Triphenylstibine
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| Names | |
|---|---|
| Preferred IUPAC name Triphenylstibane | |
| Other names Triphenylantimony | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.009.125 |
| EC Number |
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PubChem CID | |
| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) | |
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| 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 | |
| Related compounds | |
Related compounds | Triphenylamine Triphenylphosphine Triphenylarsine Stibine |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | mildly toxic |
| GHS labelling:[1] | |
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| Danger | |
| H301, H302, H332, H411 | |
| P261, P264, P270, P271, P273, P301+P310, P301+P312, P304+P312, P304+P340, P312, P330, P391, P405 | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Triphenylstibine is the chemical compound with the formula Sb(C6H5)3, which is often abbreviated SbPh3, This colourless solid is a common organoantimony(III) compound. It serves as a ligand in coordination chemistry[2] and as a reagent in organic synthesis.
Like the related molecules triphenylamine, 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 angles are 95°.[3]
Synthesis and reactions
Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene:[4]
- 6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl
In an alternative method, phenylmagnesium bromide is treated with SbCl3.[5]
Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:[6]
- Sb(C6H5)3 + 2SbCl3 → 3Sb(C6H5)Cl2
Stiboranes can be synthesised from triphenylstibine by halogenation:
- Sb(C6H5)3 + Cl2 → Sb(C6H5)3Cl2
As confirmed by X-ray crystallography, Sb(C6H5)3Cl2 features pentacoordinate Sb(V) with trans-diaxial chloride ligands.[7]
References
- ^ "Triphenylantimony". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
- ^ C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
- ^ 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, August; Reese, A. (1886). "Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen". Liebigs Annalen der Chemie. 233: 39-60. doi:10.1002/jlac.18862330104.
- ^ Hiers, G. S. (1927). "Triphenylstibine". Organic Syntheses. 7: 80. doi:10.15227/orgsyn.007.0080.
- ^ Ateş, Mustafa; Breunig, Hans Joachim; Güleç, Sabahittin; Offermann, Werner; Häberle, Karl; Dräger, Martin (1989). "Synthesen und Strukturen von Ethyl-, Propyl-, Butyl- und Mesitylantimon". Chemische Berichte. 122 (3): 473–478. doi:10.1002/cber.19891220313.
- ^ Begley, M. J.; Sowerby, D. B. (1993). "Structures of triphenylantimony(V) dibromide and dichloride". Acta Crystallographica Section C Crystal Structure Communications. 49 (6): 1044–1046. Bibcode:1993AcCrC..49.1044B. doi:10.1107/S0108270192011958.