278172-59-1

Basic information

• Product Name: methyltriphenylbismuthonium tetrafluoroborate
• Synonyms: methyltriphenylbismuthonium tetrafluoroborate
• CAS NO: 278172-59-1
• Molecular Weight: 542.137
• Mol File: 278172-59-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyltriphenylbismuthonium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: methyltriphenylbismuthonium tetrafluoroborate(278172-59-1)
• EPA Substance Registry System: methyltriphenylbismuthonium tetrafluoroborate(278172-59-1)

Safety Data

• Hazardous Substances Data: 278172-59-1(Hazardous Substances Data)

Upstream product

• 420-37-1 trimethoxonium tetrafluoroborate 
• 603-33-8 triphenylbismuthane 
• 278172-61-5 methyltris(4-methylphenyl)bismuthonium tetrafluoroborate 
• 14104-20-2 silver tetrafluoroborate 
• 74-88-4 methyl iodide 
• 13755-29-8 sodium tetrafluoroborate 
• 13061-96-6 dihydroxy-methyl-borane 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 

Downstream Products

• 67-56-1 methanol 
• 115-10-6 Dimethyl ether 
• 160142-36-9 2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate 
• 603-33-8 triphenylbismuthane 
• 598-53-8 isopropyl methyl ether 
• 538-86-3 benzyl methyl ether 
• 540-67-0 ethyl methyl ether 
• 93-58-3 benzoic acid methyl ester 
• 3112-85-4 methylphenylsulfonate 
• 3802-09-3 methyltriphenylstibonium tetrafluoroborate 
• 277306-39-5 1-(methylthio)ethyleneiminium tetrafluoroborate 
• 108202-20-6 diphenyl(4-methylphenyl)bismuthane 

Relevant articles and documents

Synthesis, structure, and reactions of triaryl(methyl)bismuthonium salts

Treatment of triarylbismuth difluorides 2 (Ar3BiF2; a, Ar = Ph; b, Ar = 4-MeC6H4; c, Ar = 4-MeOC6H4; d, Ar = 2-MeOC6H4) with methylboronic acid (3) in the presence of BF3·OEt2 in CH2Cl2 afforded the corresponding triaryl(methyl)bismuthonium tetrafluoroborates 4a-d ([Ar3MeBi+][BF4-]) in 42-91% yield. X-ray crystallographic analysis of compound 4d revealed that the bismuth center possesses a distorted tetrahedral geometry with C-Bi-C bond angles of 106.1(3)-113.6(3)° and Bi-C bond lengths of 2.182(7)-2.195(8) angstrom. Compound 4a transferred the methyl group to Ph3E (E = P, As, Sb), tris(4-methylphenyl)bismuthine, ROH (R = Me, Et, i-Pr, PhCH2), water, sodium benzenesulfinate, sodium benzoate, N,N-dimethylformamide (DMF), and thioacetamide to give the corresponding methylated products with a good recovery of triphenylbismuthine. The pseudo-first-order rate constant (kobsd = 2.9 × 10-4 s-1) observed for the reaction between 4a and benzyl alcohol (5d) was about twice as large as that (kobsd = 1.3 × 10-4 s-1) between MeOTf and 5d (in CDCl3 at 23°C; [4a] or [MeOTf] = 0.062 M; [5d] = 0.97 M). The observed reactivity of 4a clearly demonstrates the high nucleofugality of the triphenylbismuthonio group.