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Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C 6 H 5) 3, also written as Ph 3 PO or PPh 3 O (Ph = C 6 H 5). 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.
Triphenylphosphine undergoes slow oxidation by air to give triphenylphosphine oxide, Ph 3 PO: 2 PPh 3 + O 2 → 2 OPPh 3. This impurity can be removed by recrystallisation of PPh 3 from either hot ethanol or isopropanol. [8] This method capitalizes on the fact that OPPh 3 is more polar and hence more soluble in polar solvents than PPh 3.
The hydrolysis of phosphorus(V) dihalides also affords the oxide: [9] R 3 PCl 2 + H 2 O → R 3 PO + 2 HCl. A special nonoxidative route is applicable secondary phosphine oxides, which arise by the hydrolysis of the chlorophosphine. An example is the hydrolysis of chlorodiphenylphosphine to give diphenylphosphine oxide: Ph 2 PCl + H 2 O → Ph ...
The structure of the phosphine oxide is not strongly perturbed by coordination. The geometry at phosphorus remains tetrahedral. The P-O distance elongates by ca. 2%. In triphenylphosphine oxide, the P-O distance is 1.48 Å. [3] In NiCl 2 [OP(C 6 H 5) 3] 2, the distance is 1.51 Å (see figure).
Boiling point (°C) K b (°C⋅kg/mol) Freezing point (°C) K f (°C⋅kg/mol) Data source; Aniline: 184.3 3.69 –5.96 –5.87 K b & K f [1] Lauric acid:
Melting point: 7.20 °C (44.96 °F; 280.35 K) Boiling point: 232.5 °C (450.5 °F; 505.6 K) CRC [5] ... (such as triphenylphosphine oxide), ...
Triphenylphosphine sulfide (IUPAC name: triphenyl-λ 5-phosphanethione) is the organophosphorus compound with the formula (C 6 H 5) 3 PS, usually written Ph 3 PS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents. Structurally, the molecule resembles the corresponding oxide, with idealized C 3 point ...
Phosphine oxide is the inorganic compound with the formula H 3 PO. Although stable as a dilute gas, liquid or solid samples are unstable. Unlike many other compounds of the type PO x H y, H 3 PO is rarely discussed and is not even mentioned in major sources on main group chemistry.