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Triphenylstibine

Triphenylstibine

General
Systematic name	Triphenylstibine
Other names	Triphenylantimony
Molecular formula	C₁₈H₁₅Sb
SMILES
Molar mass	353.07 g/mol
Appearance	Colourless solid
CAS number	603-36-1
Properties
Density and phase	1.53 g/cm³
Solubility in water	insoluble
Other solvents	most organic solvents
Melting point	52-54 °C
Boiling point	377 °C
Structure
Molecular shape	trigonal pyramidal
Dipole moment	? D
Hazards
MSDS
Main hazards	mildly toxic
NFPA 704	0 1 0
R/S statement	R: 20/22-51/53 S:61
RTECS number	WJ1400000
Supplementary data page
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

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.

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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]

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

Category: Antimony compounds