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==Synthesis==
==Synthesis==
It is synthesised by the reaction of [[methylmagnesium iodide]] with [[1,2-Bis(dichlorophosphino)ethane|1,2-bis(dichlorophosphino)ethane]]:<ref>{{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|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|1,2-bis(dichlorophosphino)ethane]]:<ref>{{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}}</ref>
: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
: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.
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.<ref>{{cite book|doi=10.1002/9780470132548.ch42|chapter=Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)|series=Inorganic Syntheses|pages=199–200|year=1985|volume=23|last1=Bercaw|first1=J. E.|title=Inorganic Syntheses|last2=Parshall|first2=G. W.|isbn=9780470132548}}}</ref>
The synthesis of dmpe from [[thiophosphoryl chloride]] has led to serious accidents and has been abandoned.<ref>{{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}}</ref>


==Related ligands==
==Related ligands==

Latest revision as of 12:43, 12 December 2024

1,2-Bis(dimethylphosphino)ethane
Names
Preferred IUPAC name
(Ethane-1,2-diyl)bis(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
EC Number
  • 627-450-6
UNII
  • 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 150.142 g·mol−1
Density 0.9 g/mL at 25 °C
Boiling point 180 °C (356 °F; 453 K)
Hazards
GHS labelling:[1]
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H250, H315, H319, H335
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 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, 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).

Synthesis

[edit]

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]

[edit]

References

[edit]
  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". 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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