Triphenylstibine

Triphenylstibine

IUPAC name Triphenylstibine
Other names Triphenylantimony
Identifiers
CAS number	603-36-1^Y
PubChem	11777
ChemSpider	11284^Y
RTECS number	WJ1400000
Jmol-3D images	Image 1
SMILES c3c([Sb](c1ccccc1)c2ccccc2)cccc3
InChI InChI=1S/3C6H5.Sb/c31-2-4-6-5-3-1;/h31-5H;^Y Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N^Y InChI=1/3C6H5.Sb/c31-2-4-6-5-3-1;/h31-5H;/rC18H15Sb/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Key: HVYVMSPIJIWUNA-KWOBPOEBAA
Properties
Molecular formula	C₁₈H₁₅Sb
Molar mass	353.07 g/mol
Appearance	Colourless solid
Density	1.53 g/cm³
Melting point	52-54 °C
Boiling point	377 °C
Solubility in water	insoluble
Structure
Molecular shape	trigonal pyramidal
Hazards
R-phrases	20/22-51/53
S-phrases	61
Main hazards	mildly toxic
NFPA 704	0 1 0
Related compounds
Related compounds	Triphenylphosphine Triphenylarsine Stibine
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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