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Phosphorus-containing Compounds
Organophosphorus compounds are organic compounds that contain phosphorus. However, a compound need not have a direct phosphorus-carbon (P-C) bond for it to be considered an organophosphorus compound; it is sufficient that phosphorus contain only an organic substituent. While phosphorus can exist in oxidation states -3 to +5, organophosphorus compounds are generally classified based on their being derivatives of phosphorus(V) or phosphorus(III), which are the predominant classes of organophosphorus compounds. Examples of organophosphorus (V) compounds are esters of organophosphorus acids (P(=O)(OR) ), phosphonic esters (RP(=O)(OR') ), phosphine oxides (R P=O), phosphites (P(OR) ), organic fluorophosphate salts, organic phosphate salts, organophophorus acid halides, organophosphorus amides, organophosphorus complexes, and organophosphorus halides. Phosphines, phosphaalkenes, phosphaalkynes, phosphites, phosphonites, and phosphinites are examples of organophosphorus (III) compounds.
The Thermo Scientific portfolio includes phosphorus-containing organic compounds suitable for a variety of research and development applications.
Organophosphorus esters are derived derived from the reactions of their corresponding acids with alcohols. Examples of organophosporus esters are phosphonates, RP(=O)(OR)2, which are esters of phosphonic acid; phosphinates, R2P(=O)(OR'), which are the esters of phosphinic acid; phosphonites, P(OR)2R', which are esters of phosphonous acid; and phosphinites, P(OR)R'2, which are esters of phosphinous acid.
Organophosphorus amides are organic compounds containing at least one phosphorous-nitrogen bond. They are also referred to as amides of organophosphorous acids. These compounds are physically more stable in open air and soluble in many organic solvents. Organophosphorus amides have also attracted the development of new molecules with wide-ranging applications. HMPT (hexamethylphosphorous triamide) is useful as a phosphorylating agent in synthetic chemistry and as a flame retardant in building materials. Hexamethylphosphoramide (HPMA) is useful as a specialty solvent and improves selectivity and the rate of reaction.
Phosphines (also referred to as phosphanes) are a class of organophosphorus compounds represented by the formula PR3 (R = hydrogen or alkyl or aryl). They are classified as primary, secondary, and tertiary phosphines and are represented by the formula RPH2, R2PH, and R3P. Examples include triphenylphosphine [(C6H5)3P], tri-n-butylphosphine, and BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl), and triisopropylphosphine. Phosphines are used extensively in organophosphorous chemistry primarily as intermediates.
Phosphines are commonly used as ligands to form metal complexes such as Wilkinson's catalyst [Rh(PPh3)3Cl] and Grubbs' catalyst. Phosphine ligands are useful as catalysts in reactions involving alkynes, carbon monoxide, and alcohols. The nucleophilic catalysts used in the dimerization of enones for the Rauhut-Currier reaction are phosphines. Phosphines are also used in the conversion of azides to amines in the Staudinger reduction, and alcohols into esters in the Mitsunobu reaction. The organophosphines form coordination complexes with various metal ions, and therefore they can be used as catalysts in many chemical reactions. Metal complexes with chiral phosphines can be used as catalysts to achieve enantio- or diastereoselectivity.
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