How is triflic acid made?
How is triflic acid made?
Trifluoromethanesulfonic acid is produced industrially by electrochemical fluorination (ECF) of methanesulfonic acid: CH3SO3H + 4 HF → CF3SO2F + H2O + 3 H. The resulting CF3SO2F is hydrolyzed, and the resulting triflate salt is preprotonated. Triflic acid is purified by distillation from triflic anhydride.
What is TfOH?
TfOH or triflic acid (trifluoromethanesulfonic acid), is often used in organic synthesis as an acid catalyst. Having a pKa of about -15 it is considered a superacid and is among the strongest of acids.
Is triflic acid organic?
The triflate anion is widely used as intermediate in organic synthesis, since it is an excellent leaving group (up to 30,000 times more effective than tosylate)….Chemical categories.
| Chemical category | Chemical family | Chemical product |
|---|---|---|
| Fluorine derivatives | Fluorinated Chemicals | Triflic acid |
How strong is triflic acid?
Trifluoromethanesulfonic acid, also known as triflic acid or TfOH, is a sulfonic acid with the chemical formula CF3SO3H . It is often regarded as one of the strongest acids, and is one of a number of so-called “superacids”. It is about 1000 times stronger than sulfuric acid.
How do you make a triflate?
Triflate salts They can be obtained directly from triflic acid and the metal hydroxide or metal carbonate in water. Alternatively, they can be obtained from reacting metal chlorides with neat triflic acid or silver triflate, or from reacting barium triflate with metal sulfates in water: MCln + n HOTf → M(OTf)n + n HCl.
How do you use triflic anhydride?
Triflic anhydride is useful for converting ketones into enol triflates. In a representative application, is used to convert an imine into a NTf group. It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.
What does Gtfoh mean in text?
GTFOH
| Acronym | Definition |
|---|---|
| GTFOH | Get the Fudge Outta Here (polite form) |
How do you store triflic acid?
Containers which are opened must be carefully resealed under an inert atmosphere, and kept upright to prevent leakage. Recommended storage temperatures: – Triflic acid: Do not store above temperatures of 25°C. – Fluorosulfonic acid: 2–8oC – Chlorosulfonic acid: Do not store above temperatures of 25°C.
What is the PH of Fluorosulfuric acid?
1.8. Fluorosulfuric acid (HSO3F) is one of the strongest Brønsted acids known, with H0 (Hammett’s acidity function) = −15.1.
What is triflate used for?
A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in SN2 reactions, they must be stored in conditions free of nucleophiles (such as water).
How do you quench triflic anhydride?
The reaction is stirred at room temperature for 18h, under an inert atmosphere. The reaction is quenched by addition of 100 mL of water and the product is extracted with dichloromethane (3 x 120 mL). The organic phase is dried over MgSO4, filtered and concentrated under reduced pressure.
