Misplaced Pages

1,2-Bis(dimethylphosphino)ethane

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is the current revision of this page, as edited by Rjwilmsi (talk | contribs) at 12:43, 12 December 2024 (→Synthesis: brackets in ref fix). The present address (URL) is a permanent link to this version.

Revision as of 12:43, 12 December 2024 by Rjwilmsi (talk | contribs) (→Synthesis: brackets in ref fix)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.809 Edit this at Wikidata
EC Number
  • 627-450-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N
  • InChI=1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3Key: ZKWQSBFSGZJNFP-UHFFFAOYAN
SMILES
  • P(C)(C)CCP(C)C
Properties
Chemical formula C6H16P2
Molar mass 150.142 g·mol
Density 0.9 g/mL at 25 °C
Boiling point 180 °C (356 °F; 453 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Danger
Hazard statements H225, H250, H315, H319, H335
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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:

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.

Related ligands

References

  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.
Categories: