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603-33-8

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  • Triphenylbismuth CAS 603-33-8 Bismuthine, triphenyl- CAS no 603-33-8 BISMUTH TRIPHENYL TRIPHENYLBISMUTHINE

    Cas No: 603-33-8

  • USD $ 3.5-5.0 / Kiloliter

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603-33-8 Usage

Chemical Properties

white to off-white crystalline powder

Uses

Triphenylbismuth, as an volatile organometallic used in the preparation of thin films of superconducting oxides by CVD. It is also added to the fuel of rocket as cruing agent. It acts as a solidifying catalyst for butyl hydroxyl propellants.

Purification Methods

Dissolve it in EtOH, precipitate it with H2O, extract with Et2O, dry and evaporate till the residue crystallises. It has been recrystallised from EtOH and Et2O/EtOH and is a stable compound. [Forward et al. J Chem Soc suppl p121 1949, Pfeiffer et al. Chem Ber 37 4620 1904, Gilman & Yablunky J Am Chem Soc 62 665 1940, UV: Jaffé J Chem Phys 22 1430 1954, Beilstein 4 III 1841.]

Check Digit Verification of cas no

The CAS Registry Mumber 603-33-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 603-33:
(5*6)+(4*0)+(3*3)+(2*3)+(1*3)=48
48 % 10 = 8
So 603-33-8 is a valid CAS Registry Number.
InChI:InChI=1/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H;/rC18H15Bi/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

603-33-8 Well-known Company Product Price

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  • Alfa Aesar

  • (12545)  Triphenylbismuth, 99+%   

  • 603-33-8

  • 5g

  • 153.0CNY

  • Detail
  • Alfa Aesar

  • (12545)  Triphenylbismuth, 99+%   

  • 603-33-8

  • 25g

  • 769.0CNY

  • Detail
  • Alfa Aesar

  • (12545)  Triphenylbismuth, 99+%   

  • 603-33-8

  • 100g

  • 3078.0CNY

  • Detail

603-33-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Triphenylbismuth

1.2 Other means of identification

Product number -
Other names Bismuthine, triphenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:603-33-8 SDS

603-33-8Synthetic route

bismuth(III) bromide
7787-58-8

bismuth(III) bromide

diphenylmercury(II)
587-85-9

diphenylmercury(II)

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In diethyl ether byproducts: C6H5HgBr; 12h; distillation of ether phase;100%
BiO2SC6H5

BiO2SC6H5

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In not given byproducts: SO2; 4h at 216°C under 1E-2 - 1E-3 Torr;100%
dibromotriphenylbismuth
28719-55-3, 7065-17-0

dibromotriphenylbismuth

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
2023-48-5, 28719-53-1

triphenylbismuth difluoride

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In ethanol 1h reflux;100%
in alkaline medium;
in alkaline medium;
triphenylbismuth dichloride
28719-54-2, 507233-69-4, 594-30-9

triphenylbismuth dichloride

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In ethanol 1h reflux;100%
With sodium hydrogensulfite In acetone at 0°C;80%
With potassium hydroxide In ethanol 5h reflux or shaking;
tetraphenylbismuth chloride
42967-53-3

tetraphenylbismuth chloride

A

triphenylbismuthane
603-33-8

triphenylbismuthane

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
In not given decomposition at room temp.;A 100%
B 100%
C6H5Bi(O2SC6H5)2

C6H5Bi(O2SC6H5)2

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In not given byproducts: SO2; 4h at 190°C under 1E-2 - 1E-3 Torr;100%
pentaphenylbismuth
3049-07-8

pentaphenylbismuth

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

A

methanol
67-56-1

methanol

B

Dimethyl ether
115-10-6

Dimethyl ether

C

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

D

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

isopropyl alcohol
67-63-0

isopropyl alcohol

A

isopropyl methyl ether
598-53-8

isopropyl methyl ether

B

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

C

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

benzyl alcohol
100-51-6

benzyl alcohol

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

C

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
67-56-1

methanol

2,6-di-tert-butyl-4-methylpyridine
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

A

Dimethyl ether
115-10-6

Dimethyl ether

B

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

C

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

ethanol
64-17-5

ethanol

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

A

ethyl methyl ether
540-67-0

ethyl methyl ether

B

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

C

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

triphenylphosphine
603-35-0

triphenylphosphine

A

triphenyl-methylphosphonium tetrafluoroborate

triphenyl-methylphosphonium tetrafluoroborate

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In chloroform-d1 react. (Ph3BiMe)(BF4) and PPh3 in CDCl3 at room temp.; detn. by 1H NMR;A 100%
B 100%
methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

triphenylbismuthane
603-33-8

triphenylbismuthane

B

1-methoxy-N,N-dimethylmethyleneiminium tetrafluoroborate

1-methoxy-N,N-dimethylmethyleneiminium tetrafluoroborate

Conditions
ConditionsYield
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
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

triphenyl-arsane
603-32-7

triphenyl-arsane

A

triphenylbismuthane
603-33-8

triphenylbismuthane

B

methyltriphenylarsonium tetrafluoroborate

methyltriphenylarsonium tetrafluoroborate

Conditions
ConditionsYield
In chloroform-d1 react. (Ph3BiMe)(BF4) and AsPh3 in CDCl3 at room temp.; detn. by 1H NMR;A 100%
B 100%
methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

triphenylantimony
603-36-1

triphenylantimony

A

methyltriphenylstibonium tetrafluoroborate
3802-09-3

methyltriphenylstibonium tetrafluoroborate

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In chloroform-d1 react. (Ph3BiMe)(BF4) and SbPh3 in CDCl3 at room temp.; detn. by 1H NMR;A 100%
B 100%
methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

thioacetamide
62-55-5

thioacetamide

A

1-(methylthio)ethyleneiminium tetrafluoroborate
277306-39-5

1-(methylthio)ethyleneiminium tetrafluoroborate

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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%
2-(isopropoxycarbonyl)ethyl(triphenyl)bismuthonium trifluoromethanesulfonate

2-(isopropoxycarbonyl)ethyl(triphenyl)bismuthonium trifluoromethanesulfonate

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In chloroform-d1 Kinetics; byproducts: i-PrOC(O)C2H4OSO2CF3; sample soln. decompn. at 25°C; (1)H-NMR monitoring;100%
Nitrosobenzene
586-96-9

Nitrosobenzene

(3,3-dimethyl-2-oxobutyl)triphenylbismuthonium tetrafluoroborate

(3,3-dimethyl-2-oxobutyl)triphenylbismuthonium tetrafluoroborate

A

triphenylbismuthane
603-33-8

triphenylbismuthane

B

(E)-2,2,7,7-Tetramethyl-oct-4-ene-3,6-dione
10507-31-0

(E)-2,2,7,7-Tetramethyl-oct-4-ene-3,6-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -78℃;A 99%
B 87%
triphenlbismuth dibromide

triphenlbismuth dibromide

pentaphenylbismuth
3049-07-8

pentaphenylbismuth

A

bromobenzene
108-86-1

bromobenzene

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In toluene solvent removing, crystals washing and drying;A n/a
B 99%
pentaphenylphosphorus
2588-88-7

pentaphenylphosphorus

triphenyl bismuth (2+); dichloride
507233-69-4, 594-30-9, 28719-54-2

triphenyl bismuth (2+); dichloride

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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%
potassium tert-butylate
865-47-4

potassium tert-butylate

3-oxo-3-phenylpropyl(triphenyl)bismuthonium tetrafluoroborate

3-oxo-3-phenylpropyl(triphenyl)bismuthonium tetrafluoroborate

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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%
hydrazinium hydroxide

hydrazinium hydroxide

triphenylbismuth difluoride
2023-48-5, 28719-53-1

triphenylbismuth difluoride

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In ethanol room temp., 1 h;98%
In ethanol room temp., 1 h;98%
sodium benzoate
532-32-1

sodium benzoate

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
2588-88-7

pentaphenylphosphorus

triphenylbismuth dibromide
28719-55-3, 7065-17-0

triphenylbismuth dibromide

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
2588-88-7

pentaphenylphosphorus

triphenylbismuth(V) difluoride
2023-48-5, 28719-53-1

triphenylbismuth(V) difluoride

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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%
triphenylantmony dibromide

triphenylantmony dibromide

pentaphenylbismuth
3049-07-8

pentaphenylbismuth

A

bromobenzene
108-86-1

bromobenzene

B

triphenylbismuthane
603-33-8

triphenylbismuthane

C

tetraphenylantimony(V) bromide
16894-69-2

tetraphenylantimony(V) bromide

Conditions
ConditionsYield
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
1138-52-9

3,5-Di-tert-butylphenol

4-nitrophenoxytetraphenylbismuth
105071-86-1

4-nitrophenoxytetraphenylbismuth

A

4-nitrophenyl phenyl ether
620-88-2

4-nitrophenyl phenyl ether

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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
108858-14-6

diphenylbismuth 4-methylbenzenesulfonate

pentaphenylantimony
2170-05-0

pentaphenylantimony

A

tetraphenylantimony 4-methylbenzenesulfonate
104316-53-2, 481073-75-0

tetraphenylantimony 4-methylbenzenesulfonate

B

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
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%
triphenylbismuthane
603-33-8

triphenylbismuthane

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
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
10045-45-1

N-ethylbenzimidazolinone

triphenylbismuthane
603-33-8

triphenylbismuthane

1-ethyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

1-ethyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane for 23h; Ambient temperature;100%
triphenylbismuthane
603-33-8

triphenylbismuthane

2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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
186586-76-5

rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane for 24h; Ambient temperature;100%
triphenylbismuthane
603-33-8

triphenylbismuthane

tri-tert-butyl hydrazine-1,1,2-tricarboxylate
185456-26-2

tri-tert-butyl hydrazine-1,1,2-tricarboxylate

1,1,2-tris(tert-butoxycarbonyl)-2-phenylhydrazine
312934-60-4

1,1,2-tris(tert-butoxycarbonyl)-2-phenylhydrazine

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane at 20℃; for 23h; Arylation;100%
triphenylbismuthane
603-33-8

triphenylbismuthane

tert-butyl 2-(4-nitrophenyl)diazenecarboxylate
92722-14-0

tert-butyl 2-(4-nitrophenyl)diazenecarboxylate

tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate

tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate

Conditions
ConditionsYield
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h;100%
tert-butyl 2-(4-methylphenyl)azocarboxylate
773893-07-5

tert-butyl 2-(4-methylphenyl)azocarboxylate

triphenylbismuthane
603-33-8

triphenylbismuthane

N'-phenyl-N'-p-tolyl-hydrazinecarboxylic acid tert-butyl ester

N'-phenyl-N'-p-tolyl-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h;100%
di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

triphenylbismuthane
603-33-8

triphenylbismuthane

di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate
65578-58-7

di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With copper diacetate; 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 75℃; for 0.25h;100%
trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

triphenylbismuthane
603-33-8

triphenylbismuthane

bismuth(III) chloride
7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
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%
Iodine monochloride
7790-99-0

Iodine monochloride

triphenylbismuthane
603-33-8

triphenylbismuthane

diphenylbismuth(III) chloride
5153-28-6

diphenylbismuth(III) chloride

Conditions
ConditionsYield
In diethyl ether byproducts: C6H5I;100%
In diethyl ether byproducts: C6H5I;100%
byproducts: C6H5I;
bismuth(III) chloride
7787-60-2

bismuth(III) chloride

triphenylbismuthane
603-33-8

triphenylbismuthane

diphenylbismuth(III) chloride
5153-28-6

diphenylbismuth(III) chloride

Conditions
ConditionsYield
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
680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

triphenylbismuthane
603-33-8

triphenylbismuthane

diphenylbismuth triflate - (hexamethylphosphoric triamide)2 complex

diphenylbismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions
ConditionsYield
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
22767-90-4

1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione

triphenylbismuthane
603-33-8

triphenylbismuthane

Bi(3+)*3F3CCOCHCOC(CH3)3(1-)=Bi(F3CCOCHCOC(CH3)3)3

Bi(3+)*3F3CCOCHCOC(CH3)3(1-)=Bi(F3CCOCHCOC(CH3)3)3

Conditions
ConditionsYield
In neat (no solvent) byproducts: C6H6; Distn.; Evapn. in vac., vac. sublimation, elem. anal.;100%
triphenylbismuthane
603-33-8

triphenylbismuthane

triphenylbismuth oxalate
97068-77-4

triphenylbismuth oxalate

Conditions
ConditionsYield
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
603-33-8

triphenylbismuthane

triphenylbismuth(V) diacetate
28899-97-0

triphenylbismuth(V) diacetate

Conditions
ConditionsYield
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%

603-33-8Relevant articles and documents

Phenylbismuth bis(2,5-dimethylbenzenesulfonate): Structure and properties

Sharutin,Sharutina

, p. 1119 - 1122 (2014)

Phenylbismuth bis(2,5-dimethylbenzenesulfonate) (I), a coordination polymer in which a bis-muth atom has a distorted square pyramidal coordination to an axial carbon atom (Bi-C, 2.247(5) A?) and basal oxygen atoms (Bi-O, 2.390(9)-2.403(10) A?), has been synthesized by the reaction between triphenyl- bismuth and 2,5-dimethylbenzenesulfonic acid (1 : 2 mol/mol) in toluene and structurally characterized. Pentaphenylbismuth and pentaphenylantimony phenylate compound I to triphenylbismuth.

Challenger, F.,Peters, A. T.,Halevy, J.

, (1926)

Reactivity of TerN(SiMe3)BiCl2 - Synthesis of an Aminobismuthenium Cation and TerN(SiMe3)Bi(N3)2

Bresien, Jonas,Hering-Junghans, Christian,Schulz, Axel,Thomas, Max,Villinger, Alexander

, p. 2571 - 2580 (2018)

The reaction of TerN(SiMe3)BiCl2 (1) (Ter = 2,6-bis(2,4,6-trimethylphenyl)phenyl) with Lewis acids such as GaCl3 and Ag[OTf] (OTf = OSO2CF3) was studied. While the reaction of 1 with GaCl3 led to decomposition into bismuth black, TerNH2·GaCl3, and [TerNH3][GaCl4], the reactions of 1 with 1 and 2 equiv of Ag[OTf] resulted in methyl/triflate exchange reactions affording TerN(SiMe2OTf)Bi(Me)Cl (2) and TerN(SiMe2OTf)Bi(Me)OTf (3). To circumvent the methyl/triflate exchange, the diiodide compound TerN(SiMe3)BiI2 (5) and the azide-substituted derivatives TerN(SiMe3)Bi(Cl)N3 (6) and TerN(SiMe3)Bi(N3)2 (7) were prepared, although it was not possible to isolate pure 7 because of small impurities of 6. All of the bismuth compounds (1-7) were characterized by single-crystal X-ray diffraction and NMR, IR, and Raman spectroscopy. According to quantum-chemical calculations, 3 can be regarded as a donor-stabilized aminobismuthenium cation with OTf- as the counterion. As expected for bismuth compounds with aromatic scaffolds, Bi···-arene interactions were observed. The influence of the substitution at the bismuth atom on the strength of this intramolecular interaction with the terphenyl moiety was studied by experimental (crystal structures) and theoretical methods. A correlation between the Lewis acidity (NBO charge) and the Bi···-arene distance could be established.

Zinc reaction with diphenylantimony and diphenylbismuth chlorides in aprotic solvents

Losev,Klement'eva,Maslennikov,Spirina

, p. 1581 - 1583 (2006)

Products of zinc oxidation with diphenylantimony and diphenylbismuth chlorides in aprotic solvents are established. The effective adsorption constants of the reagents on the metal surface and the rate constants and activation energies of the processes und

The Importance of Heterolepticity in Improving the Antibacterial Activity of Bismuth(III) Thiolates

Luqman, Ahmad,Blair, Victoria L.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.,Andrews, Philip C.

, p. 2738 - 2749 (2016)

Five mixed thiolatobismuth(III) complexes [BiPh(5-MMTD)2{4-MMT(H)}] (1), [Bi(1-MMTZ)2{(PYM)(PYM(H))2}] (2), [Bi(MBT)2(5-MMTD)] (3), [Bi(4-BrMTD)3{2-MMI(H)}] (4) and [Bi(1-MMTZ)2{1-MMTZ(H)}(

Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

Luqman, Ahmad,Blair, Victoria L.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.,Kedzierski, Lukasz,Andrews, Philip C.

, p. 725 - 733 (2015)

Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)2]2 and [Bi(MBT)3]2. Syntheses were achieved using BiPh3 or Bi(OtBu)3 in protolysis reactions with MBT(H), or by salt metathesis with BiCl3 or BiPhCl2 and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)2]2 and [Bi(MBT)3]2, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)2]2 to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)3]2 was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)3], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)2]2 also was found to display good antileishmanial activity with an IC50 value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.

METHOD FOR PREPARING HETEROLEPTIC TRIARYLBISMUTHANES AND COMPOUNDS PRODUCED BY THE SAME

-

Paragraph 0070, (2021/05/21)

A method for controlling dismutation in the synthesis of a heteroleptic triarylbismuthane is provided as are compounds produced by such a method and use of the same to inhibit the replication of microorganisms.

Investigation into the Organobismuth Dismutation and Its Use for Rational Synthesis of Heteroleptic Triarylbismuthanes, Ar12Ar2Bi

Hyvl, Jakub,Louis-Goff, Thomas,Rheingold, Arnold L.

supporting information, (2020/03/16)

Organobismuthanes undergo dismutation, a substituent scrambling process, complicating the synthesis of unsymmetrically trisubstituted bismuthanes of the general formula Ar12Ar2Bi. Although the dismutation is a mechanistically diverse phenomenon, at ambient or lower temperatures, dismutation is triggered mainly by an electrophilic bismuth source. Therefore, the selection of the electrophile, Ar12BiX (X = tosylate or iodide if Ar1 = mesityl) or Ar1BiX2 (X = tosylate), and its use in low concentration during the reaction is key to suppressing the dismutation, leading to new, streamlined protocols utilizing direct arylations of Ar12BiX (X = OTs or I) or Ar1Bi(OTs)2 with organozincs affording heteroleptic triarylbismuthanes Ar12Ar2Bi.

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