(2-Bromophenyl)diphenylphosphine

(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.

(2-Bromophenyl)diphenylphosphine

Ball-and-stick model of the (2-bromophenyl)diphenylphosphine molecule
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 Y
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

Preparation

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