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Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula P H 3, 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 (P 2 H 4).
For example, lithium diphenylphosphide is readily methylated with methyl iodide to give methyldiphenylphosphine: LiiP(C 6 H 5) 2 + CH 3 I → CH 3 P(C 6 H 5) 2 + LiI. Phosphine is a precursor to some tertiary phosphines by hydrophosphination of alkenes. For example, in the presence of basic catalysts PH 3 adds of Michael acceptors such as ...
With the formula (HO) 2 P(O)CH 2 NHCH 2 CO 2 H, this derivative of glycine is one of the most widely used herbicides. Bisphosphonates are a class of drugs to treat osteoporosis. The nerve gas agent sarin, containing both C–P and F–P bonds, is a phosphonate. Phosphinates feature two P–C bonds, with the general formula R 2 P(=O)(OR').
General formula of organophosphine oxides. Phosphine oxides are phosphorus compounds with the formula OPX 3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl 3). [1] The parent phosphine oxide (H 3 PO) remains rare and obscure.
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. 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.
One of the first applications of phosphine ligands in catalysis was the use of triphenylphosphine in "Reppe" chemistry (1948), which included reactions of alkynes, carbon monoxide, and alcohols. [16] In his studies, Reppe discovered that this reaction more efficiently produced acrylic esters using NiBr 2 (PPh 3) 2 as a catalyst instead of NiBr 2.
Phosphine (PH 3) and its organic derivatives (PR 3) are structural analogues of ammonia (NH 3), but the bond angles at phosphorus are closer to 90° for phosphine and its organic derivatives. Phosphine is an ill-smelling, toxic gas. Phosphorus has an oxidation number of −3 in phosphine. Phosphine is produced by hydrolysis of calcium phosphide ...
Skeletal formula of a generic diphosphine ligand. R represents a side chain.The phosphine donors are connected by a backbone linker. Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry.