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Triphenylbismuth CAS 603-33-8 Bismuthine, triphenyl- CAS no 603-33-8 BISMUTH TRIPHENYL TRIPHENYLBISMUTHINE Triphenylbismuth CAS 603-33-8 Bismuthine, triphenyl- IN Stock CAS 603-33-8 Bismuthine, triphenyl- Triphenylbismuth COA TDS price MSDS
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inquiryCAS No. 603-33-8 Other Names TPB MF C18H15Bi EINECS No. 210-033-4 Type Pharmaceutical Intermediates Appearance:White crystal Stora
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inquiryConditions | Yield |
---|---|
In diethyl ether byproducts: C6H5HgBr; 12h; distillation of ether phase; | 100% |
triphenylbismuthane
Conditions | Yield |
---|---|
In not given byproducts: SO2; 4h at 216°C under 1E-2 - 1E-3 Torr; | 100% |
dibromotriphenylbismuth
triphenylbismuthane
Conditions | Yield |
---|---|
In ethanol 1h reflux; | 100% |
With potassium hydroxide In water 5h reflux or shaking; | |
With ammonia In ethanol byproducts: sulfur; | |
With NH3 In ethanol byproducts: sulfur; |
triphenylbismuth difluoride
triphenylbismuthane
Conditions | Yield |
---|---|
In ethanol 1h reflux; | 100% |
in alkaline medium; | |
in alkaline medium; |
triphenylbismuth dichloride
triphenylbismuthane
Conditions | Yield |
---|---|
In ethanol 1h reflux; | 100% |
With sodium hydrogensulfite In acetone at 0°C; | 80% |
With potassium hydroxide In ethanol 5h reflux or shaking; |
Conditions | Yield |
---|---|
In not given decomposition at room temp.; | A 100% B 100% |
triphenylbismuthane
Conditions | Yield |
---|---|
In not given byproducts: SO2; 4h at 190°C under 1E-2 - 1E-3 Torr; | 100% |
Conditions | Yield |
---|---|
With isopropyl alcohol In not given byproducts: C6H6, acetone; at 20°C; | 100% |
In pyridine byproducts: benzene, arine=arin(germ.); decomposition in pyridine; | 100% |
With phenol In not given byproducts: C6H6, C6H5OH, diphenylether; | 90% |
2,6-di-tert-butyl-4-methylpyridine
methyltriphenylbismuthonium tetrafluoroborate
A
methanol
B
Dimethyl ether
C
2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
D
triphenylbismuthane
Conditions | Yield |
---|---|
With H2O In chloroform-d1 water was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and mixt. was allowed to stand at room temp. for 33 h; detn. by NMR; | A 30% B 16% C 100% D 100% |
2,6-di-tert-butyl-4-methylpyridine
methyltriphenylbismuthonium tetrafluoroborate
isopropyl alcohol
A
isopropyl methyl ether
B
2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
C
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 alcohol was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and allowed to react at 23°C for 4-7 h; detn. by NMR; | A 82% B 100% C 100% |
2,6-di-tert-butyl-4-methylpyridine
methyltriphenylbismuthonium tetrafluoroborate
benzyl alcohol
A
benzyl methyl ether
B
2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
C
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 Kinetics; alcohol was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and allowed to react at 23°C for 4-7 h; detn. by NMR; | A 95% B 100% C 100% |
methanol
2,6-di-tert-butyl-4-methylpyridine
methyltriphenylbismuthonium tetrafluoroborate
A
Dimethyl ether
B
2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
C
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 alcohol was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and allowed to react at 23°C for 4-7 h; detn. by NMR; | A 69% B 100% C 100% |
2,6-di-tert-butyl-4-methylpyridine
ethanol
methyltriphenylbismuthonium tetrafluoroborate
A
ethyl methyl ether
B
2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
C
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 alcohol was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and allowed to react at 23°C for 4-7 h; detn. by NMR; | A 74% B 100% C 100% |
methyltriphenylbismuthonium tetrafluoroborate
triphenylphosphine
B
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 react. (Ph3BiMe)(BF4) and PPh3 in CDCl3 at room temp.; detn. by 1H NMR; | A 100% B 100% |
methyltriphenylbismuthonium tetrafluoroborate
N,N-dimethyl-formamide
A
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 mixt. (Ph3BiMe)(BF4), DMF, and CDCl3 was allowed to stand at room temp.for 1 h; detn. by NMR; | A 100% B 100% |
methyltriphenylbismuthonium tetrafluoroborate
triphenyl-arsane
A
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 react. (Ph3BiMe)(BF4) and AsPh3 in CDCl3 at room temp.; detn. by 1H NMR; | A 100% B 100% |
methyltriphenylbismuthonium tetrafluoroborate
triphenylantimony
A
methyltriphenylstibonium tetrafluoroborate
B
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 react. (Ph3BiMe)(BF4) and SbPh3 in CDCl3 at room temp.; detn. by 1H NMR; | A 100% B 100% |
methyltriphenylbismuthonium tetrafluoroborate
thioacetamide
A
1-(methylthio)ethyleneiminium tetrafluoroborate
B
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 mixt. (Ph3BiMe)(BF4), thioacetamide, and CDCl3 was allowed to react at room temp. for 1 min; detn. by NMR; | A 100% B 100% |
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 Kinetics; byproducts: i-PrOC(O)C2H4OSO2CF3; sample soln. decompn. at 25°C; (1)H-NMR monitoring; | 100% |
Nitrosobenzene
A
triphenylbismuthane
B
(E)-2,2,7,7-Tetramethyl-oct-4-ene-3,6-dione
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -78℃; | A 99% B 87% |
Conditions | Yield |
---|---|
In toluene solvent removing, crystals washing and drying; | A n/a B 99% |
pentaphenylphosphorus
triphenyl bismuth (2+); dichloride
triphenylbismuthane
Conditions | Yield |
---|---|
In toluene byproducts: tetraphenylphosphorus chloride; mixt. of Ph5P and Ph3BiCl2 in toluene heated at 100°C for 1 h in evacuated glass ampoule; cooling, removal of solvent, treatment with petroleum ether, evapn. of etheral extracts; | 98% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide byproducts: C6H5C(O)CHCH2; K-compd. addn. to Bi-compd. suspn. at -78°C, mixt. allowing to warm to room temp., solvent removal under reduced pressure, residue extn. (Et2O), extract evapn.; residue chromy. on silica gel (hexane, EtOAc 100:o to 80:20); | 98% |
triphenylbismuth difluoride
triphenylbismuthane
Conditions | Yield |
---|---|
In ethanol room temp., 1 h; | 98% |
In ethanol room temp., 1 h; | 98% |
sodium benzoate
methyltriphenylbismuthonium tetrafluoroborate
A
benzoic acid methyl ester
B
triphenylbismuthane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide mixt. (Ph3BiMe)(BF4), sodium benzoate, and DMF was stirred at room temp. for 2 h; water and Et2O was added and stirred, organic phase was separated and dried over MgSO4 and evapd.; | A 30% B 97% |
pentaphenylphosphorus
triphenylbismuth dibromide
triphenylbismuthane
Conditions | Yield |
---|---|
In toluene byproducts: tetraphenylphosphorus bromide; mixt. of Ph5P and Ph3BiBr2 in toluene heated at 100°C for 1 h in evacuated glass ampoule; cooling, removal of solvent, treatment with petroleum ether, evapn. of etheral extracts; | 96% |
pentaphenylphosphorus
triphenylbismuth(V) difluoride
triphenylbismuthane
Conditions | Yield |
---|---|
In toluene byproducts: tetraphenylphosphorus fluoride; mixt. of Ph5P and Ph3BiF2 in toluene heated at 100°C for 1 h in evacuated glass ampoule; cooling, removal of solvent, treatment with petroleum ether, evapn. of etheral extracts; | 96% |
pentaphenylbismuth
A
bromobenzene
B
triphenylbismuthane
C
tetraphenylantimony(V) bromide
Conditions | Yield |
---|---|
In toluene 0.5 h, 20°C; solvent and bromobenzene removing, crystals washing (petroleum ether) and drying, Ph4SbBr in residue, Ph3Bi in petroleum ether soln.; | A n/a B 96% C 86% |
3,5-Di-tert-butylphenol
4-nitrophenoxytetraphenylbismuth
A
4-nitrophenyl phenyl ether
B
triphenylbismuthane
Conditions | Yield |
---|---|
With 1,1-Diphenylethylene In toluene stirring mixt. in toluene for 5 h under Ar under reflux; removal of solvent, column chromy. of residue (hexane); | A 96% B 70% |
In toluene stirring mixt. in toluene for 5 h under Ar under reflux; removal of solvent, column chromy. of residue (hexane); | A 95% B 79% |
diphenylbismuth 4-methylbenzenesulfonate
pentaphenylantimony
A
tetraphenylantimony 4-methylbenzenesulfonate
B
triphenylbismuthane
Conditions | Yield |
---|---|
In diethyl ether mixt. of Ph5Sb and Bi sulfonate in ether kept for 48 h at 20°C; ppt. filtered, washed (hexane), dried; ethereal and hexane soln. evapd.,recrystd. from EtOH; | A 93% B 96% |
Conditions | Yield |
---|---|
With triethylamine; palladium diacetate In N,N,N,N,N,N-hexamethylphosphoric triamide at 65℃; for 0.166667h; | 100% |
With para-bromotoluene; C22H25ClNPPdS; potassium carbonate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere; Schlenk technique; | 48% |
With 2-thioxo-3H-1,3-benzothiazole; copper diacetate; bis(dibenzylideneacetone)-palladium(0) In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; | 19 %Chromat. |
N-ethylbenzimidazolinone
triphenylbismuthane
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In dichloromethane for 23h; Ambient temperature; | 100% |
triphenylbismuthane
2-azabicyclo[2.2.1.]hept-5-en-3-one
rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In dichloromethane for 24h; Ambient temperature; | 100% |
triphenylbismuthane
tri-tert-butyl hydrazine-1,1,2-tricarboxylate
1,1,2-tris(tert-butoxycarbonyl)-2-phenylhydrazine
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In dichloromethane at 20℃; for 23h; Arylation; | 100% |
triphenylbismuthane
tert-butyl 2-(4-nitrophenyl)diazenecarboxylate
Conditions | Yield |
---|---|
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h; | 100% |
tert-butyl 2-(4-methylphenyl)azocarboxylate
triphenylbismuthane
Conditions | Yield |
---|---|
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h; | 100% |
di-tert-butyl-diazodicarboxylate
triphenylbismuthane
di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate
Conditions | Yield |
---|---|
With copper diacetate; 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 75℃; for 0.25h; | 100% |
Conditions | Yield |
---|---|
byproducts: benzene; heating (CH3)3NHCl with triphenyl bismuth at 130°C (also in presence of ethanol);; | 100% |
byproducts: benzene; heating (CH3)3NHCl with triphenyl bismuth at 130°C (also in presence of ethanol);; | 100% |
Conditions | Yield |
---|---|
In diethyl ether byproducts: C6H5I; | 100% |
In diethyl ether byproducts: C6H5I; | 100% |
byproducts: C6H5I; |
bismuth(III) chloride
triphenylbismuthane
diphenylbismuth(III) chloride
Conditions | Yield |
---|---|
In diethyl ether 20°C; | 100% |
In diethyl ether 20°C; | 100% |
In toluene; xylene 30 min reflux; | 97% |
N,N,N,N,N,N-hexamethylphosphoric triamide
trimethylsilyl trifluoromethanesulfonate
triphenylbismuthane
Conditions | Yield |
---|---|
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.; | 100% |
1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione
triphenylbismuthane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: C6H6; Distn.; Evapn. in vac., vac. sublimation, elem. anal.; | 100% |
triphenylbismuthane
triphenylbismuth oxalate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; oxalic acid In diethyl ether byproducts: (CH3)3COH, H2O; molar ratio Bi(C6H5)3:C4H9OOH:acid = 1:1:1; stirred at room temp. for one day; liquid part distd. off at a reduced pressure, product recrystd. from ethyl acetate; elem. anal.; | 100% |
triphenylbismuthane
triphenylbismuth(V) diacetate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; acetic acid In diethyl ether byproducts: (CH3)3COH, H2O; molar ratio Bi(C6H5)3:(CH3)3COOH:CH3COOH = 1:1:2; stirred at room temp.for one day; liquid distd. off at a reduced pressure, product recrystd. from ethyl acetate, elem. anal.; | 100% |
Multi-step reaction with 2 steps 1: Chloramin T / acetonitrile 2: CH3COOH View Scheme | |
With ozone; ethyl acetate In ethyl acetate ethyl acetate satd. with ozone at -78°C; warmed to ambient temp.; BiPh3 added; soln. evapd. in vac.; quant. recovery of unchanged BiPh3; | 0% |
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