(2-Bromophenyl)diphenylphosphine

Chemical compound From Wikipedia, the free encyclopedia

(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.

Quick facts Names, Identifiers ...
(2-Bromophenyl)diphenylphosphine
Ball-and-stick model of the (2-bromophenyl)diphenylphosphine molecule
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
3D model (JSmol)
ChemSpider
EC Number
  • 263-515-1
UNII
  • 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
  • c1ccc(cc1)P(c2ccccc2)c3ccccc3Br
Properties
C18H14BrP
Molar mass 341.188 g·mol−1
Appearance White solid
Melting point 115 Â°C (239 Â°F; 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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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

References

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