(2-Bromophenyl)diphenylphosphine

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(2-Bromophenyl)diphenylphosphine
BrC6H4PPh2.png
Ball-and-stick model of the (2-bromophenyl)diphenylphosphine molecule
Names
Other names
(o-Bromophenyl)diphenylphosphine; (2-Bromophenyl)diphenylphosphane
Identifiers
3D model (JSmol)
ChemSpider
EC Number 263-515-1
Properties
C18H14BrP
Molar mass 341.19 g·mol−1
Appearance White solid
Melting point 115 °C (239 °F; 388 K)
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[edit]

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[edit]

  1. ^ a b Bennett, Martin A.; Bhargava, Suresh K.; Hockless, David C. R.; Welling, Lee L.; Willis, Anthony C. (1996). "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. 118 (43): 10469. doi:10.1021/ja961511h. 
  2. ^ Zhang, Fushi; Wang, Liduo; Chang, Shih-Han; Huang, Kuan-Lin; Chi, Yun; Hung, Wen-Yi; Chen, Chih-Ming; Lee, Gene-Hsiang; Chou, Pi-Tai (2013). "Phosphorescent Ir(iii) complexes with both cyclometalate chromophores and phosphine-silanolate ancillary: Concurrent conversion of organosilane to silanolate". Dalton Transactions. 42 (19): 7111. doi:10.1039/c3dt32408g. PMID 23518610. 
  3. ^ Williams, Michael L.; Noack, Cassandra L.; Saverin, Rodney J.; Healy, Peter C. (2002). "(2-Bromophenyl)diphenylphosphine". Acta Crystallographica Section E Structure Reports Online. 58 (3): o306–o307. doi:10.1107/S1600536802002945.