Misplaced Pages

Dimethylphosphine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Dimethylphosphine
Names
Preferred IUPAC name Dimethylphosphane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H7P/c1-3-2/h3H,1-2H3Key: YOTZYFSGUCFUKA-UHFFFAOYSA-N
SMILES
  • CPC
Properties
Chemical formula (CH3)2PH
Molar mass 62.052 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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 “Dimethylphosphine” Inorganic Syntheses 1982, volume 21, p. 180. doi:10.1002/9780470132524.ch40
Categories: