How stable is trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride (triflic anhydride),abbreviated Tf2O, is generally considered stable under normal conditions but does have some important handling and storage considerations:

1. Reactivity: While stable in dry conditions, triflic anhydride is highly reactive, especially with water and alcohols. When it comes into contact with moisture, it hydrolyzes to form trifluoromethanesulfonic acid (triflic acid), which can lead to the release of heat and potentially dangerous reactions if not properly controlled.

2. Temperature Sensitivity: Tf2O should be stored in cool, dry environments. High temperatures may accelerate decomposition or unwanted reactions.

3. Inert Atmosphere: When working with it, an inert atmosphere (like nitrogen or argon) is recommended to prevent Tf2O from reacting with moisture or air. This is especially important during storage and transfer.

4. Corrosiveness: It’s highly corrosive to skin, eyes, and mucous membranes, and it can damage materials like metals or plastics if spilled.

5. Stability in Sealed Containers: In tightly sealed containers, triflic anhydride can remain stable for a longer period of time, provided it is kept away from any moisture sources.

If you’re planning to handle or sell this product, proper storage, and safety measures are key to ensuring its stability and preventing hazards.