1,2-Bis(dimethylphosphino)ethane

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1,2-Bis(dimethylphosphino)ethane
Dmpe-2D-skeletal-B.png
Dmpe-from-xtal-1997-3D-balls.png
Names
IUPAC name
Ethane-1,2-diylbis(dimethylphosphane)
Other names
DMPE
ethylenebis(dimethylphosphine)
1,2-Bis(dimethylphosphino)ethane
Identifiers
23936-60-9 N
ChemSpider 124423 YesY
Jmol 3D model Interactive image
PubChem 141059
Properties
C6H16P2
Molar mass 150.14 g mol−1
Density 0.9 g/mL at 25 °C
Boiling point 180 °C (356 °F; 453 K)
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[1]
R-phrases H225, H315, H319, H335[1]
S-phrases P210, P261, P305+351+338[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Bis(dimethylphosphino)ethane (dmpe) is a diphosphine ligand in coordination chemistry. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CH2PMe2)2 is used as a compact strongly basic spectator ligand (Me = methyl), Representative complexes include V(dmpe)2(BH4)2, Mn(dmpe)2(AlH4)2, Tc(dmpe)2(CO)2Cl, and Ni(dmpe)Cl2.[2]

Structure of trans-CoCl2(dmpe)2 (P is ochre, Co. is blue, Cl is green.

Synthesis[edit]

It is synthesised by the reaction of methylmagnesium iodide with 1,2-bis(dichlorophosphino)ethane:[3]

Cl2PCH2CH2PCl2 + 4 MeMgI → Me2PCH2CH2PMe2 + 4 MgICl

Alternatively but it can be generated by alkylation of sodium dimethylphosphide.

The synthesis of dmpe from thiophosphoryl chloride has led to serious accidents and has been abandoned.[4]

Related ligands[edit]

Tetramethylethylenediamine is the diamine analogue of dmpe. Bis(dicyclohexylphosphino)ethane is a bulky analogue of dmpe, which offers the advantage of being a solid.

References[edit]

  1. ^ a b c Sigma-Aldrich Co., 1,2-Bis(dimethylphosphino)ethane. Retrieved on 2013-07-20.
  2. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0-08-037941-9. 
  3. ^ R. J. Burt; J. Chatt; W. Hussain; G. J. Leigh (1979). "A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane". J. Organomet. Chem. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3. 
  4. ^ J. E. Bercaw, G. W. Parshall, "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(dimethylphosphine) (dmpe)" Inorganic Syntheses 1985, vol. 23, Pages: 199–200. doi:10.1002/9780470132548.ch42