Triphenylbismuthine

Triphenylbismuthine
Names
	Other names Triphenylbismuth
Identifiers
CAS Number	603-33-8 ;
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/c31-2-4-6-5-3-1;/h31-5H; 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:
Pictograms
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

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 C₆H₅MgBr₃ → Bi(C₆H₅)₃ + 3 MgBrCl

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]

Related compounds

^ "Triphenylbismuth". pubchem.ncbi.nlm.nih.gov. Retrieved 9 February 2024.
^ Finet, Jean-Pierre; Rao, Maddali L. N. (2013). "Triphenylbismuthine". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt358.pub2. ISBN 978-0-471-93623-7.
^ Jones, P. G.; Blaschette, A.; Henschel, D.; Weitze, A. (1995). "Redetermination of the Crystal Structure of Triphenylbismuth, (C₆H₅)₃Bi". Zeitschrift für Kristallographie - Crystalline Materials. 210 (5): 377–378. Bibcode:1995ZK....210..377J. doi:10.1524/zkri.1995.210.5.377.
^ Rao, Maddali L. N.; Jadhav, Deepak N.; Dasgupta, Priyabrata (2010). "Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles". Organic Letters. 12 (9): 2048–2051. doi:10.1021/ol1004164. PMID 20377270.
^ Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J.R. (1999). "An Efficient Method for the Preparation of Bismuth(III) Trifluoromethanesulfonate". Tetrahedron Letters. 40 (2): 285–286. doi:10.1016/s0040-4039(98)02397-1.
^ Hawley, David M.; Ferguson, George (1968). "The stereochemistry of some organic derivatives of Group VB elements. Part II. The crystal and molecular structure of triphenylbismuth dichloride". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 2539. doi:10.1039/J19680002539.