Triphenylbismuthine

Triphenylbismuthine is an organobismuth compound with the formula Bi(C₆H₅)₃. It is a white, air-stable solid that is soluble in organic solvents. It is prepared by treatment of bismuth trichloride with phenylmagnesium bromide.^[2]

BiCl₃ + 3 C₆H₅MgBr → Bi(C₆H₅)₃ + 3 MgBrCl

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Triphenylbismuthine

Names
Other names Triphenylbismuth
Identifiers
CAS Number	603-33-8 Y
3D model (JSmol)	Interactive image
ChemSpider	11281
ECHA InfoCard	100.009.122
EC Number	210-033-4
PubChem CID	11774
UNII	R18732F41W
CompTox Dashboard (EPA)	DTXSID6042498
InChI InChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H; Key: ZHXAZZQXWJJBHA-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3
Properties
Chemical formula	C18H15Bi
Molar mass	440.298 g·mol−1
Appearance	white solid
Density	1.585 g/cm³
Melting point	77.6 °C (171.7 °F; 350.8 K)
Hazards
GHS labelling:[1]
Pictograms	‹ The template below (GHS exclamation mark) is being considered for merging with GHS pictogram. See templates for discussion to help reach a consensus. ›
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Related compounds
Other cations	triphenylphosphine triphenylarsine triphenylstibine
Related compounds	pentaphenylbismuth
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Structurally it resembles related compounds such as triphenylstibine. The C-Bi-C angles are 94°.^[3]

Triphenylbismuthine serves as a phenyl donor in some cross coupling reactions catalyzed by Pd(0) complexes.^[4] It reacts with trifluoromethanesulfonic acid to give bismuth triflate:^[5]

Bi(C₆H₅)₃ + 3 HO₃SCF₃ → Bi(O₃SCF₃)₃ + 3 C₆H₆

Triphenylbismuthine readily undergoes oxidative addition to form Bi(V) derivatives such as triphenylbismuthine dichloride.^[6]