1,2-Bis(dimethylphosphino)ethane

1,2-Bis(dimethylphosphino)ethane
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Names
	Preferred IUPAC name (Ethane-1,2-diyl)bis(dimethylphosphane)
	Other names DMPE; ethylenebis(dimethylphosphine); 1,2-Bis(dimethylphosphino)ethane
Identifiers
CAS Number	23936-60-9 Y;
3D model (JSmol)	Interactive image;
ChemSpider	124423 Y;
ECHA InfoCard	100.155.809
EC Number	627-450-6;
PubChem CID	141059;
UNII	9P3522CZ8T Y;
CompTox Dashboard (EPA)	DTXSID70178649 ;
	InChI InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Y Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N Y; 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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H250, H315, H319, H335
Precautionary statements	P210, P222, P231, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P335+P334, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) 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, dmpe 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). source ↗

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

Bis(dicyclohexylphosphino)ethane, a bulkier analogue, which is also a solid.
1,2-Bis(diphenylphosphino)ethane, more air-stable than dmpe, but less basic.
1,2-Bis(dimethylphosphino)benzene, a more rigid analogue of dmpe.
Tetramethylethylenediamine, the diamine analogue of dmpe.

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. doi:10.1016/C2009-0-30414-6. 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". Journal of Organometallic Chemistry. 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. Vol. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.

[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. doi:10.1016/C2009-0-30414-6. 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". Journal of Organometallic Chemistry. 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. Vol. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.

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