French
DeutschPyrophosphoryl chloride
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| Names | |
|---|---|
| Other names Diphosphoryl tetrachloride | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.033.462 |
| EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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| Properties | |
| O(POCl2)2 | |
| Molar mass | 251.74 g·mol−1 |
| Appearance | colorless liquid |
| Density | 1.74 g/cm3 |
| Boiling point | 66–68 °C (151–154 °F; 339–341 K) 0.01 Torr |
| Hazards | |
| GHS labelling:[1] | |
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| Danger | |
| H314 | |
| P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Pyrophosphoryl chloride is the inorganic compound with the formula P2O3Cl4. Its structure is O(POCl2)2. It is a colorless syrup. In terms of its chemical structure, the compound consists of two tetrahedral phosphorus sites that share an oxo bridge. The name implies that the compound is a derivative of pyrophosphoric acid, O(PO(OH)2)2.
The compound is obtained by treating phosphoryl chloride with half an equivalent of methanol, as described in the following chemical equation:[1]
Pyrophosphoryl chloride is proposed as an intermediate in the chlorination of alcohols by phosphoryl chloride. It is also a reagent for Vilsmeier-Haack formylations.[2]
References
[edit]- ^ Cheung, Gi K.; Downie, Ian M.; Earle, Martyn J.; Heaney, Harry; Matough, M. Fathy S.; Shuhaibar, Khamis F.; Thomas, Deborah (1992). "A Convenient Preparation of Pyrophosphoryl Chloride and Its Use in Vilsmeier Formylation Reactions". Synlett (1). doi:10.1055/s-1992-21272.
- ^ Downie, Ian M.; Earle, Martyn J.; Heaney, Harry; Shuhaibar, Khamis F. (1993). "Vilsmeier formylation and glyoxylation reactions of nucleophilic aromatic compounds using pyrophosphoryl chloride". Tetrahedron. 49 (19). doi:10.1016/s0040-4020(01)89915-4.