance characteristics of these compounds, such as their stability, bioavailability, and target specificity in agricultural applications.
Used in Specialty Chemicals and Materials Manufacturing:
N-Methyltrifluoromethanesulfonamide is also integral in the manufacturing process of specialty chemicals and materials, where its unique properties can be harnessed to create products with specific attributes required for various high-performance applications.
Given the strong basic and nucleophilic nature of N-Methyltrifluoromethanesulfonamide, it is imperative that it is handled with caution, employing proper safety protocols to mitigate any potential risks associated with its use.

Upstream product

• 421-83-0 trifluoromethane sulfonyl chloride 
• 74-89-5 methylamine 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 593-51-1 methylamine hydrochloride 

Downstream Products

• 130061-49-3 Benzoic acid 3-(methyl-trifluoromethanesulfonyl-amino)-butyl ester 
• 129990-96-1 (R)-(-)-3-<(N-methyl-N-trifluoromethanesulfonyl)amino>-1-butanol benzoate 
• 129991-11-3 (S)-(+)-3-<(N-methyl-N-trifluoromethanesulfonyl)amino>-1-butanol benzoate 
• 51029-13-1 N-benzyl-N-methyl triflamide 

Relevant academic research and scientific papers

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

Sulfoxide ligand metal catalyzed oxidation of olefins

The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

Photoredox-Catalyzed Site-Selective α-C(sp3)?H Alkylation of Primary Amine Derivatives

The synthetic utility of tertiary amines to oxidatively generate α-amino radicals is well established, however, primary amines remain challenging because of competitive side reactions. This report describes the site-selective α-functionalization of primary amine derivatives through the generation of α-amino radical intermediates. Employing visible-light photoredox catalysis, primary sulfonamides are coupled with electron-deficient alkenes to efficiently and mildly construct C?C bonds. Interestingly, a divergence between intermolecular hydrogen-atom transfer (HAT) catalysis and intramolecular [1,5] HAT was observed through precise manipulation of the protecting group. This dichotomy was leveraged to achieve excellent α/δ site-selectivity.

C-H to C-N Cross-Coupling of Sulfonamides with Olefins

Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.

N-sulfonylaminocarbonyl containing compounds

Compounds having two reactive functional groups are described that can be used to provide a connector group between a substrate and an amine-containing material. The first reactive functional group can be used to provide attachment to a surface of a subst

Use of the Mitsunobu reaction in the synthesis of polyamines

The Mitsunobu reaction has been used in the synthesis of polyamine analogues. The synthesis of the (R,R), (S,S) and meso-isomers of a tetraamine are described. The chemistry was used to synthesize a fluorinated polyamine analog and a hexaamine.

Process for preparing amides by reaction in presence of molecular sieve

There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.