Triphenylstibine

Chembox new
Name = Triphenylstibine
ImageFile = Triphenylphosphine-3D-sticks.png ImageName = 3D structure of PPh₃
IUPACName = Triphenylstibine
OtherNames = Triphenylantimony
Section1 = Chembox Identifiers
CASNo = 603-36-1
RTECS = WJ1400000
Section2 = Chembox Properties
Formula = C₁₈H₁₅Sb
MolarMass = 353.07 g/mol
Appearance = Colourless solid
Density = 1.53 g/cm³
Solubility = insoluble
MeltingPt = 52-54 °C
BoilingPt = 377 °C
Section3 = Chembox Structure
MolShape = trigonal pyramidal
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = mildly toxic
NFPA-H = 1
NFPA-F =
NFPA-R =
RPhrases = 20/22-51/53
SPhrases = 61
Section8 = Chembox Related
OtherCpds = Triphenylphosphine
Triphenylarsine
Stibine

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°. [Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862]

SbPh₃ was first reported in 1886, being prepared by the reaction: [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.] :6 Na + 3 C₆H₅Cl + SbCl₃ → (C₆H₅)₃Sb + 6 NaClThe modern method employs the Grignard method, using phenylmagnesium bromide and SbCl₃. [Hiers, G. S. “Triphenylstibine” Organic Syntheses, Collected Volume 1, p.550 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0550.pdf]

References