Triphenylstibine
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Preferred IUPAC name Triphenylstibane | |
Other names Triphenylantimony | |
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ECHA InfoCard | 100.009.125 |
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Properties | |
Chemical 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 |
Related compounds | |
Related compounds | Triphenylamine Triphenylphosphine Triphenylarsine Stibine |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | mildly toxic |
GHS labelling:[1] | |
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) | 1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references |
Chemical compound
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
- ^ "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.
- v
- t
- e
- SbBr3
- Sb(C2H3O2)3
- SbCl3
- SbF3
- Sb4O4(OH)2(NO3)2
- SbH3
- SbI3
- SbN
- Sb2O3
- Sb2S3
- Sb2(SO4)3
- Sb2Se3
- Sb2Te3
Organoantimony(III) compounds |
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- Sb2O4
- SbCl5
- SbF5
- Sb2O5
- Sb2S5
Organoantimony(V) compounds |
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