Triphenylstibine

Triphenylstibine

Names
Preferred IUPAC name Triphenylstibane
Other names Triphenylantimony
Identifiers
CAS Number	603-36-1^Y
3D model (JSmol)	Interactive image
ChemSpider	11284^Y
ECHA InfoCard	100.009.125
EC Number	210-037-6
PubChem CID	11777
RTECS number	WJ1400000
UNII	G1X1263AMM^Y
CompTox Dashboard (EPA)	DTXSID4052269
InChI InChI=1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;^Y Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N^Y InChI=1/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;/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/cm^3
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
Related compounds
Related compounds	Triphenylamine Triphenylphosphine Triphenylarsine Stibine
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	mildly toxic
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H332, H411
Precautionary statements	P261, P264, P270, P271, P273, P301+P310, P301+P312, P304+P312, P304+P340, P312, P330, P391, P405
NFPA 704 (fire diamond)	1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Triphenylstibine is the chemical compound with the formula Sb(C₆H₅)₃, which is often abbreviated SbPh₃, This colourless solid is a common organoantimony(III) compound. It serves as a ligand in coordination chemistry^[2] and as a reagent in organic synthesis.

Like the related molecules triphenylamine, 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 angles are 95°.^[3]

Synthesis and reactions

Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene:^[4]

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

In an alternative method, phenylmagnesium bromide is treated with SbCl₃.^[5]

Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:^[6]

Sb(C₆H₅)₃ + 2SbCl₃ → 3Sb(C₆H₅)Cl₂

Stiboranes can be synthesised from triphenylstibine by halogenation:

Sb(C₆H₅)₃ + Cl₂ → Sb(C₆H₅)₃Cl₂

As confirmed by X-ray crystallography, Sb(C₆H₅)₃Cl₂ features pentacoordinate Sb(V) with trans-diaxial chloride ligands.^[7]

References

1. "Triphenylantimony". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
2. C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
3. Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of Triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862
4. Michaelis, August; Reese, A. (1886). "Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen". Liebigs Annalen der Chemie. 233: 39-60. doi:10.1002/jlac.18862330104.
5. Hiers, G. S. (1927). "Triphenylstibine". Organic Syntheses. 7: 80. doi:10.15227/orgsyn.007.0080.
6. Ateş, Mustafa; Breunig, Hans Joachim; Güleç, Sabahittin; Offermann, Werner; Häberle, Karl; Dräger, Martin (1989). "Synthesen und Strukturen von Ethyl-, Propyl-, Butyl- und Mesitylantimon". Chemische Berichte. 122 (3): 473–478. doi:10.1002/cber.19891220313.
7. Begley, M. J.; Sowerby, D. B. (1993). "Structures of triphenylantimony(V) dibromide and dichloride". Acta Crystallographica Section C Crystal Structure Communications. 49 (6): 1044–1046. Bibcode:1993AcCrC..49.1044B. doi:10.1107/S0108270192011958.