Dimethylphenylphosphine
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| Names | |||
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IUPAC name
Dimethylphenylphosphane
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| Other names
Dimethylphenylphosphine
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| Identifiers | |||
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3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.010.543 | ||
| EC Number | 211-595-3 | ||
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PubChem CID
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| Properties | |||
| C8H11P | |||
| Molar mass | 138.14 g/mol | ||
| Appearance | transparent light pale yellow liquid | ||
| Density | 0.971 g/cm3 | ||
| Melting point | N/A | ||
| Boiling point | 74 to 75 °C (165 to 167 °F; 347 to 348 K) at 12 mmHg | ||
| Insoluble | |||
| Structure | |||
| Pyramidal | |||
| Hazards | |||
| Safety data sheet | [1] | ||
| R-phrases (outdated) | R10 R36 R37 R38 | ||
| S-phrases (outdated) | S26 S36 | ||
| Flash point | 49 °C (120 °F; 322 K) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Dimethylphenylphosphine is an organophosphorus compound with a formula P(C6H5)(CH3)2. The phosphorus is connected to a phenyl group and two methyl groups, making it the simplest aromatic alkylphosphine. This colorless air sensitive liquid is commonly used as a ligand in transition metal complexes. These complexes are often soluble in organic solvents.
Dimethylphenylphosphine is prepared by the reaction of methylmagnesium halide with dichlorophenylphosphine.
The phosphine is purified by distillation under reduced pressure. A solution of (C6H5)(CH3)2P in CDCl3 shows proton NMR signals at δ 7.0-7.5 and a doublet at δ 1.2. The phosphorus-31 NMR spectrum shows a singlet at -45.9 ppm in CDCl3.
Dimethylphenylphosphine is a pyramidal molecule where the phenyl group and two methyl groups are connected to the phosphorus. The bond length and angles are the following: P-CMe: 1.844, P-CPh: 1.845 Å, C-C: 1.401 Å, C-HMe: 1.090 Å, C-HPh: 1.067 Å, C-P-C: 96.9°, C-P-C (ring): 103.4°, P-C-H: 115.2°.
When attached to chiral metal centers, the P-methyl groups are diastereotopic, appearing as separate doublets in the 1H NMR spectrum.
The νCO of IrCl(CO)(PPh3)2 and IrCl(CO)(PMe2Ph)2 are both at 1960 cm−1, whereas νCO for IrCl(CO)(PMe3)2 is at 1938 cm−1.
In terms of basicity, dimethylphenylphosphine is intermediate between that of trialkyl- and triphenylphosphine:
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