Triphenyl bismuth (Cat No.:I014745) is an organobismuth compound with the chemical formula (C6H5)3Bi. It is a white crystalline powder that is insoluble in water but soluble in organic solvents. Triphenyl bismuth is commonly used as a catalyst in organic synthesis reactions, enabling the formation of carbon-carbon and carbon-heteroatom bonds. It finds applications in various chemical transformations and is valued for its unique reactivity. With its distinctive molecular structure, Triphenyl bismuth plays a significant role in the preparation of diverse organic compounds and contributes to advancements in synthetic chemistry.
Catalog Number | I014745 |
CAS Number | 603-33-8 |
Synonyms | Triphenyl bismuth; NSC 465; NSC-465; NSC465;Bismuthine, triphenyl- |
Molecular Formula | C18H15Bi |
Purity | ≥95% |
Solubility | Soluble in DMSO |
Storage | Room Temperature |
IUPAC Name | triphenylbismuthane |
InChI | InChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H; |
InChIKey | ZHXAZZQXWJJBHA-UHFFFAOYSA-N |
SMILES | C1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3 |
Reference | </br> 1: Plokhikh AV, Falmbigl M, Golovina IS, Akbashev AR, Karateev IA, Presnyakov MY, Vasiliev AL, Spanier JE. Formation of BiFeO(3) from a Binary Oxide Superlattice Grown by Atomic Layer Deposition. Chemphyschem. 2017 Aug 5;18(15):1966-1970. doi: 10.1002/cphc.201700407. Epub 2017 Jun 20. PubMed PMID: 28631872.</br>2: Hiromori Y, Ido A, Aoki A, Kimura T, Nagase H, Nakanishi T. Ligand Activity of Group 15 Compounds Possessing Triphenyl Substituent for the RXR and PPARγ Nuclear Receptors. Biol Pharm Bull. 2016;39(10):1596-1603. PubMed PMID: 27725436.</br>3: Fernández J, Amestoy H, Sardon H, Aguirre M, Varga AL, Sarasua JR. Effect of molecular weight on the physical properties of poly(ethylene brassylate) homopolymers. J Mech Behav Biomed Mater. 2016 Dec;64:209-19. doi: 10.1016/j.jmbbm.2016.07.031. Epub 2016 Aug 2. PubMed PMID: 27517665.</br>4: Bučinský L, Jayatilaka D, Grabowsky S. Importance of Relativistic Effects and Electron Correlation in Structure Factors and Electron Density of Diphenyl Mercury and Triphenyl Bismuth. J Phys Chem A. 2016 Aug 25;120(33):6650-69. doi: 10.1021/acs.jpca.6b05769. Epub 2016 Aug 16. PubMed PMID: 27434184.</br>5: Goswami M, Ashley DC, Baik MH, Pohl NL. Mechanistic Studies of Bismuth(V)-Mediated Thioglycoside Activation Reveal Differential Reactivity of Anomers. J Org Chem. 2016 Jul 15;81(14):5949-62. doi: 10.1021/acs.joc.6b00860. Epub 2016 Jun 24. PubMed PMID: 27295299.</br>6: Weis F, Seipenbusch M, Kasper G. Film Growth Rates and Activation Energies for Core-Shell Nanoparticles Derived from a CVD Based Aerosol Process. Materials (Basel). 2015 Mar 6;8(3):966-976. doi: 10.3390/ma8030966. PubMed PMID: 28787982; PubMed Central PMCID: PMC5455439.</br>7: Islam A, Da Silva JG, Berbet FM, da Silva SM, Rodrigues BL, Beraldo H, Melo MN, Frézard F, Demicheli C. Novel triphenylantimony(V) and triphenylbismuth(V) complexes with benzoic acid derivatives: structural characterization, in vitro antileishmanial and antibacterial activities and cytotoxicity against macrophages. Molecules. 2014 May 12;19(5):6009-30. doi: 10.3390/molecules19056009. PubMed PMID: 24824136.</br>8: Berger RJ, Rettenwander D, Spirk S, Wolf C, Patzschke M, Ertl M, Monkowius U, Mitzel NW. Relativistic effects in triphenylbismuth and their influence on molecular structure and spectroscopic properties. Phys Chem Chem Phys. 2012 Nov 28;14(44):15520-4. doi: 10.1039/c2cp43471g. Epub 2012 Oct 17. PubMed PMID: 23072773.</br>9: Anjaneyulu O, Maddileti D, Kumara Swamy KC. Structural motifs in phenylbismuth heterocyclic carboxylates–secondary interactions leading to oligomers. Dalton Trans. 2012 Jan 21;41(3):1004-12. doi: 10.1039/c1dt11207d. Epub 2011 Nov 21. PubMed PMID: 22105914.</br>10: Xu H, Abdulghani S, Behiri J, Sabokbar A. Osteolytic potential of triphenyl bismuth as an alternative contrast medium in acrylic bone cement. J Biomed Mater Res B Appl Biomater. 2005 Oct;75(1):64-73. PubMed PMID: 16015616.</br>11: Abdulghani SN, Nazhat SN, Behiri JC, Deb S. Effect of triphenyl bismuth on glass transition temperature and residual monomer content of acrylic bone cements. J Biomater Sci Polym Ed. 2003;14(11):1229-42. PubMed PMID: 14768910.</br>12: Thurston JH, Whitmire KH. Molecular precursors for ferroelectric materials: synthesis and characterization of Bi2M2(mu-O)(sal)4(Hsal)4(OEt)2 and BiM4(mu-O)4(sal)4(Hsal)3(O(i)Pr)4 (sal = O2CC6H4O, Hsal = O2CC6H4OH) (M = Nb, Ta). Inorg Chem. 2003 Mar 24;42(6):2014-23. PubMed PMID: 12639136.</br>13: Arata T, Oyama Y, Tabaru K, Satoh M, Hayashi H, Ishida S, Okano Y. Cytotoxic effects of triphenylbismuth on rat thymocytes: comparisons with bismuth chloride and triphenyltin chloride. Environ Toxicol. 2002 Oct;17(5):472-7. PubMed PMID: 12242678.</br>14: Deb S, Abdulghani S, Behiri JC. Radiopacity in bone cements using an organo-bismuth compound. Biomaterials. 2002 Aug;23(16):3387-93. PubMed PMID: 12099281.</br>15: Lang LA, Mattie PA, Rawis HR. The effect of triphenylbismuth on the radiopacity and performance properties of compression- and injection-molded denture resins. J Prosthodont. 2000 Mar;9(1):23-9. PubMed PMID: 11074025.</br>16: Rawls HR, Granier RJ, Smid J, Cabasso I. Thermomechanical investigation of poly(methylmethacrylate) containing an organobismuth radiopacifying additive. J Biomed Mater Res. 1996 Jul;31(3):339-43. PubMed PMID: 8806059.</br>17: Mattie PA, Rawls HR, Cabasso I. Development of a radiopaque, autopolymerizing dental acrylic resin. J Prosthodont. 1994 Dec;3(4):213-8. PubMed PMID: 7866504.</br>18: Rawls HR, Marshall MV, Cardenas HL, Bhagat HR, Cabasso I. Cytotoxicity evaluation of a new radiopaque resin additive–triphenyl bismuth. Dent Mater. 1992 Jan;8(1):54-9. PubMed PMID: 1521685.</br>19: ADLOFF-BACHER M, ADLOFF JP. [ON THE LABELLING OF TRIPHENYL-BISMUTH BY RADIOACTIVE BISMUTH: CHROMATOGRAPHIC STUDY]. J Chromatogr. 1964 Jun;14:70-5. French. PubMed PMID: 14194377.</br></br> |