(2-Bromophenyl)diphenylphosphine
 | |
| Names | |
|---|---|
| Other names
(o-Bromophenyl)diphenylphosphine, (2-Bromophenyl)diphenylphosphane | |
| Identifiers | |
| 62336-24-7 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 101130 |
| EC Number | 263-515-1 |
| PubChem | 112836 |
| |
| |
| Properties | |
| C18H14BrP | |
| Molar mass | 341.18 |
| Appearance | white solid |
| Melting point | 115 °C |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
(2-Bromophenyl)diphenylphosphine is an organophosphorus compound with the formula (C6H4Br)P(C6H5)2. It is a white crystalline solid that is soluble in nonpolar organic solvents. The compound is used as a precursor to the 2-lithiated derivative of triphenylphosphine,[1] which in turn is a precursor to other phosphine ligands.
Preparation
The compound has been prepared by several methods.[1] An efficient route is the coupling reaction of diphenylphosphine and 2-bromoiodobenzne, which is catalyzed by palladium complexes (Ph = C6H5):[2]
- C6H4Br(I) + HPPh2 + Et3N → Ph2P(C6H4Br) + [Et3NH]I
The compound is isomorphous with (2-tolyl)diphenylphosphine.[3]
References
- 1 2 Bennett, M. A.; Bhargava, S. K.; Hockless, D. C. R.; Welling, L. L.; Willis, A. C., "Dinuclear Cycloaurated Complexes Containing Bridging (2-Diphenylphosphino)phenylphosphine and (2-Diethylphosphino)phenylphosphine, C6H4PR2 (R = Ph, Et). Carbon−Carbon Bond Formation by Reductive Elimination at a Gold(II)−Gold(II) Center", Journal of the American Chemical Society 1996, volume 118, 10469-10478. doi:10.1021/ja961511h
- ↑ Zhang, F.; Wang, L.; Chang, S.-H.; Huang, K.-L.; Chi, Y.; Hung, W.-Y.; Chen, C.-M.; Lee, G.-H.; Chou, P.-T., "Phosphorescent Ir(iii) complexes with both cyclometalate chromophores and phosphine-silanolate ancillary: concurrent conversion of organosilane to silanolate", Dalton Trans. 2013, 42, 7111-7119. doi:10.1039/c3dt32408g
- ↑ Williams, Michael L.; Noack, Cassandra L.; Saverin, Rodney J.; Healy, Peter C. "(2-Bromophenyl)diphenylphosphine" Acta Crystallographica, Section E: Structure Reports Online. 2002, Volume 58, pp 306-o307. doi:10.1107/S1600536802002945
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