1,2-Bis(dimethylphosphino)ethane (dmpe) is a

diphosphine ligand Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligand, phosphine ligands in inorganic chemistry, inorganic and organometallic chemistry. They are identified by the presence of ...

coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CHPMe), dmpe is used as a compact strongly basic

spectator ligand In coordination chemistry, a spectator ligand is a ligand that does not participate in chemical reactions of the complex. Instead, spectator ligands (vs "actor ligands") occupy coordination sites. Spectator ligands tend to be of polydentate, such ...

(Me =

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

), Representative complexes include V(dmpe)(BH), Mn(dmpe)(AlH), Tc(dmpe)(CO)Cl, and Ni(dmpe)Cl. Trans-CoCl2(dmpe)2

Synthesis

It is synthesised by the reaction of

methylmagnesium iodide Methylmagnesium chloride is an organometallic compound with the general formula CH3MgCl. This highly flammable, colorless, and moisture sensitive material is the simplest Grignard reagent and is commercially available, usually as a solution in tet ...

with 1,2-bis(dichlorophosphino)ethane: :ClPCHCHPCl + 4 MeMgI → MePCHCHPMe + 4 MgICl Alternatively it can be generated by alkylation of sodium dimethylphosphide. The synthesis of dmpe from

thiophosphoryl chloride Thiophosphoryl chloride is an inorganic compound with the formula PSCl3.Spilling, C. D. "Thiophosphoryl Chloride" in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, Weinheim, 2001. . Article Online Posting Date: April 15, 2001. ...

has led to serious accidents and has been abandoned.}

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 Onekama ( ) is a village in Manistee County, Michigan, Manistee County in the U.S. state of Michigan. The population was 411 at the 2010 United States Census, 2010 census. The village is located on the shores of Portage Lake (Michigan), Portage Lak ...

, a more rigid analogue of dmpe. *

Tetramethylethylenediamine Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four amine hydrogens with four methyl groups. It is a colorless liquid ...

, the diamine analogue of dmpe.

References

{{DEFAULTSORT:Bis(dimethylphosphino)ethane, 1, 2- Chelating agents Diphosphines 1,2-Ethanediyl compounds