Triphenylstibine

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Triphenylstibine
3D structure of PPh3
Identifiers
CAS number 603-36-1 YesY
PubChem 11777
ChemSpider 11284 YesY
RTECS number WJ1400000
Jmol-3D images Image 1
Properties
Molecular formula C18H15Sb
Molar mass 353.07 g/mol
Appearance Colourless solid
Density 1.53 g/cm3
Melting point 52 to 54 °C (126 to 129 °F; 325 to 327 K)
Boiling point 377 °C (711 °F; 650 K)
Solubility in water insoluble
Structure
Molecular shape trigonal pyramidal
Hazards
R-phrases 20/22-51/53
S-phrases 61
Main hazards mildly toxic
NFPA 704
Flammability (red): no hazard code Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds Triphenylphosphine
Triphenylarsine
Stibine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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°.[1]

SbPh3 was first reported in 1886, being prepared from antimony trichloride by the reaction:[2]

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

The modern method employs the Grignard reaction, using phenylmagnesium bromide and SbCl3.[3]

References[edit]

  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