Chemistry:Dimethylphosphine

Dimethylphosphine

Names
Preferred IUPAC name Dimethylphosphane
Identifiers
CAS Number	676-59-5
3D model (JSmol)	Interactive image
ChemSpider	62810
PubChem CID	69607
UNII	DRV85A28TP Y
InChI InChI=1S/C2H7P/c1-3-2/h3H,1-2H3 Key: YOTZYFSGUCFUKA-UHFFFAOYSA-N
SMILES CPC
Properties
Chemical formula	(CH 3) 2PH
Molar mass	62.052 g·mol−1
Appearance	Colorless gas or colorless liquid
Odor	Malodorous
Boiling point	21.1 °C
Hazards
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

Tracking categories (test):

• SizeSet

Dimethylphosphine is the organophosphorus compound with the formula (CH
3)
2PH, often written Me
2PH. 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:

(CH
3)
2P(S)–P(S)(CH
3)
2 + P((CH
2)
3CH
3)
3 + H
2O → (CH
3)
2PH + SP((CH
2)
3CH
3)
3 + (CH
3)
2P(O)(OH)

Reactions

The compound exhibits the properties characteristic of a secondary phosphine, i.e., a compound of the type R
2PH. It can be oxidized to the phosphinic acid:

(CH
3)
2PH + O
2 → (CH
3)
2P(O)(OH)

It can be protonated to give the dimethylphosphonium ion:

(CH
3)
2PH + H+
→ [(CH
3)
2PH
2]+

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

(CH
3)
2PH + LiNH
2 → (CH
3)
2PLi + NH
3