1,2-Bis(dimethylphosphino)ethane
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477203110
|Name = 1,2-Bis(dimethylphosphino)ethane
|ImageFile = dmpe-2D-skeletal-B.png
|ImageFile1 = Dmpe-from-xtal-1997-3D-balls.png
|PIN = (Ethane-1,2-diyl)bis(dimethylphosphane)
|OtherNames = DMPE
ethylenebis(dimethylphosphine)
1,2-Bis(dimethylphosphino)ethane
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 124423
| EC_number = 627-450-6
|InChI = 1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
|SMILES = P(C)(C)CCP(C)C
|InChIKey = ZKWQSBFSGZJNFP-UHFFFAOYAN
|PubChem = 141059
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = ZKWQSBFSGZJNFP-UHFFFAOYSA-N
|CASNo = 23936-60-9
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 9P3522CZ8T
}}
|Section2={{Chembox Properties
|C=6|H=16|P=2
|BoilingPtC = 180
|BoilingPt_notes =
|Density = 0.9 g/mL at 25 °C
}}
|Section7={{Chembox Hazards
|GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|250|315|319|335}}
| PPhrases = {{P-phrases|210|222|231|233|240|241|242|243|261|264|264+265|271|280|302+335+334|302+352|303+361+353|304+340|305+351+338|319|321|332+317|337+317|362+364|370+378|403+233|403+235|405|501}}
| GHS_ref={{Sigma-Aldrich|Aldrich| id=261939 |name=1,2-Bis(dimethylphosphino)ethane|accessdate=2013-07-20}}
}}
}}
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 (CH{{sub|2}}PMe{{sub|2}}){{sub|2}}, dmpe is used as a compact strongly basic spectator ligand (Me = methyl), Representative complexes include V(dmpe){{sub|2}}(BH{{sub|4}}){{sub|2}}, Mn(dmpe){{sub|2}}(AlH{{sub|4}}){{sub|2}}, Tc(dmpe){{sub|2}}(CO){{sub|2}}Cl, and Ni(dmpe)Cl{{sub|2}}.{{Greenwood&Earnshaw2nd}}
Synthesis
It is synthesised by the reaction of methylmagnesium iodide with 1,2-bis(dichlorophosphino)ethane:{{cite journal |author =R. J. Burt |author2 =J. Chatt |author3 =W. Hussain|author4 =G. J. Leigh |title=A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane |journal=Journal of Organometallic Chemistry |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}
:Cl{{sub|2}}PCH{{sub|2}}CH{{sub|2}}PCl{{sub|2}} + 4 MeMgI → Me{{sub|2}}PCH{{sub|2}}CH{{sub|2}}PMe{{sub|2}} + 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.{{cite book|doi=10.1002/9780470132548.ch42|chapter=Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)|pages=199–200|year=1985|volume=23|last1=Bercaw|first1=J. E.|title=Inorganic Syntheses|last2=Parshall|first2=G. W.|isbn=9780470132548}}
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
{{reflist}}
{{DEFAULTSORT:Bis(dimethylphosphino)ethane, 1, 2-}}