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

• 64-17-5 ethanol 
• 6729-64-2 tri(p-tolyl)bismuth dichloride 
• 67-64-1 acetone 
• 60-29-7 diethyl ether 
• 51752-29-5 bis(4-methylphenyl)bismuth chloride 
• 106-38-7 para-bromotoluene 
• 594-19-4 tert.-butyl lithium 
• 7787-58-8 bismuth(III) bromide 
• 7440-69-9 bismuth 
• 7787-60-2 bismuth(III) chloride 
• 19028-28-5 di p-tolyl iodonium chloride 
• 29847-06-1 {4-CH₃C₆H₄N₂}CO₂K 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 255831-37-9 [2-(4,4-dimethyl-3,4-dihydrooxaol-2-yl)phenyl]tris(4-methylphenyl)bismuthonium bromide 

Downstream Products

• 537-64-4 bis(p-tolyl)mercury 
• 603-33-8 triphenylbismuthane 
• 2314-79-6 N-(p-tolyl)succinimide 
• 2142-03-2 2-p-tolylisoindoline-1,3-dione 
• 134-84-9 4-Methylbenzophenone 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 13152-94-8 3,4'-dimethylbenzophenone 
• 136935-71-2 β-naphthyl-4-methylphenyl-ketone 
• 13565-37-2 trans-4,4'-dimethylchalcone 
• 50990-40-4 (2E)-3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one 
• 14385-63-8 (E)-3-(furan-2-yl)-1-(4-methylphenyl)prop-2-en-1-one 
• 13565-42-9 3-(3-chlorophenyl)-1-(4-methylphenyl)-(2E)-2-propen-1-one 
• 37620-37-4 (E)-4-chloro-4'-methylchalcone 
• 13565-40-7 3-(4-bromophenyl)-1-(4-methylphenyl)-(2E)-2-propen-1-one 

Relevant articles and documents

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Palladium-Catalyzed Synthesis of α-Diimines from Triarylbismuthines and Isocyanides

In this study, we report a highly selective coupling reaction between triarylbismuthines and isocyanides using palladium diacetate as the catalyst, affording α-diimines, with the formation of three C-C bonds. Among several aryl sources (Ar-YLn: Y = B, Sn, Pb, Sb, Bi, I), only triarylbismuthines successfully undergo coupling with isocyanides to selectively afford α-diimines. The coupling reaction exhibits the advantages of high atom economy and convenient operation, with no need for any additive.

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.