# Dimethylphosphine

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**Dimethylphosphine** is the [organophosphorus compound](/source/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](/source/Phosphine), a more practical synthesis involves the reduction of tetramethyldiphosphine disulfide with [tributylphosphine](/source/Tributylphosphine):[1]

- (CH3)2P(S)\sP(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](/source/Phosphine), i.e., a compound of the type R2PH. It can be oxidized to the [phosphinic acid](/source/Phosphinic_acid#Organophosphinic_acids):

- (CH3)2PH + O2 → (CH3)2P(O)(OH)

It can be [protonated](/source/Protonated) to give the dimethyl[phosphonium](/source/Phosphonium) ion:

- (CH3)2PH + H+ → [(CH3)2PH2]+

With strong [bases](/source/Bases_(chemistry)) (e.g., [lithium amide](/source/Lithium_amide), it can be deprotonated to give dimethyl [phosphide](/source/Phosphide) derivatives (e.g., lithium dimethyl phosphide):

- (CH3)2PH + LiNH2 → (CH3)2PLi + [NH3](/source/Ammonia)

## References

1. A. Trenkle, H. Vahrenkamp, John Svoboda, Leo Brewer “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. [doi:10.1002/9780470132524.ch40](https://doi.org/10.1002/9780470132524.ch40)

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