1,2-Bis(dimethylphosphino)ethane: Difference between revisions

1,2-Bis(dimethylphosphino)ethane
Names
	IUPAC name Ethane-1,2-diylbis(dimethylphosphane)
	Other names DMPE; ethylenebis(dimethylphosphine); 1,2-Bis(dimethylphosphino)ethane
Identifiers
CAS Number	23936-60-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	124423 ;
ECHA InfoCard	100.155.809
PubChem CID	141059;
CompTox Dashboard (EPA)	DTXSID70178649 ;
	InChI InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N ; 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	150.14 g mol−1
Density	0.9 g/mL at 25 °C
Boiling point	180 °C (356 °F; 453 K)
Hazards
	GHS labelling:
Pictograms
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 04:13, 16 May 2016

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]

Related ligands

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

^ ^a ^b ^c 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. 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". J. Organomet. Chem. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3.
^ 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

[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. 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". J. Organomet. Chem. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3.

[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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@@ Line 26: / Line 26: @@
 |Section2={{Chembox Properties
 | Formula = C<sub>6</sub>H<sub>16</sub>P<sub>2</sub>
-| MolarMass = 150.14 g&nbsp;mol<sup>−1</sup>
+| MolarMass = 150.14 g mol<sup>−1</sup>
 | BoilingPtC = 180
 | BoilingPt_notes =
@@ Line 47: / Line 47: @@
 '''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</sub>PMe<sub>2</sub>)<sub>2</sub> is used as a compact strongly basic [[spectator ligand]] (Me = [[methyl]]),  Representative complexes include V(dmpe)<sub>2</sub>(BH<sub>4</sub>)<sub>2</sub>, Mn(dmpe)<sub>2</sub>(AlH<sub>4</sub>)<sub>2</sub>, Tc(dmpe)<sub>2</sub>(CO)<sub>2</sub>Cl, and Ni(dmpe)Cl<sub>2</sub>.<ref>{{Greenwood&Earnshaw2nd}}</ref>
-[[File:Trans-CoCl2(dmpe)2.png|thumb|left|Structure of ''trans''-CoCl<sub>2</sub>(dmpe)<sub>2</sub> (P is ochre, Co is blue, Cl is green.<!--CSDZIGFIEtr-->]]
+[[File:Trans-CoCl2(dmpe)2.png|thumb|left|Structure of ''trans''-CoCl<sub>2</sub>(dmpe)<sub>2</sub> (P is ochre, Co. is blue, Cl is green.<!--CSDZIGFIEtr-->]]
 ==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 |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>
 :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.