Triphenylbismuth supplier | CasNO.603-33-8

Name
Triphenylbismuth
EINECS 210-033-4
CAS No. 603-33-8
Article Data194
CAS DataBase
Density 1.585 g/cm³
Solubility insoluble in water
Melting Point 78-80 °C
Formula C₁₈H₁₅Bi
Boiling Point 310 °C
Molecular Weight 440.298
Flash Point 242 °C/14mm
Transport Information
Appearance white to off-white crystalline powder
Safety 24/25-36/37
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms NSC 465;Triphenylbismuthine;
PSA 0.00000
LogP 4.46040

Synthetic route

: 7787-58-8
bismuth(III) bromide

: 587-85-9
diphenylmercury(II)

: 603-33-8
triphenylbismuthane

Conditions

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

: BiO2SC6H5

: 603-33-8
triphenylbismuthane

Conditions

Conditions	Yield
In not given byproducts: SO2; 4h at 216°C under 1E-2 - 1E-3 Torr;	100%

: 28719-55-3, 7065-17-0
dibromotriphenylbismuth

: 603-33-8
triphenylbismuthane

Conditions

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;

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

: 603-33-8
triphenylbismuthane

Conditions

Conditions	Yield
In ethanol 1h reflux;	100%
in alkaline medium;
in alkaline medium;

: 28719-54-2, 507233-69-4, 594-30-9
triphenylbismuth dichloride

: 603-33-8
triphenylbismuthane

Conditions

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;

: 42967-53-3
tetraphenylbismuth chloride

A: 603-33-8
triphenylbismuthane

B: 108-90-7
chlorobenzene

Conditions

Conditions	Yield
In not given decomposition at room temp.;	A 100% B 100%

: C6H5Bi(O2SC6H5)2

: 603-33-8
triphenylbismuthane

Conditions

Conditions	Yield
In not given byproducts: SO2; 4h at 190°C under 1E-2 - 1E-3 Torr;	100%

: 3049-07-8
pentaphenylbismuth

: 603-33-8
triphenylbismuthane

Conditions

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%

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

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

A: 67-56-1
methanol

B: 115-10-6
Dimethyl ether

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

D: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

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

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 67-63-0
isopropyl alcohol

A: 598-53-8
isopropyl methyl ether

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

C: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

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

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 100-51-6
benzyl alcohol

A: 538-86-3
benzyl methyl ether

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

C: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 67-56-1
methanol

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

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

A: 115-10-6
Dimethyl ether

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

C: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

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

: 64-17-5
ethanol

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

A: 540-67-0
ethyl methyl ether

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

C: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 603-35-0
triphenylphosphine

A: triphenyl-methylphosphonium tetrafluoroborate

B: 603-33-8
triphenylbismuthane

Conditions

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

...Expand

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

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

A: 603-33-8
triphenylbismuthane

B: 1-methoxy-N,N-dimethylmethyleneiminium tetrafluoroborate

Conditions

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%

...Expand

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 603-32-7
triphenyl-arsane

A: 603-33-8
triphenylbismuthane

B: methyltriphenylarsonium tetrafluoroborate

Conditions

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

...Expand

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 603-36-1
triphenylantimony

A: 3802-09-3
methyltriphenylstibonium tetrafluoroborate

B: 603-33-8
triphenylbismuthane

Conditions

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

...Expand

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

: 62-55-5
thioacetamide

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

B: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 2-(isopropoxycarbonyl)ethyl(triphenyl)bismuthonium trifluoromethanesulfonate

: 603-33-8
triphenylbismuthane

Conditions

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

: 586-96-9
Nitrosobenzene

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

A: 603-33-8
triphenylbismuthane

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

Conditions

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

...Expand

: triphenlbismuth dibromide

: 3049-07-8
pentaphenylbismuth

A: 108-86-1
bromobenzene

B: 603-33-8
triphenylbismuthane

Conditions

Conditions	Yield
In toluene solvent removing, crystals washing and drying;	A n/a B 99%

...Expand

: 2588-88-7
pentaphenylphosphorus

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

: 603-33-8
triphenylbismuthane

Conditions

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%

: 865-47-4
potassium tert-butylate

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

: 603-33-8
triphenylbismuthane

Conditions

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%

: hydrazinium hydroxide

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

: 603-33-8
triphenylbismuthane

Conditions

Conditions	Yield
In ethanol room temp., 1 h;	98%
In ethanol room temp., 1 h;	98%

: 532-32-1
sodium benzoate

: 278172-59-1
methyltriphenylbismuthonium tetrafluoroborate

A: 93-58-3
benzoic acid methyl ester

B: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 2588-88-7
pentaphenylphosphorus

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

: 603-33-8
triphenylbismuthane

Conditions

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%

: 2588-88-7
pentaphenylphosphorus

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

: 603-33-8
triphenylbismuthane

Conditions

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%

: triphenylantmony dibromide

: 3049-07-8
pentaphenylbismuth

A: 108-86-1
bromobenzene

B: 603-33-8
triphenylbismuthane

C: 16894-69-2
tetraphenylantimony(V) bromide

Conditions

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%

...Expand

: 1138-52-9
3,5-Di-tert-butylphenol

: 105071-86-1
4-nitrophenoxytetraphenylbismuth

A: 620-88-2
4-nitrophenyl phenyl ether

B: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 108858-14-6
diphenylbismuth 4-methylbenzenesulfonate

: 2170-05-0
pentaphenylantimony

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

B: 603-33-8
triphenylbismuthane

Conditions

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%

...Expand

: 603-33-8
triphenylbismuthane

: 92-52-4
biphenyl

Conditions

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.

: 10045-45-1
N-ethylbenzimidazolinone

: 603-33-8
triphenylbismuthane

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane for 23h; Ambient temperature;	100%

: 603-33-8
triphenylbismuthane

: 49805-30-3
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

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane for 24h; Ambient temperature;	100%

: 603-33-8
triphenylbismuthane

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

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 20℃; for 23h; Arylation;	100%

: 603-33-8
triphenylbismuthane

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

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

Conditions

Conditions	Yield
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h;	100%

: 773893-07-5
tert-butyl 2-(4-methylphenyl)azocarboxylate

: 603-33-8
triphenylbismuthane

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

Conditions

Conditions	Yield
With methanol; copper diacetate In acetonitrile at 70℃; for 0.0833333h;	100%

: 870-50-8
di-tert-butyl-diazodicarboxylate

: 603-33-8
triphenylbismuthane

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

Conditions

Conditions	Yield
With copper diacetate; 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 75℃; for 0.25h;	100%

: 593-81-7
trimethylamine hydrochloride

: 603-33-8
triphenylbismuthane

: 7787-60-2
bismuth(III) chloride

Conditions

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%

: 7790-99-0
Iodine monochloride

: 603-33-8
triphenylbismuthane

: 5153-28-6
diphenylbismuth(III) chloride

Conditions

Conditions	Yield
In diethyl ether byproducts: C6H5I;	100%
In diethyl ether byproducts: C6H5I;	100%
byproducts: C6H5I;

: 7787-60-2
bismuth(III) chloride

: 603-33-8
triphenylbismuthane

: 5153-28-6
diphenylbismuth(III) chloride

Conditions

Conditions	Yield
In diethyl ether 20°C;	100%
In diethyl ether 20°C;	100%
In toluene; xylene 30 min reflux;	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 603-33-8
triphenylbismuthane

: diphenylbismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

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%

...Expand

: 22767-90-4
1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione

: 603-33-8
triphenylbismuthane

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

Conditions

Conditions	Yield
In neat (no solvent) byproducts: C6H6; Distn.; Evapn. in vac., vac. sublimation, elem. anal.;	100%

: 603-33-8
triphenylbismuthane

: 97068-77-4
triphenylbismuth oxalate

Conditions

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%

: 603-33-8
triphenylbismuthane

: 28899-97-0
triphenylbismuth(V) diacetate

Conditions

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%

Triphenylbismuth Consensus Reports

Reported in EPA TSCA Inventory.

Triphenylbismuth Standards and Recommendations

PURITY: 98.0% min
Bi CONTENT: 47.0 - 48.0%
METALLIC IMPURITY: 0.1% max

Triphenylbismuth Specification

The Triphenylbismuthine, with its CAS registry number 603-33-8, is a kind of white to off-white crystalline powder. For being sensitive to moisture and insoluble in water, its product categories are including blocks; BuildingBlocks; Organometallics.

The physical properties of this chemical are as below: (1)#H bond acceptors: 0 ; (2)#H bond donors: 0 ; (3)#Freely Rotating Bonds: 3 ; (4)Polar Surface Area: 0; (5)Exact Mass: 440.097758; (6)MonoIsotopic Mass: 440.097758; (7)Heavy Atom Count: 19; (8)Complexity: 202; (9)Covalently-Bonded Unit Count: 1.

Use of this chemical is below: Triphenylbismuthine could react with piperidine to produce 1-phenyl-piperidine with the catalytic agent of Cu(OAc)₂ and the solvent of CH₂Cl₂. And in this reaction, the reaction time is 18 hour(s) and the yield is 56 % in the ambient temperature.

When you are dealing with this chemical, you should be careful. For being a kind of harmful chemical which may cause damage to health, it is dangerous to our body if by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing and gloves and then avoid contact with skin and eyes.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3
(2)InChI: InChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H;
(3)InChIKey: ZHXAZZQXWJJBHA-UHFFFAOYSA-N

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)	U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01712,
mouse	LDLo	intraperitoneal	250mg/kg (250mg/kg)	"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 317, 1952.
mouse	LDLo	oral	320mg/kg (320mg/kg)	Archives of Environmental Contamination and Toxicology. Vol. 14, Pg. 111, 1985.

Product Name

Triphenylbismuth

Synthetic route

Triphenylbismuth Consensus Reports

Triphenylbismuth Standards and Recommendations

Triphenylbismuth Specification

Related Products

Hot Products