Trifluoromethanesulfonic Anhydride | Tf2O | CAS: 358-23-6 | High Purity ! Manufacturer

Description

Product Name: Trifluoromethanesulfonic Anhydride Tf2O CAS: 358-23-6 High Purity

CAS: 358-23-6

Packages: 50 Kg

Main use: an intermediate in the pharmaceutical industry for the production of proteins, glycosides, and vitamins; a catalyst for Friedel-Crafts benzylation and cyclohexylation reactions.

Availability : In Stock

What is Trifluoromethanesulfonic Anhydride(Tf2O)?

Trifluoromethanesulfonic anhydride( Tf2O), also known as triflic anhydride, is an electrophilic reagent that is an efficient source of trifluoromethyl. It is commonly used in organic chemistry to convert oxygen-containing compounds to triflates and for the electrophilic activation and subsequent conversion of amides, sulfoxides, and phosphorus oxides.It is a commonly used intermediate in the pharmaceutical industry, and it is widely used in the synthesis of sterols, proteins, antibiotics, anticancer drugs, and nucleosides.

Certificate of Analysis – High Purity !  99.5 %

Trifluoromethanesulfonic Anhydride | Tf2O | CAS: 358-23-6

What are applications of Trifluoromethanesulfonic Anhydride(Tf2O) ?

Trifluoromethanesulfonic anhydride (Tf2O) is a powerful electrophilic reagent used in organic synthesis for triflation reactions, activating functional groups, and as a catalyst. Its uses include converting alcohols to triflates, activating amides, sulfoxides, and phosphorus oxides, synthesizing complex molecules like polysaccharides and tetrazoles, and serving as a polymerization initiator. It is also used as a building block for active ingredients in crop protection and to introduce the trifluoromethyl group (𝐶𝐹3) into molecules. 

• Triflation: Converts oxygen-containing compounds like alcohols and phenols into the highly reactive triflate esters (OTf).
• Activation and transformation:
  • • Activates amides, sulfoxides, and phosphorus oxides, making them susceptible to nucleophilic attack.
    • Can be used for the preparation of substituted tetrazoles from secondary amides.

• Synthesis of complex molecules:
  • • Acts as a catalyst for glycosylation reactions to synthesize polysaccharides and other complex carbohydrates.
    • Used in the stereoselective synthesis of compounds like mannosazide methyl uronate donors.
    • Serves as a reagent in cyclization reactions like the Bischler−Napieralski cyclization.

• Introduction of functional groups:
  • • Introduces the triflyl group (CF3SO2) into various molecules.
    • Used for trifluoromethylation and trifluoromethylthiolation.

• Catalysis:
  • • Serves as a Lewis acid catalyst for reactions such as Friedel-Crafts acylations and other cyclizations.
    • Can initiate cationic polymerization, particularly for certain monomers like vinyl ethers.

• Industrial applications:
  • Used as a building block for the active ingredients in products like herbicides and other crop protection agents.
  • A catalyst in the plastics industry for polymerization and oligomerization

Q1. What is Trifluoromethanesulfonic Anhydride (Tf₂O) and what is it used for?

A: Trifluoromethanesulfonic Anhydride (Tf₂O) is a highly reactive reagent commonly used in organic synthesis. It is primarily employed as a powerful triflating agent to convert alcohols, phenols, and enolates into corresponding triflates, which are excellent leaving groups for cross-coupling reactions (e.g., Suzuki, Heck, Stille). It is also widely used in the synthesis of pharmaceuticals, agrochemicals, and specialty polymers.

Q2. How should Tf₂O be stored and handled safely?

A: Tf₂O is moisture-sensitive and corrosive. It should be stored in a tightly sealed, inert (e.g., argon or nitrogen) atmosphere in a cool, dry place away from water, alcohols, and bases. Always handle in a well-ventilated fume hood with appropriate PPE (gloves, safety goggles, lab coat). Avoid inhalation and contact with skin; in case of spill, neutralize with a non-combustible absorbent (e.g., vermiculite) and avoid water.

Q3. Is Trifluoromethanesulfonic Anhydride dangerous or toxic?

A: Yes, Tf₂O is classified as a corrosive and lachrymatory substance. It can cause severe skin burns, eye damage, and respiratory irritation. Contact with water releases triflic acid (trifluoromethanesulfonic acid), which is highly corrosive. It is also considered a potential sensitizer. Always follow the safety data sheet (SDS) and use appropriate engineering controls.

Q4. What is the difference between Tf₂O and triflic acid (TfOH)?

A: Tf₂O is the anhydride of triflic acid (TfOH). The key difference is reactivity: Tf₂O is a much stronger electrophile and a better triflating agent, while TfOH is a strong protic acid. Tf₂O reacts with water or alcohols to generate TfOH, which can lead to unwanted side reactions if moisture is present. For triflation reactions, Tf₂O is typically preferred over TfOH.

Q5. Can Tf₂O be used in peptide or carbohydrate chemistry?

A: Yes, Tf₂O is used in peptide chemistry for the activation of carboxylic acids (forming mixed anhydrides) and in carbohydrate chemistry for the activation of anomeric hydroxyl groups. However, due to its high reactivity, mild conditions and careful control of stoichiometry are required to avoid racemization or over-reaction. Its use in these fields is valued when strong leaving groups are necessary for difficult couplings.

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