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Dimethylphosphine
Dimethylphosphine is the organophosphorus compound with the formula (CH3)2PH, often written Me2PH. It is a malodorous gas that condenses to a colorless liquid just below room temperature. Although it can be produced by methylation of phosphine, a more practical synthesis involves the reduction of tetramethyldiphosphine disulfide with tributylphosphine:A. Trenkle, H. Vahrenkamp “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. : e2P(S)sub>2 + PBu3 + H2O → Me2PH + SPBu3 + Me2P(O)H Reactions The compound exhibits the properties characteristic of a secondary phosphine, i.e., a compound of the type R2PH. It can be oxidized to the phosphinic acid: :Me2PH + O2 → Me2PO2H It protonates to give the phosphonium ion: :Me2PH + H+ → Me2PH2+ With strong bases, it can be deprotonated to give dimethylphosphide In chemistry, a phosphide is a compound containing the ion or its equivalent. Many different phosphides are known, with widely differin ...
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Organophosphorus Compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt ...
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Phosphine
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane (). With traces of present, is spontaneously flammable in air ( pyrophoric), burning with a luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure. Phosphines are compounds that include and the organophosphines, which are derived from by substituting one or more hydrogen atoms with organic groups. They have the general formula . Phosphanes are saturated phosphorus hydrides of the form , such as triphosphane. Phosphine, PH3, is the smallest of the phosphines and the smallest of the phosphanes. History Philippe Gengembre (1764–1838), a student of Lavois ...
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Tributylphosphine
Tributylphosphine is the organophosphorus compound with the formula P(CH). Abbreviated or PBu, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques. Preparation Tributylphosphine is prepared industrially by the hydrophosphination of phosphine with butene: the addition proceeds by a free radical mechanism, and so the Markovnikov rule is not followed. :PH + 3CH=CHCHCH → P(CHCHCHCH) Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation. :3 BuMgCl + PCl → PBu + 3 MgCl Reactions Tributylphosphine reacts with oxygen to give the phosphine oxide: :2 PBu3 + O2 → 2 OPBu3 Because ...
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Phosphinic Acid
Hypophosphorous acid (HPA), or phosphinic acid, is a phosphorus oxyacid and a powerful reducing agent with molecular formula H3PO2. It is a colorless low-melting compound, which is soluble in water, dioxane and alcohols. The formula for this acid is generally written H3PO2, but a more descriptive presentation is HOP(O)H2, which highlights its monoprotic character. Salts derived from this acid are called hypophosphites. HOP(O)H2 exists in equilibrium with the minor tautomer HP(OH)2. Sometimes the minor tautomer is called hypophosphorous acid and the major tautomer is called phosphinic acid. Preparation and availability Hypophosphorous acid was first prepared in 1816 by the French chemist Pierre Louis Dulong (1785–1838). The acid is prepared industrially via a two step process: Firstly, elemental white phosphorus reacts with alkali and alkaline earth hydroxides to give an aqueous solution of hypophosphites: :P4 + 4 OH− + 4 H2O → 4  + 2 H2 Any phosph ...
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Phosphonium
In polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions. Types of phosphonium cations Protonated phosphines The parent phosphonium is as found in the iodide salt, phosphonium iodide. Salts of the parent are rarely encountered, but this ion is an intermediate in the preparation of the industrially useful tetrakis(hydroxymethyl)phosphonium chloride: :PH3 + HCl + 4 CH2O → Many organophosphonium salts are produced by protonation of primary, secondary, and tertiary phosphines: :PR3 + H+ → The basicity of phosphines follows the usual trends, with R = alkyl being more basic than R = aryl. Tetraorganophosphonium cations The most common phosphonium compounds have four organic substituents attached to phosphorus. The quaternary phosphonium cations include tetraphenylphosphonium, (C6H5)4P+ and tetramethylphosphoni ...
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Phosphide
In chemistry, a phosphide is a compound containing the ion or its equivalent. Many different phosphides are known, with widely differing structures. Most commonly encountered on the binary phosphides, i.e. those materials consisting only of phosphorus and a less electronegative element. Numerous are polyphosphides, which are solids consisting of anionic chains or clusters of phosphorus. Phosphides are known with the majority of less electronegative elements with the exception of Hg, Pb, Sb, Bi, Te, and Po.Von Schnering, H.G. and Hönle , W. (1994) "Phosphides - Solid-state Chemistry" in ''Encyclopedia of Inorganic Chemistry''. R. Bruce King (ed.). John Wiley & Sons Finally, some phosphides are molecular. Binary phosphides Binary phosphides include phosphorus and one other element. An example of a group 1 phosphide is sodium phosphide (). Other notable examples include aluminium phosphide () and calcium phosphide (), which are used as pesticides, exploiting their tendenc ...
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Phosphines
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane (). With traces of present, is spontaneously flammable in air (pyrophoric), burning with a luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure. Phosphines are compounds that include and the organophosphines, which are derived from by substituting one or more hydrogen atoms with organic groups. They have the general formula . Phosphanes are saturated phosphorus hydrides of the form , such as triphosphane. Phosphine, PH3, is the smallest of the phosphines and the smallest of the phosphanes. History Philippe Gengembre (1764–1838), a student of Lavoisier, f ...
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