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Trifluoromethanesulfonyl chloride (or triflyl chloride, CF3SO2Cl) can be used in a highly efficient method to introduce a trifluoromethyl group to aromatic and heteroaromatic systems, including known pharmaceuticals such as Lipitor. The chemistry is general and mild, and uses a photoredox catalyst and a light source at room temperature. [27]
However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, [3] acetonitrile, or pyridine. [4] Tf 2 O + NaN 3 → TfN 3 + NaOTf (Tf = CF 3 SO 2) An alternative route starts from imidazole-1-sulfonyl azide. [5]
The sulfonyl functional group (RS(O) 2 R') has become an important electron-withdrawing group for modern organic chemistry. α-Sulfonyl carbanions may be used as nucleophiles in alkylation reactions, Michael-type additions, and other processes. [3] After having served their synthetic purpose, sulfonyl groups are often removed.
A derivative of trifluorotoluene, 3-aminobenzotrifluoride, is the precursor to the herbicide fluometuron. [3] It is synthesized via nitration followed by reduction to meta-H 2 NC 6 H 4 CF 3. This aniline is then converted to the urea. Flumetramide (6-[4-(trifluoromethyl)phenyl]morpholin-3-one), a skeletal muscle relaxant, is also prepared from ...
For example, n-butyl triflate can be written as CH 3 CH 2 CH 2 CH 2 OTf. The corresponding triflate anion, CF 3 SO − 3, is an extremely stable polyatomic ion; this comes from the fact that triflic acid (CF 3 SO 3 H) is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest acids known.
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF 3 SO 3 H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. [2] [3] It is a hygroscopic, colorless, slightly viscous liquid and is soluble in ...
3,4,5-Trimethoxybenzaldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including trimethoprim, [1] [2] cintriamide, roletamide, trimethoquinol (aka tretoquinol), and trimazosin as well as some psychedelic phenethylamines.
Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf 3 CH) is an organic superacid. It is one of the strongest known carbon acids and is among the strongest Brønsted acids in general, with an acidity exceeded only by the carborane acids .