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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]
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 ...
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]
Its pK a value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3 (relative to the pK a value of 2,4,6-trinitrophenol (picric acid), anchored to zero to crudely approximate the aqueous pK a scale [2]), making it more acidic than triflic acid (pK a MeCN = 0.70, pK a DCE ...
The trifluoromethyl group is a functional group that has the formula-CF 3. The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluoromethane H– CF 3, 1,1,1-trifluoroethane H 3 C – CF 3, and hexafluoroacetone F 3 C –CO– CF 3.
The reaction that will proceed is a bimolecular nucleophilic substitution reaction (SN2) (Figure 2). The nitrogen atom from the amino-group of 2-amino-5-tert-butyl-1,3,4-thiadiazole will attack the sulfur atom of benzene-sulfonyl chloride, leading to a chloride ion being removed from the benzenesulfonyl chloride.
Benzotrichloride is a poorly water-soluble, clear to yellowish liquid with a penetrating odor. It hydrolyzes rapidly to benzoic acid and hydrochloric acid with a half life of about 2.4 minutes, thus making the compound unstable in the presence of water. [2]
[6] [3] MSF, which is a liquid at room temperature, has a vapor pressure of 19.2 mmHg, slightly more volatile than water which has a vapor pressure of 18.8 mmHg at 21 °C. This vapor has an LCt 50 (lethal concentration, 50% death rate in a given time) in rats of between 4 and 5 parts per million (ppm) during one hour of exposure or between 1 ...