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Preparation of the trifluoromethyltrimethylsilane was reported by Ingo Ruppert in 1984. [11] In 1989, Prakash and Olah first reported activation of TMSCF 3 by fluoride to perform nucleophilic trifluoromethylation of carbonyl compounds. [12]
Trifluoromethyltrimethylsilane (known as Ruppert-Prakash reagent, TMSCF 3) is an organosilicon compound with the formula CF 3 Si(CH 3) 3.It is a colorless liquid. The compound is a reagent used in organic chemistry for the introduction of the trifluoromethyl group.
Two other isomers are also known: 2-trifluoromethylbenzaldehyde and 3-trifluoromethylbenzaldehyde. These compounds are derivatives of benzaldehyde with trifluoromethyl substituents. The CF 3 group enhances the electrophilicity of the formyl group and provides a label for analysis by fluorine-19 nuclear magnetic resonance spectroscopy.
The typical impurity in triflic anhydride is triflic acid, which is also a colorless liquid. Samples of triflic anhydride can be assayed by 19 F NMR spectroscopy: −72.6 ppm [8] vs. −77.3 for TfOH (std CFCl 3).
The name 1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide is also an unambiguous IUPAC-acceptable name, though the symmetry of the molecule is not apparent from this construction. See also
Colorless liquid Density: 1.5±0.1 g/cm 3: Melting point-110.64 ... trifluoromethanol can be prepared from trifluoromethyl hypochlorite and hydrogen chloride: CF
For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst: [2] PhX + CF 3 I → PhCF 3 (where X = I, Br) Industrial production is done by reacting benzotrichloride with hydrogen fluoride in a pressurized reactor. [3] PhCCl 3 + 3 HF → ...
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