Dimethylphosphine
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| Names | |
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| Preferred IUPAC name
Dimethylphosphane | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| (CH3)2PH | |
| Molar mass | 62.052 g·mol−1 |
| Appearance | Colorless gas or colorless liquid |
| Odor | Malodorous |
| 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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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]
- (CH3)2P(S)−P(S)(CH3)2 + P((CH2)3CH3)3 + H2O → (CH3)2PH + SP((CH2)3CH3)3 + (CH3)2P(O)(OH)
Reactions
[edit]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:
- (CH3)2PH + O2 → (CH3)2P(O)(OH)
It can be protonated to give the dimethylphosphonium ion:
- (CH3)2PH + H+ → [(CH3)2PH2]+
With strong bases (e.g., lithium amide, it can be deprotonated to give dimethyl phosphide derivatives (e.g., lithium dimethyl phosphide):
- (CH3)2PH + LiNH2 → (CH3)2PLi + NH3
References
[edit]- ↑ A. Trenkle, H. Vahrenkamp, John Svoboda, Leo Brewer “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. doi:10.1002/9780470132524.ch40