Dimethylphosphine
Dimethylphosphine is the organophosphorus compound with the formula (CH3)2PH, often written Me2PH. It is a malodorous gas that condenses to a colorless liquid just below room temperature. Although it can be produced by methylation of phosphine, a more practical synthesis involves the reduction of tetramethyldiphosphine disulfide with tributylphosphine:[1]
- [Me2P(S)]2 + PBu3 + H2O → Me2PH + SPBu3 + Me2P(O)H
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| Preferred IUPAC name
Dimethylphosphane | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C2H7P | |
| Molar mass | 62.05 |
| Appearance | colorless gas |
| Boiling point | 21.1 °C |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions
The compound exhibits the properties characteristic of a secondary phosphine, i.e., a compound of the type R2PH. It can be oxidized to the phosphinic acid:
- Me2PH + O2 → Me2PO2H
It protonates to give the phosphonium ion:
- Me2PH + H+ → Me2PH2+
With strong bases, it can be deprotonated to give dimethylphosphide derivatives:
- Me2PH + LiNH2 → Me2PLi + NH3
References
- A. Trenkle, H. Vahrenkamp “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. doi:10.1002/9780470132524.ch40
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