Triphenylstibine

Triphenylstibine
Names
	IUPAC name Triphenylstibine
	Other names Triphenylantimony
Identifiers
CAS Number	603-36-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	11284 ;
ECHA InfoCard	100.009.125
PubChem CID	11777;
RTECS number	WJ1400000;
UNII	G1X1263AMM ;
CompTox Dashboard (EPA)	DTXSID4052269 ;
	InChI InChI=1S/3C6H5.Sb/c31-2-4-6-5-3-1;/h31-5H; Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N ; 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;
	SMILES c3c([Sb](c1ccccc1)c2ccccc2)cccc3;
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
Hazards
Main hazards	mildly toxic
R-phrases (outdated)	20/22-51/53
S-phrases (outdated)	61
NFPA 704 (fire 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).
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	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[1] 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°.[2]

SbPh₃ was first reported in 1886, being prepared from antimony trichloride by the reaction:[3]

6 Na + 3 C₆H₅Cl + SbCl₃ → (C₆H₅)₃Sb + 6 NaCl

An alternative method treats phenylmagnesium bromide with SbCl₃.[4]

References

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.

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[McAuliffe-1] C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.

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

[3] 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.

[4] Hiers, G. S. (1927). "Triphenylstibine". Organic Syntheses. 7: 80. doi:10.15227/orgsyn.007.0080.