Triphenylphosphine Complexes
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Triphenylphosphine Complexes
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether. Preparation and structure Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium: :PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl Triphenylphosphine crystallizes in triclinic and monoclinic modification. In both cases, the molecule adopts a pyramidal structure with propeller-like arrangement of the three ...
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International Union Of Pure And Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. IUPAC's executive director heads this administrative office, currently Greta Heydenrych. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee ...
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Organic Synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the general subject of organic synthesis, there are many different types of synthetic routes that can be completed including total synthesis, Enantioselective synthesis, stereoselective synthesis, automated synthesis, and many more. Additionally, in understanding organic synthesis it is necessary to be familiar with the methodology, techniques, and applications of the subject. Total synthesis A total synthesis refers to the complete chemical synthesis of molecules from simple, Precursor (chemistry), natural precursors. Total synthesis is accomplished either via a linear or convergent approach. In a Linear synthesis, ''linear'' synthesis—often adequate for simple structures—several steps are performed sequentially until the molecule is com ...
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Sulfur
Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with the chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature. Sulfur is the tenth most abundant element by mass in the universe and the fifth most common on Earth. Though sometimes found in pure, native form, sulfur on Earth usually occurs as sulfide and sulfate minerals. Being abundant in native form, sulfur was known in ancient times, being mentioned for its uses in ancient India, ancient Greece, China, and ancient Egypt. Historically and in literature sulfur is also called brimstone, which means "burning stone". Almost all elemental sulfur is produced as a byproduct of removing sulfur-containing contaminants from natural gas and petroleum.. Downloahere Th ...
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Isopropanol
Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, and chloroform, demonstrating its ability to dissolve a wide range of substances including ethyl cellulose, polyvinyl butyral, oils, alkaloids, and natural resins. Notably, it is not miscible with salt solutions and can be separated by adding sodium chloride in a process known as salting out. It forms an azeotrope with water, resulting in a boiling point of 80.37 °C and is characterized by its slightly bitter taste. Isopropyl alcohol becomes viscous at lower temperatures, freezing at −89.5 °C, and has significant ultraviolet-visible absorbance at 205 nm. Chemically, it can be oxidized to acetone or undergo various reactions to form compounds like isopropoxides or aluminium isopropoxide. As an isopropyl group linked ...
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Ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the pseudoelement symbol for ethyl group, ethyl. Ethanol is a Volatility (chemistry), volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. As a psychoactive depressant, it is the active ingredient in alcoholic beverages, and the second most consumed drug globally behind caffeine. Ethanol is naturally produced by the fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration. Historically it was used as a general anesthetic, and has modern medical applications as an antiseptic, disinfectant, solvent for some medications, and antidote for methanol poisoning and ethylene glycol poisoning. It is used as a chemical solvent and in the Chemical synthesis, synthesis of orga ...
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Recrystallization (chemistry)
Recrystallization is a broad class of List of purification methods in chemistry , chemical purification techniques characterized by the dissolution of an impure sample in a solvent or solvent mixture, followed by some change in conditions that encourages the formation of pure isolate as solid crystals. Recrystallization as a purification technique is driven by spontaneous process , spontaneous processes of molecular self-assembly , self-assembly that leverage the highly ordered (i.e. low-entropy) and periodic characteristics of a crystal's molecular structure to produce purification. Basic principles The driving force of this purification emerges from the difference in molecular interactions between the isolate and the impurities: if a molecule of the desired isolate interacts with any isolate crystal present, it is likely the molecule Deposition (chemistry) , deposits on the crystal's ordered surface and contributes to the crystal's growth; if a molecule of the impurity inter ...
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Triphenylphosphine Oxide
Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula , also written as or (Ph = ). It is one of the more common phosphine oxides. This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine. It is a popular reagent to induce the crystallizing of chemical compounds. Structure and properties is structurally related to . As established by X-ray crystallography, the geometry around P is tetrahedral, and the P-O distance is 1.48 Å. Other modifications of have been found: For example, a monoclinic form crystalizes in the space group ''P''21/''c'' with Z = 4 and a = 15.066(1) Å, b = 9.037(2) Å, c = 11.296(3) Å, and β = 98.47(1)°.The orthorhombic modification crystallizes in the space group ''Pbca'' with Z = 4 and 29.089(3) Å, b = 9.1347(9), c = 11.261(1) Å. The oxygen center is relatively basic. The rigidity of the backbone and the basicity of the oxygen ce ...
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Chlorobenzene
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses The major use of chlorobenzene is as a precursor for further intermediates such as nitrophenols, nitroanisole, chloroaniline, and phenylenediamines, which are used in the production of herbicides, dyestuffs, chemicals for rubber, and pharmaceuticals. It is also used as a high-boiling solvent in industrial and laboratory applications, for materials such as oils, waxes, resins, and rubber. Chlorobenzene is nitrated on a large scale to give a mixture of 2-nitrochlorobenzene and 4-nitrochlorobenzene, which are separated and used as intermediates in production of other chemicals. These mononitrochlorobenzenes are converted to related 2-nitrophenol, 2-nitroanis ...
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Phenyllithium
Phenyllithium is an organometallic agent with the empirical formula . It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute. Preparation Phenyllithium was first produced by the reaction of lithium metal with diphenylmercury: : Reaction of a phenyl halide with lithium metal produces phenyllithium: : Phenyllithium can also be synthesized with a metal-halogen exchange reaction: : The predominant method of producing phenyllithium today are the latter two syntheses. Reactions The primary use of PhLi is to facilitate formation of carbon-carbon bonds by nucleophilic addition and substitution reactions: : 2-Phenylpyridine is prepared by the reaction of phenyl lithium with pyridine, a process that entail ...
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Phenylmagnesium Bromide
Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It forms colorless crystals. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph−" synthon. Preparation Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. Laboratory preparation involves treating bromobenzene with magnesium metal, usually in the form of turnings. A small amount of iodine may be used to activate the magnesium to initiate the reaction. Coordinating solvents such as ether or THF, are required to solvate (complex) the magnesium(II) center. The solvent must be aprotic since alcohols and water contain an acidic proton and thus react with phenylmagnesium bromide to give benzene. Carbonyl-containing solvents, such as acetone and ethyl acetate, are also incompatible with the reagent. ...
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Phosphorus Trichloride
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride. History Phosphorus trichloride was first prepared in 1808 by the French chemists Joseph Louis Gay-Lussac and Louis Jacques Thénard by heating calomel (Hg2Cl2) with phosphorus. Later during the same year, the English chemist Humphry Davy produced phosphorus trichloride by burning phosphorus in chlorine gas. Preparation World production exceeds one-third of a million tonnes. Phosphorus trichloride is prepared industrially by the reaction of chlorine with white phosphorus, using phosphorus trichloride as the solvent. In this continuous process PCl3 is removed as it is formed in order to avoid the formation of PCl5. :P4 + 6 Cl2 → 4 PCl3 Structure and spectroscopy It has a t ...
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Diethyl Ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of organic compounds. It is a common solvent and was formerly used as a general anesthetic. Production Most diethyl ether is produced as a byproduct of the vapor-phase Hydration reaction, hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid Catalysis, catalysts and can be adjusted to make more ether if the need arises: Vapor-phase Dehydration reaction, dehydration of ethanol over some Aluminium oxide, alumina catalysts can give diethyl ether yields of up to 95%. : Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Uses The dominant use of diethyl ether is as a solvent. One particular application is in the production of cell ...
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