Dimethylphosphine

Dimethylphosphine
Names
Preferred IUPAC name
Dimethylphosphane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C2H7P/c1-3-2/h3H,1-2H3
    Key: YOTZYFSGUCFUKA-UHFFFAOYSA-N
  • CPC
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).

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:

(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

  1. ↑ A. Trenkle, H. Vahrenkamp, John Svoboda, Leo Brewer “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. doi:10.1002/9780470132524.ch40