A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl. These reagents are useful because, unlike related Grignard reagents and organolithium reagents, they react with organic halides to replace the halide group with an R group (the Corey–House reaction). Such displacement reactions allow for the synthesis of complex products from simple building blocks.
In organosulfur chemistry, a sulfonate is a salt or ester of a sulfonic acid. It contains the functional group R−S(=O)2−O−, where R is an organic group. Sulfonates are the conjugate bases of sulfonic acids. Sulfonates are generally stable in water, non-oxidizing, and colorless. Many useful compounds and even some biochemicals feature sulfonates.
In organic chemistry, triflate, is a functional group with the formula R−OSO2CF3 and structure R−O−S(=O)2−CF3. The triflate group is often represented by −OTf, as opposed to −Tf, which is the triflyl group, R−SO2CF3. For example, n-butyl triflate can be written as CH3CH2CH2CH2OTf.
Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.
Phosphorus pentoxide is a chemical compound with molecular formula P4O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant and dehydrating agent.
Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO3F. It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, H2SO4, substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow.
Scandium trifluoromethanesulfonate, commonly called scandium triflate, is a chemical compound with formula Sc(SO3CF3)3, a salt consisting of scandium cations Sc3+ and triflate SO
3CF−
3 anions.
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.
Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.
sec-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.
Methyl trifluoromethanesulfonate, also commonly called methyl triflate and abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It is a colourless liquid which finds use in organic chemistry as a powerful methylating agent. The compound is closely related to methyl fluorosulfonate (FSO2OCH3). Although there has yet to be a reported human fatality, several cases were reported for methyl fluorosulfonate (LC50 (rat, 1 h) = 5 ppm), and methyl triflate is expected to have similar toxicity based on available evidence.
Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et2NSF3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds. The compound is colourless; older samples assume an orange colour.
Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers. This colourless gas is the epoxide of hexafluoropropylene, that is fluorinated analog of propylene oxide, HFPO is produced by DuPont and 3M and as a precursor to the lubricant Krytox and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.
Trifluoromethyltrimethylsilane (known as Ruppert-Prakash reagent, TMSCF3) is an organosilicon compound with the formula CF3Si(CH3)3. It is a colorless liquid. The compound is a reagent used in organic chemistry for the introduction of the trifluoromethyl group. The compound was first prepared in 1984 by Ingo Ruppert and further developed as a reagent by G. K. Surya Prakash.
In organic chemistry, the triflyl group is a functional group with the formula R−SO2CF3 and structure R−S(=O)2−CF3. The triflyl group is often represented by –Tf.
Pentacarbonylhydridomanganese is an organometallic compound with formula HMn(CO)5. This compound is one of the most stable "first-row" transition metal hydrides.
Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.
Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3COOOH. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.
Martin's sulfurane is the organosulfur compound with the formula Ph2S[OC(CF3)2Ph]2 (Ph = C6H5). It is a white solid that easily undergoes sublimation. The compound is an example of a hypervalent sulfur compound called a sulfurane. As such, the sulfur adopts a see-saw structure, with a lone pair of electrons as the equatorial fifth coordinate of a trigonal bipyramid, like that of sulfur tetrafluoride (SF4). The compound is a reagent in organic synthesis. One application is for the dehydration of a secondary alcohol to give an alkene:
