Triphenylbismuthine

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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]

Triphenylbismuthine
Names
Other names
Triphenylbismuth
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.122 Edit this at Wikidata
EC Number
  • 210-033-4
UNII
  • InChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H;
    Key: ZHXAZZQXWJJBHA-UHFFFAOYSA-N
  • C1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3
Properties
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]
GHS07: Exclamation mark
Warning
H302, H312, H332
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).
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]

Chemical structure of triphenylbismuthine dichloride (Ph3BiCl2)
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References

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  1. ^ "Triphenylbismuth". pubchem.ncbi.nlm.nih.gov. Retrieved 9 February 2024.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.