Triphenylstibine
Appearance
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Names | |
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Preferred IUPAC name
Triphenylstibane | |
Other names
Triphenylantimony
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.009.125 |
EC Number |
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PubChem CID
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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
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Triphenylamine Triphenylphosphine Triphenylarsine Stibine |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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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).
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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[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 angle are 95°.[3]
SbPh3 was first reported in 1886, being prepared from antimony trichloride by the reaction:[4]
- 6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl
An alternative method treats phenylmagnesium bromide with SbCl3.[5]
References
[edit]- ^ "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, 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. (1927). "Triphenylstibine". Organic Syntheses. 7: 80. doi:10.15227/orgsyn.007.0080.