Triphenylstibine
 | |
| Names | |
|---|---|
| IUPAC name
Triphenylstibine | |
| Other names
Triphenylantimony | |
| Identifiers | |
603-36-1  | |
| ChemSpider | 11284 |
| Jmol interactive 3D | Image |
| PubChem | 11777 |
| RTECS number | WJ1400000 |
| |
| |
| Properties | |
| 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) |
| insoluble | |
| Structure | |
| trigonal pyramidal | |
| Hazards | |
| Main hazards | mildly toxic |
| R-phrases | 20/22-51/53 |
| S-phrases | 61 |
| NFPA 704 | |
| Related compounds | |
| Related compounds |
Triphenylphosphine Triphenylarsine Stibine |
| Except where otherwise noted, 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
- ↑ 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
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