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Triphenylphosphine dibromide

Chemical compound From Wikipedia, the free encyclopedia

Triphenylphosphine dibromide is the organophosphorus compound with the formula (C6H5)3PBr2. It is a white or colorless hygroscopic solid that is used as a brominating agent in organic synthesis. It is prepared by the addition of bromine to triphenylphosphine in an inert solvent. Often it is generated in situ.[1] Triphenylphosphine dibromide is usually depicted as a phosphonium salt with tetrahedral phosphorus cation. According to X-ray crystallography, solid structures can feature halogen bonding.[2]

Quick facts Names, Identifiers ...
Triphenylphosphine dibromide
(C6H5)3PBr+ Br−
Names
Other names
bromotriphenylphosphonium bromide, dibromotriphenylphosphorane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.596 Edit this at Wikidata
UNII
  • InChI=1S/C18H15BrP.BrH/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1
    Key: UWGULZXZFOYYJT-UHFFFAOYSA-M
  • C1=CC=C(C=C1)[P+](C2=CC=CC=C2)(C3=CC=CC=C3)Br.[Br-]
Properties
C18H15Br2P2
Molar mass 453.074 g·mol−1
Appearance White solid
Density 1.194 g/cm3
Melting point 235 °C (455 °F; 508 K)
1.6358
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Illustrative of its use is the conversion of 2-naphthol to 2-bromonaphthalene:[3]

C10H7(OH) + (C6H5)3PBr2 → C10H7Br + (C6H5)3PO + HBr

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