10261. Triphenylbismuth

Nomenclature

CAS number: 603-33-8
Triphenylbismuthine.
C18H15Bi; mol wt 440.29.
C 49.10%, H 3.43%, Bi 47.46%.

Description and references

Homoleptic Bi(III) reagent. Prepn from phenylmagnesium bromide and bismuth halides: P. Pfeiffer et al., Ber. 37, 4620 (1904); A. Classen, O. Ney, Z. Anorg. Allg. Chem. 15, 253 (1921) DOI. Thermal properties: W. V. Steele, J. Chem. Thermodyn. 11, 187 (1979) DOI. Crystal structure: D. M. Hawley, G. Ferguson, J. Chem. Soc. A 1968, 2059 DOI; P. G. Jones et al., Z. Kristallogr. 210, 377 (1995). Synthetic applications in prepn of bismuth thiolates and carboxylates: P. C. Andrews et al., J. Chem. Soc. Dalton Trans. 2002, 4634 DOI. Effects on radiopacity and flexural properties of polymeric dental resins: L. A. Lang et al., J. Prosthodont. 9, 23 (2000) DOI PubMed.

Chemical structure

Properties

Crystals from abs alcohol, mp 77.6°. bp14 242°. d25 1.585. Specific heat capacity: 0.75 J/gK. Sol in methylene chloride, chloroform, carbon tetrachloride, benzene, toluene, ether, THF, ethyl acetate. Insol in water, alcohols. Dec in acidic solvents. Also reported as fine white needles from acetonitrile, crystal d 1.95 (Hawley, Ferguson). LD50 orally in dogs: 180 g/kg (Andrews). Protect from light, moisture and acidic vapors.

Caution

Irritating to eyes, respiratory system.

Use

Radiopacifying agent in dental resins and medical devices. Polymerization catalyst; source of phenyl radicals under photolytic conditions. Catalyst for glycol cleavage; phenylating agent in organic synthesis.