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Triphenylstibine

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Triphenylstibine
3D structure of PPh3
Names
IUPAC name Triphenylstibine
Other names Triphenylantimony
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.125 Edit this at Wikidata
PubChem CID
RTECS number
  • WJ1400000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N
  • InChI=1/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;/rC18H15Sb/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15HKey: HVYVMSPIJIWUNA-KWOBPOEBAA
SMILES
  • c3c((c1ccccc1)c2ccccc2)cccc3
Properties
Chemical formula C18H15Sb
Molar mass 353.07 g/mol
Appearance Colourless solid
Density 1.53 g/cm
Melting point 52-54 °C
Boiling point 377 °C
Solubility in water insoluble
Structure
Molecular shape trigonal pyramidal
Hazards
Occupational safety and health (OHS/OSH):
Main hazards mildly toxic
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
1
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Triphenylstibine is the chemical compound with the formula Sb(C6H5)3. Abbreviated SbPh3, this colourless solid is often considered the prototypical organoantimony compound. It is used as a ligand in coordination chemistry and as a reagent in organic synthesis.

Like the related molecules triphenylphosphine and triphenylarsine, SbPh3 is pyramidal with a propeller-like arrangement of the phenyl groups. The Sb-C distances average 2.14-2.17 Å and the C-Sb-C angle are 95°.

SbPh3 was first reported in 1886, being prepared from antimony trichloride by the reaction:

6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl

The modern method employs the Grignard method, using phenylmagnesium bromide and SbCl3.

References

  1. Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862
  2. Michaelis, A.; Reese, A. “Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen” Liebigs Annallen der Chemie volume 233, pages 39-60 (1886). DOI: 10.1002/jlac.18862330104.
  3. Hiers, G. S. “Triphenylstibine” Organic Syntheses, Collected Volume 1, p.550 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0550.pdf
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