Triphenylstibine

Triphenylstibine
Ball-and-stick model of the triphenylstibine molecule
Names
IUPAC name
Triphenylstibine
Other names
Triphenylantimony
Identifiers
603-36-1 YesY
ChemSpider 11284 YesY
Jmol interactive 3D Image
PubChem 11777
RTECS number WJ1400000
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
Hazards
Main hazards mildly toxic
R-phrases 20/22-51/53
S-phrases 61
NFPA 704
Flammability (red): no hazard code Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
1
Related compounds
Related compounds
Triphenylphosphine
Triphenylarsine
Stibine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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 reaction, using phenylmagnesium bromide and SbCl3.[3]

References

  1. Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862
  2. 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.
  3. Hiers, G. S. "Triphenylstibine" Organic Syntheses, Collected Volume 1, p.550 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0550.pdf
This article is issued from Wikipedia - version of the Monday, November 02, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.