Dimethylphosphine is the

organophosphorus compound Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...

with the formula , often written . It is a malodorous gas that condenses to a colorless liquid just below room temperature. Although it can be produced by methylation of

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

, a more practical synthesis involves the reduction of tetramethyldiphosphine disulfide with

tributylphosphine Tributylphosphine is the organophosphorus compound with the chemical formula , often abbreviated as . It is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rap ...

:A. Trenkle, H. Vahrenkamp “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. :

Reactions

The compound exhibits the properties characteristic of a secondary

, i.e., a compound of the type . It can be oxidized to the phosphinic acid: : It can be protonated to give the dimethyl

phosphonium In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, organyl or halogen group). These cations have tetrahedral structures. The ...

ion: : With strong bases (e.g., lithium amide, it can be deprotonated to give dimethyl

phosphide In chemistry, a phosphide is a compound containing the ion or its equivalent. Many different phosphides are known, with widely differing structures. Most commonly encountered on the binary phosphides, i.e. those materials consisting only of pho ...

derivatives (e.g., lithium dimethyl phosphide): :

References

{{Reflist Phosphines Foul-smelling chemicals