(2-Bromophenyl)diphenylphosphine

(2-Bromophenyl)diphenylphosphine
Names
	Other names (o-Bromophenyl)diphenylphosphine, (2-Bromophenyl)diphenylphosphane
Identifiers
CAS Number	62336-24-7;
3D model (JSmol)	Interactive image;
ChemSpider	101130;
EC Number	263-515-1;
PubChem CID	112836;
CompTox Dashboard (EPA)	DTXSID60211392 ;
	InChI InChI=1S/C18H14BrP/c19-17-13-7-8-14-18(17)20(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H Key: XIONUQPOXCUMMB-UHFFFAOYSA-N; InChI=1/C18H14BrP/c19-17-13-7-8-14-18(17)20(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H Key: XIONUQPOXCUMMB-UHFFFAOYAI;
	SMILES c1ccc(cc1)P(c2ccccc2)c3ccccc3Br;
Properties
Chemical formula	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

^ ^a ^b 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

[Ben-1] 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

[2] 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

[3] 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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