Methyldiphenylphosphine


Methyldiphenylphosphine is the organophosphine with the formula CH3(C6H5)2P, often abbreviated PMePh2. It is a colorless, viscous liquid. It is a member of series (CH3)3-n(C6H5)2P that also includes n = 0, n = 1, and n = 3 that are often employed as ligands in metal phosphine complexes.

Methyldiphenylphosphine
Names
Other names
  • Diphenylmethylphosphine
  • Methyldiphenylphosphane
Identifiers
3D model (JSmol)
743075
ChemSpider
ECHA InfoCard 100.014.605
EC Number
  • 216-065-5
UNII
  • InChI=1S/C13H13P/c1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3
    Key: UJNZOIKQAUQOCN-UHFFFAOYSA-N
  • CP(C1=CC=CC=C1)C2=CC=CC=C2
Properties
C13H13P
Molar mass 200.221 g·mol−1
Appearance colorless liquid
Density 1.0779
Melting point 117–118 °C (243–244 °F; 390–391 K)
Boiling point 284 °C (543 °F; 557 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds
 Phenyldimethylphosphine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methyldiphenylphosphine is prepared by reaction of chlorodiphenylphosphine with methyl Grignard reagent:

Cl(C6H5)2P + CH3MgBr → CH3(C6H5)2P + MgBrCl

Selected derivatives:

  • The phosphine oxide OPMePh2, prepared by treatment with hydrogen peroxide.[1]
  • The coordination complex MoH4(PMePh2)4, prepared by treatment of MoCl4(PMePh2)2 with sodium borohydride in the presence of excess ligand.[2]
  • The coordination complex CoCl2(PMePh2)2, prepared by treating cobalt(II) chloride with the phosphine.[3]
  • The phosphine-borane H3BPMePh2 prepared by treating the phosphine with borane.[4]

References
  1. Denniston, Michael L.; Martin, Donald R. (1977). Methyldiphenylphosphine Oxide and Dimethylphenylphosphine Oxide. Inorganic Syntheses. Vol. 17. pp. 183–185. doi:10.1002/9780470132487.ch50. ISBN 9780470132487.
  2. Pennella, Filippo (1974). "Tetrahydridotetrakis(methyldiphenylphosphine)molybdenum(IV)". Inorganic Syntheses. Inorganic Syntheses. Vol. 15. pp. 42–44. doi:10.1002/9780470132463.ch12. ISBN 9780470132463.
  3. Dolcetti, G.; Ghedim, M.; Reed, C. A. (1976). "Bis(Methyldiphenylphosphine)Dichloro-Nitrosylcobalt". Inorganic Syntheses. Inorganic Syntheses. Vol. 16. pp. 29–32. doi:10.1002/9780470132470.ch8. ISBN 9780470132470.
  4. Mathur, M. A.; Myers, W. H.; Sisler, H. H.; Ryschkewitsch, G. E. (1974). "Methyldiphenylphosphine-Borane and Dimethylphenylphosphine-Borane". Inorganic Syntheses. Inorganic Syntheses. Vol. 15. pp. 128–133. doi:10.1002/9780470132463.ch29. ISBN 9780470132463.
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