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Those with five organic substituents are rare, although P(C 6 H 5) 5 is known, being derived from P(C 6 H 5) 4 + by reaction with phenyllithium. Phosphorus ylides are unsaturated phosphoranes, known as Wittig reagents, e.g. CH 2 P(C 6 H 5) 3. These compounds feature tetrahedral phosphorus(V) and are considered relatives of phosphine oxides.
The latter is a common feature of the chemistry of phosphorus. As a result, the lone pair of trimethylphosphine has predominantly s-character as is the case for phosphine, PH 3. [10] Tertiary phosphines are pyramidal. When the organic substituents all differ, the phosphine is chiral and
Methylphosphonyl dichloride is produced by oxidation of methyldichlorophosphine, with sulfuryl chloride: [3]. CH 3 PCl 2 + SO 2 Cl 2 → CH 3 P(O)Cl 2 + SOCl 2. It can also be produced from a range of methylphosphonates (e.g. dimethyl methylphosphonate) via chlorination with thionyl chloride.
Organophosphate flame retardants are part of a wider family of phosphorus-based agents which include organic phosphonate and phosphinate esters, in addition to inorganic salts. [ 58 ] [ 59 ] When some prominent brominated flame retardant were banned in the early 2000s phosphorus-based agents were promoted as safer replacements.
The term phosphate is also used in organic chemistry for the functional groups that result when one or more of the hydrogens are replaced by bonds to other groups. These acids, together with their salts and esters , include some of the best-known compounds of phosphorus, of high importance in biochemistry , mineralogy , agriculture , pharmacy ...
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.
The formal oxidation state of phosphorus is +4. The oxygen analogue is the hypodiphosphate anion, P 2 O 4− 6. P 3 S 3− 9 contains a six-membered P 3 S 3 ring. The ammonium salt is produced by reaction of P 4 S 10 in liquid ammonia. [13] Another way of visualising the structure is that it is the P 4 S 10 adamantane (P 4 O 10) structure with ...
Organic sources, namely urine, bone ash and (in the latter 19th century) guano, were historically of importance but had only limited commercial success. [44] As urine contains phosphorus, it has fertilising qualities which are still harnessed today in some countries, including Sweden, using methods for reuse of excreta.