Trifluoromethanesulfonic Anhydride 358-23-6 (CF₃SO₂)₂O

Trifluoromethanesulfonic anhydride, also known as triflic anhydride (CAS No: 358-23-6),abbreviated Tf2O, is an important chemical compound used in organic synthesis. Its molecular structure consists of a trifluoromethyl group (CF₃) attached to a sulfonic anhydride group (SO₂), making it a highly reactive and electrophilic compound. With a density of approximately 1.677 g/cm³, triflic anhydride is commonly used to introduce the trifluoromethanesulfonyl group into organic molecules, which can enhance their reactivity and stability. This compound, also referred to as triflic acid anhydride, is valuable in pharmaceutical, polymer, and fine chemical industries, where it plays a key role in the synthesis of triflates, which are important intermediates in various chemical reactions.Ecovia, as an advanced sales and service provider in China, provides high purity and high stability of Trifluoromethanesulfonic Anhydride for you, if you have any questions, you can contact us!

  Triflic Anhydride Uses  

Trifluoromethanesulfonic anhydride (triflic anhydride) has several important uses in chemical synthesis, particularly in the pharmaceutical, fine chemicals, and polymer industries. Here are some key applications:

Chemical Synthesis Reagent

Introduction of Trifluoromethanesulfonyl (Triflyl) Group: Tf2O is widely used to introduce the trifluoromethanesulfonyl group (–SO2CF3) into organic compounds. This is valuable for modifying the electronic properties of molecules and improving their reactivity.
Electrophilic Substitution Reactions: It is used in electrophilic substitution reactions, such as the preparation of aryl triflates (aromatic compounds with a trifluoromethanesulfonyl group), which are valuable intermediates in organic synthesis and in pharmaceutical production.

Pharmaceutical Industry

Synthesis of Active Pharmaceutical Ingredients (APIs): Triflic anhydride is often used in the synthesis of various pharmaceutical compounds due to its ability to form triflate esters with alcohols and phenols, improving solubility and bioavailability.
 Medicinal Chemistry: It is involved in the creation of drug candidates, especially in reactions where fluorination is required or when modifying the functional groups of organic molecules.

Polymerization Initiator

Tf2O can be used in polymerization processes, particularly in the synthesis of fluoropolymers like polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF). The triflyl group can help introduce functionality that improves the properties of these polymers, such as chemical resistance and stability at high temperatures.

Electrophilic Fluorination

Tf2O is sometimes used in electrophilic fluorination reactions, where the trifluoromethanesulfonyl group can be exchanged with other groups, contributing to the synthesis of fluorinated organic compounds that are important for various industrial applications.

Synthesis of Catalysts and Ligands

It can be used in the synthesis of fluorinated ligands for metal-catalyzed reactions. The triflyl group enhances the electrophilic character of ligands, making them more effective in reactions like cross-coupling or hydrogenation.

Water-Free Reactions

Dehydration Agent: Triflic anhydride is also used as a drying agent in reactions where moisture must be excluded to prevent hydrolysis or unwanted side reactions.

Synthesis of Triflate Salts

Triflic anhydride is often used to create triflate salts, which are superior electrophiles in nucleophilic substitution reactions. These salts are valuable in organometallic chemistry and synthetic chemistry for constructing various organic compounds.

Polymer Processing and Functionalization

In polymer functionalization, triflic anhydride is used to add specific functional groups to polymers, which can improve their performance, such as enhancing chemical resistance, solubility, or stability in extreme conditions.

Summary of Uses:

1. Synthesis of triflate esters (key intermediates in organic and pharmaceutical synthesis)

2. Fluorination and modification of organic compounds

3. Polymerization processes and functionalization of polymers

4. Dehydration and drying agent in chemical reactions

5. Preparation of active pharmaceutical ingredients (APIs)

6. Electrophilic fluorination for fluorinated compounds

7. Catalyst and ligand synthesis for metal-catalyzed reactions

These applications are a significant part of how triflic anhydride is used across different industries.

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