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==Synthesis==
==Synthesis==
It is synthesised by the reaction of [[methylmagnesium iodide]] with 1,2-bis(dichlorophosphino)ethane:<ref>{{cite journal |author=R. J. Burt, J. Chatt, W. Hussain, 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|J. Organomet. Chem.]] |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}</ref>
It is synthesised by the reaction of [[methylmagnesium iodide]] with 1,2-bis(dichlorophosphino)ethane:<ref>{{cite journal |authors =R. J. Burt, J. Chatt, W. Hussain, 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|J. Organomet. Chem.]] |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}</ref>
:Cl<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PCl<sub>2</sub> + 4 MeMgI → Me<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PMe<sub>2</sub> + 4 MgICl
:Cl<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PCl<sub>2</sub> + 4 MeMgI → Me<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PMe<sub>2</sub> + 4 MgICl
Alternatively but it can be generated by alkylation of sodium dimethylphosphide.
Alternatively but it can be generated by alkylation of sodium dimethylphosphide.

Revision as of 03:31, 14 May 2016

1,2-Bis(dimethylphosphino)ethane
Names
IUPAC name
Ethane-1,2-diylbis(dimethylphosphane)
Other names
DMPE
ethylenebis(dimethylphosphine)
1,2-Bis(dimethylphosphino)ethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.809 Edit this at Wikidata
  • InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 checkY
    Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N checkY
  • InChI=1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
    Key: ZKWQSBFSGZJNFP-UHFFFAOYAN
  • P(C)(C)CCP(C)C
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 labelling:
GHS02: FlammableGHS07: Exclamation mark[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 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]

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

  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 978-0-08-037941-8.
  3. ^ "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. 1979. doi:10.1016/S0022-328X(00)94383-3. {{cite journal}}: Unknown parameter |authors= ignored (help)
  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
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