3802-09-3

Basic information

• Product Name: methyltriphenylstibonium tetrafluoroborate
• Synonyms: methyltriphenylstibonium tetrafluoroborate
• CAS NO: 3802-09-3
• Molecular Weight: 454.907
• Mol File: 3802-09-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyltriphenylstibonium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: methyltriphenylstibonium tetrafluoroborate(3802-09-3)
• EPA Substance Registry System: methyltriphenylstibonium tetrafluoroborate(3802-09-3)

Safety Data

• Hazardous Substances Data: 3802-09-3(Hazardous Substances Data)

Upstream product

• 420-37-1 trimethoxonium tetrafluoroborate 
• 603-36-1 triphenylantimony 
• 278172-59-1 methyltriphenylbismuthonium tetrafluoroborate 
• 33756-93-3 methyltetraphenylstibine 
• 109-63-7 trifluoroborane diethyl ether 

Downstream Products

• 603-36-1 triphenylantimony 
• 30982-88-8 methyldiphenylstibane 
• 38073-71-1 (C₆H₅)2Sb-i-C₃H₇ 
• 38073-70-0 (C₆H₅)2Sb(C₃H₇)Br₂ 
• 38073-68-6 (C₆H₅)2(C₂H₅)SbBr₂ 
• 53235-24-8 (C₆H₅)2(CH₂CHCH₂)Sb 
• 38073-69-7 (C₆H₅)2Sb-i-C₃H₇ 
• 38073-67-5 diphenylethylstibine 
• 38073-50-6 (C₆H₅)(CH₃)Sb(i-C₃H₇) 
• 17585-86-3 dimethyl(phenyl)stibine 
• 38073-47-1 methylethylphenylstibine 

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.