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1,2-Bis(dimethylphosphino)ethane

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]

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
  • 23936-60-9 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 124423 Y
ECHA InfoCard 100.155.809
EC Number
  • 627-450-6
  • 141059
UNII
  • 9P3522CZ8T Y
  • DTXSID70178649
  • InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Y
    Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N Y
  • 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]
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 YN ?)
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]

Related ligands 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.}

dimethylphosphino, ethane, dmpe, diphosphine, ligand, coordination, chemistry, colorless, sensitive, liquid, that, soluble, organic, solvents, with, formula, ch2pme2, dmpe, used, compact, strongly, basic, spectator, ligand, methyl, representative, complexes, i. 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 1 2 Bis dimethylphosphino ethane NamesPreferred IUPAC name Ethane 1 2 diyl bis dimethylphosphane Other names DMPEethylenebis dimethylphosphine 1 2 Bis dimethylphosphino ethaneIdentifiersCAS Number 23936 60 9 Y3D model JSmol Interactive imageChemSpider 124423 YECHA InfoCard 100 155 809EC Number 627 450 6PubChem CID 141059UNII 9P3522CZ8T YCompTox Dashboard EPA DTXSID70178649InChI InChI 1S C6H16P2 c1 7 2 5 6 8 3 4 h5 6H2 1 4H3 YKey ZKWQSBFSGZJNFP UHFFFAOYSA N YInChI 1 C6H16P2 c1 7 2 5 6 8 3 4 h5 6H2 1 4H3Key ZKWQSBFSGZJNFP UHFFFAOYANSMILES P C C CCP C CPropertiesChemical formula C 6H 16P 2Molar mass 150 142 g mol 1Density 0 9 g mL at 25 CBoiling point 180 C 356 F 453 K HazardsGHS labelling 1 PictogramsSignal word DangerHazard statements H225 H250 H315 H319 H335Precautionary 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 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Structure of trans CoCl2 dmpe 2 P is ochre Co is blue Cl is green Synthesis editIt is synthesised by the reaction of methylmagnesium iodide with 1 2 bis dichlorophosphino ethane 3 Cl2PCH2CH2PCl2 4 MeMgI Me2PCH2CH2PMe2 4 MgIClAlternatively 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 editBis 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 edit 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 Journal of Organometallic Chemistry 182 2 203 6 doi 10 1016 S0022 328X 00 94383 3 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 Retrieved from https en wikipedia org w index php title 1 2 Bis dimethylphosphino ethane amp oldid 1218401386, wikipedia, wiki, book, books, library,

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