(2-Bromophenyl)diphenylphosphine Knowpia

(2-Bromophenyl)diphenylphosphine
Names
	Preferred IUPAC name (2-Bromophenyl)di(phenyl)phosphane
	Other names (o-Bromophenyl)diphenylphosphine
Identifiers
CAS Number	62336-24-7;
3D model (JSmol)	Interactive image;
ChemSpider	101130;
EC Number	263-515-1;
PubChem CID	112836;
UNII	S8AQ9M4YUR ;
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	341.188 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-bromoiodobenzene, 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]

Lithiation with butyl lithium gives o-lithiated triphenylphosphine. The bromide also forms a Grignard reagent. These metallated phosphines are versatile reagents.^[4]

BrC₆H₄PPh₂ + Mg → BrMgC₆H₄PPh₂

2 BrMgC₆H₄PPh₂ + PhPCl₂ → PhP[C₆H₄PPh₂]₂ + 2 MgClBr

References edit

^ ^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.
^ 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): 7111–9. doi:10.1039/c3dt32408g. PMID 23518610.
^ Williams, Michael L.; Noack, Cassandra L.; Saverin, Rodney J.; Healy, Peter C. (2002). "(2-Bromophenyl)diphenylphosphine". Acta Crystallographica Section E. 58 (3): o306–o307. doi:10.1107/S1600536802002945. hdl:10072/6976.
^ Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The preparation and complex-forming properties of one tritertiary and one tetratertiary phosphine", J. Chem. Soc. 1963, 3930. doi:10.1039/JR9630003930

[Ben-1] 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): 7111–9. 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. 58 (3): o306–o307. doi:10.1107/S1600536802002945. hdl:10072/6976.

[4] Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The preparation and complex-forming properties of one tritertiary and one tetratertiary phosphine", J. Chem. Soc. 1963, 3930. doi:10.1039/JR9630003930

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Summary

Preparation edit

References edit