358-23-6 | Trifluoromethanesulfonic anhydride

CAS:358-23-6 | Trifluoromethanesulfonic anhydride ,Description

Trifluoromethanesulfonic anhydride (TFMSA) is a strong acid anhydride, with a wide range of applications in both organic and inorganic chemistry. It is a versatile reagent, and is used in a variety of synthetic methods and processes. It is also used in many scientific research applications, such as the synthesis of novel compounds and the study of biochemical and physiological effects. In 
 

Scientific Research Applications

Catalyst in Acylation

Trifluoromethanesulfonic anhydride is used as a catalyst in the acylation of alcohols with acid anhydrides. Its high catalytic activity is effective for acylating primary, secondary, and tertiary alcohols, including those that are sterically hindered. This process is particularly useful for macrolactonization of omega-hydroxy carboxylic acids (Ishihara et al., 1996).

Activation in Organic Synthesis

Trifluoromethanesulfonic anhydride acts as a strong electrophilic activator in synthetic organic chemistry, leading to the formation of a versatile triflate intermediate. This intermediate is highly reactive and can be used in a variety of nucleophilic trapping reactions to produce novel compounds, particularly in amide, sulfoxide, and phosphorus oxide chemistry (Huang & Kang, 2021).

Electrophilic Nitrating Agent

Trifluoromethanesulfonic anhydride is a highly effective electrophilic nitrating agent for a series of aromatics, yielding high yields under mild conditions. Its use in nitration showcases its versatility in different chemical reaction pathways (Olah et al., 1992).

Self-Immolative Reduction of Sulfoxides

In the absence of added nucleophilic species, trifluoromethanesulfonic anhydride, when used with sulfoxides, results in the reduction of the sulfoxide to a sulfane. This demonstrates its utility in creating unique chemical transformations (Macé et al., 2010) .

Formation of Highly Electrophilic Intermediates

Trifluoromethanesulfonic anhydride is used in the electrophilic activation of amides, forming highly electrophilic and reactive intermediates. These intermediates can engage in various reaction pathways, showcasing the compound's ability to facilitate diverse chemical transformations (Kaiser & Maulide, 2016).

Generation of Glycosyl Triflates

Trifluoromethanesulfonic anhydride, in combination with other reagents, can activate thioglycosides to form glycosyl triflates. These triflates are then easily converted to glycosides, demonstrating its utility in complex carbohydrate chemistry (Crich & Smith, 2001).

Synthesis of Amides from Ketoximes

The compound is successfully used as a reagent in the Beckmann rearrangement for the conversion of ketoximes into amides. This application highlights its efficiency in synthesizing a variety of amide compounds (Kalkhambkar & Savanur, 2015).

Trifluoromethylation Reagent

Trifluoromethanesulfonic anhydride is used as a cost-efficient and practical reagent for trifluoromethylation, particularly in the development of (hetero)arenes. Its low cost and abundant availability make it a favorable choice for synthesizing trifluoromethylated compounds (Ouyang et al., 2018).

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