Triphenylstibine

Triphenylstibine

Names
IUPAC name Triphenylstibine
Other names Triphenylantimony
Identifiers
CAS Number	603-36-1 Y
3D model (Jmol)	Interactive image
ChemSpider	11284 Y
ECHA InfoCard	100.009.125
PubChem	11777
RTECS number	WJ1400000
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/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	20/22-51/53
S-phrases	61
NFPA 704	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 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