Methyldiphenylphosphine

Methyldiphenylphosphine
Names
	Other names Diphenylmethylphosphine; Methyldiphenylphosphane;
Identifiers
CAS Number	1486-28-8;
3D model (JSmol)	Interactive image;
Beilstein Reference	743075
ChemSpider	66513;
ECHA InfoCard	100.014.605
EC Number	216-065-5;
PubChem CID	73879;
UNII	RYN4FS3JEN;
CompTox Dashboard (EPA)	DTXSID30164028;
	InChI 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;
	SMILES CP(C1=CC=CC=C1)C2=CC=CC=C2;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	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 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 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

^ 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.
^ Pennella, Filippo (1974). "Tetrahydridotetrakis(methyldiphenylphosphine)molybdenum(IV)". Inorganic Syntheses. Inorganic Syntheses. Vol. 15. pp. 42–44. doi:10.1002/9780470132463.ch12. ISBN 9780470132463.
^ 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.
^ 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.

[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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