1,2-Bis(dimethylphosphino)ethane

1,2-Bis(dimethylphosphino)ethane
Names
	IUPAC name Ethane-1,2-diylbis(dimethylphosphane)
	Other names DMPE; ethylenebis(dimethylphosphine); 1,2-Bis(dimethylphosphino)ethane
Identifiers
CAS Number	23936-60-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	124423 ;
ECHA InfoCard	100.155.809
PubChem CID	141059;
CompTox Dashboard (EPA)	DTXSID70178649 ;
	InChI InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N ; InChI=1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Key: ZKWQSBFSGZJNFP-UHFFFAOYAN;
	SMILES P(C)(C)CCP(C)C;
Properties
Chemical formula	C6H16P2
Molar mass	150.142 g·mol−1
Density	0.9 g/mL at 25 °C
Boiling point	180 °C (356 °F; 453 K)
Hazards
GHS pictograms	[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

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

Cl₂PCH₂CH₂PCl₂ + 4 MeMgI → Me₂PCH₂CH₂PMe₂ + 4 MgICl

Alternatively 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

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

Sigma-Aldrich Co., 1,2-Bis(dimethylphosphino)ethane. Retrieved on 2013-07-20.
Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
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.
Bercaw, J. E.; Parshall, G. W. (1985). "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)". Inorganic Syntheses. Inorganic Syntheses. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.}

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[sigma-1] 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 978-0-08-037941-8.

[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] Bercaw, J. E.; Parshall, G. W. (1985). "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)". Inorganic Syntheses. Inorganic Syntheses. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.}