Dimethylphosphine

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]

[Me2P(S)]2 + PBu3 + H2O → Me2PH + SPBu3 + Me2P(O)H
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
C2H7P
Molar mass 62.05
Appearance colorless gas
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).
Infobox references

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:

Me2PH + O2 → Me2PO2H

It protonates to give the phosphonium ion:

Me2PH + H+ → Me2PH2+

With strong bases, it can be deprotonated to give dimethylphosphide derivatives:

Me2PH + LiNH2 → Me2PLi + NH3

References

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