Triphenylstibine
From Wikipedia, the free encyclopedia
| Triphenylstibine | |
|---|---|
 |
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| IUPAC name | Triphenylstibine |
| Other names | Triphenylantimony |
| Identifiers | |
| CAS number | [603-36-1] |
| RTECS number | WJ1400000 |
| Properties | |
| Molecular formula | C18H15Sb |
| Molar mass | 353.07 g/mol |
| Appearance | Colourless solid |
| Density | 1.53 g/cm3 |
| Melting point |
52-54 °C |
| Boiling point |
377 °C |
| Solubility in water | insoluble |
| Structure | |
| Molecular shape | trigonal pyramidal |
| Hazards | |
| Main hazards | mildly toxic |
| NFPA 704 |
 0
1
0
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| R-phrases | 20/22-51/53 |
| S-phrases | 61 |
| Related compounds | |
| Related compounds | Triphenylphosphine Triphenylarsine Stibine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 by the reaction:[2]
- 6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl
The modern method employs the Grignard method, using phenylmagnesium bromide and SbCl3.[3]
[edit] References
- ^ Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862
- ^ 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.
- ^ Hiers, G. S. “Triphenylstibine” Organic Syntheses, Collected Volume 1, p.550 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0550.pdf
