5142-75-6

Basic information

• Product Name: TRI-P-TOLYLBISMUTHINE
• Synonyms: TRIS(P-TOLYL)BISMUTHINE;TRI-P-TOLYLBISMUTHINE;TRIS(4-TOLYL)BISMUTH;TRIS(4-METHYLPHENYL)BISMUTHINE;Bismuthine,tris[4-methylphenyl]-;Tris(4-methylphenyl)bismuthine Tris(p-tolyl)bismuthine;Tris(4-methylphenyl) bismuth;Tri-p-tolylbismuthine
• CAS NO: 5142-75-6
• Molecular Formula: C₂₁H₂₁Bi
• Molecular Weight: 482.37
• Product Categories: Bi (Bismuth) Compounds;Classes of Metal Compounds;Semimetal Compounds
• Mol File: 5142-75-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 119 °C
• Appearance: /
• Solubility: almost transparency in THF
• CAS DataBase Reference: TRI-P-TOLYLBISMUTHINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-P-TOLYLBISMUTHINE(5142-75-6)
• EPA Substance Registry System: TRI-P-TOLYLBISMUTHINE(5142-75-6)

Safety Data

• Hazardous Substances Data: 5142-75-6(Hazardous Substances Data)

Usage

General Description

TRI-P-TOLYLBISMUTHINE, also known as tri-p-tolylbismuth or bis(p-tolyl)bismuth, is an organobismuth compound with the chemical formula (C6H4CH3)3Bi. It is a white crystalline solid that is primarily used as a reagent in organic synthesis. TRI-P-TOLYLBISMUTHINE is widely known for its applications in creating carbon-bismuth bonds and in the synthesis of organic bismuth compounds. It has also been used in catalytic processes and as a precursor in the production of other bismuth-containing compounds. Additionally, this compound has potential in medicinal chemistry as a precursor for bismuth-based pharmaceuticals due to its low toxicity compared to other heavy metals.

InChI:InChI=1/3C7H7.Bi/c3*1-7-5-3-2-4-6-7;/h3*3-6H,1H3;/rC21H21Bi/c1-16-4-10-19(11-5-16)22(20-12-6-17(2)7-13-20)21-14-8-18(3)9-15-21/h4-15H,1-3H3

Upstream product

• 106-38-7 para-bromotoluene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 60-29-7 diethyl ether 
• 51752-29-5 bis(4-methylphenyl)bismuth chloride 
• 703-55-9 1-naphthylmagnesiumbromide 
• 594-19-4 tert.-butyl lithium 
• 7787-58-8 bismuth(III) bromide 
• 313974-01-5 (CH₃C₆H₄)3BiNSO₂C₆H₅ 
• 121900-05-8 iodobis(4-methylphenyl)bismuthane 
• 128816-64-8 sodium 4-methylbenzenecarboselenoate 
• 128816-65-9 sodium 4-methoxybenzenecarboselenoate 
• 858520-14-6 p-Tol₃Bi(OSO₂C₆H₃Me₂-2,4)2 
• 858520-13-5 tri-p-tolylbismuth (2,5-dimethylbenzenesulfonato)2 
• 107536-32-3 tris(4-methylphenyl)bismuth diacetate 

Downstream Products

• 537-64-4 bis(p-tolyl)mercury 
• 603-33-8 triphenylbismuthane 
• 2142-03-2 2-p-tolylisoindoline-1,3-dione 
• 19482-11-2 4-chloro-4'-methylbiphenyl 
• 1517-63-1 (R)-(4-Methylphenyl)phenylmethanol 
• 162300-69-8 (+)-(S)-4-chlorophenyl-4'-methylphenylmethanol 
• 808740-71-8 (S)-(4-methoxyphenyl)-(4'-methylphenyl)methanol 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 2143-88-6 4-nitro-4'-methyl-1,1'-biphenyl 
• 5748-38-9 4-acetyl-4'-methylbiphenyl 
• 106508-97-8 ethyl 4'-methyl-[1,1'-biphenyl]-4-carboxylate 
• 53040-92-9 4-(4-tolyl)anisole 
• 63283-56-7 4-benzoyl-4'-methylbiphenyl 
• 97067-18-0 4'-methyl-4-trifluoromethyl-biphenyl 

Relevant articles and documents

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Stability and toxicity of tris-tolyl bismuth(v) dicarboxylates and their biological activity towards Leishmania major

A series of 29 tris-tolyl bismuth(v) di-carboxylato complexes of composition [Bi(Tol)3(O2CR)2] involving either ortho, meta or para substituted tolyl ligands have been synthesized and characterised. Of these 15 were assessed for their toxicity towards Leishmania promastigotes and human fibroblast cells, with ten then being subsequently assessed against parasite amastigotes. The carboxylate ligands are drawn from a series of substituted and biologically relevant benzoic acids which allow a comparison with earlier studies on [BiPh3(O2CR)2] and analogous Sb(v) [SbAr3(O2CR)2] (Ar = Ph and Tol) complexes. Twelve complexes have been structurally characterized by single crystal X-ray diffraction and shown to adopt a typical trigonal bipyramidal geometry in which the three tolyl ligands occupy the equatorial plane. NMR studies on two illustrative examples indicate that the complexes are stable in D2O and DMSO but only have a half-life of 1.2 hours in culture medium, with glucose being a contributing factor in decomposition and reduction to Bi(Tol)3. Despite their short lifetime many complexes show significant toxicity towards promastigotes at low concentration (3(O2CC6H3(2-OH,5-C6H3(2,4-F2)))2] and 838 for [Bi(m-Tol)3(O2CC6H4(2-OAc))2]. Best activity and selectivity is observed with complexes containing o- and m-tolyl ligands, and it appears the primary influence on fibroblast toxicity is the Ar ligand while the carboxylate influences promastigote toxicity. The complexes are less effective in vitro against the parasite amastigotes, where longer incubation times and harsher chemical and biological environments are encountered in the assay. Nevertheless, there were some statistically relevant differences at 1 μM against the positive controls with the best performing complexes being [Bi(o-Tol)3(O2CC6H4(2-EtO))2] and [Bi(m-Tol)3(O2CC6H4(2-OAc))2].

Synthesis of highly functionalized diaryl ethers by copper-mediated O-arylation of phenols using trivalent arylbismuth reagents

Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. Highly functionalized diaryl ethers were prepared by a copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes (see scheme). The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. FG=functional group.