Dimethylphosphine
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Preferred IUPAC name Dimethylphosphane | |
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Properties | |
Chemical formula | (CH3)2PH |
Molar mass | 62.052 g·mol−1 |
Appearance | Colorless gas or colorless liquid |
Odor | Malodorous |
Boiling point | 21.1 °C |
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Main hazards | toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
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
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
- ^ A. Trenkle, H. Vahrenkamp “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. doi:10.1002/9780470132524.ch40