Triphenylbismuth CAS#: 603-33-8; ChemWhat Code: 33629

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameTriphenylbismuth
IUPAC Nametriphenylbismuthane
Molecular StructureTriphenylbismuth-CAS-603-33-8
CAS Registry Number 603-33-8
EINECS Number210-033-4
MDL NumberMFCD00014064
SynonymsTPB, triphenylbismuthane, triphenylbismuthine, tris(phenyl)bismuthane, triphenylbismuth(III), Triphenylbismuthane, triphenyl bismuthin, triphenylbismuthin
Molecular FormulaC18H15Bi
Molecular Weight440.298
InChIInChI=1S/3C6H5.Bi/c3*1-2-4-6-5-3-1;/h3*1-5H;
InChI KeyZHXAZZQXWJJBHA-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3
Patent Information
Patent IDTitlePublication Date
US2015/112104Process For Producing Chlorinated Hydrocarbons In The Presence Of A Polyvalent Bismuth Compound2015
EP2133357LIVING RADICAL POLYMERIZATION PROMOTER2009
US2006/148842Nepetalactams and N-substituted derivatives thereof2006
US4225517Process for the production of acetaldehyde by the reaction of methanol with synthesis gas1980
US4364872Method of making aluminum alkyls1982

Physical Data

AppearanceOff-white to white crystal
Water SolubilityInsoluble
Flash Point242°C/14mm
SensitivityMoisture Sensitive
Melting Point, °C Solvent (Melting Point)
76diethyl ether
79neat (no solvent)
77-78petroleum ether
77 – 78methanol, ethanol
Boiling Point, °CPressure (Boiling Point), Torr
2080.07
24214
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C
1.5736 – 1.6427498.5 – 155
1.715475
1.585120
Description (Adsorption (MCS))Partner (Adsorption (MCS))
Adsorption to title compound DMF
Adsorption to title compound DMOS
Adsorption to title compound propylene carbonate
Adsorption to title compound acetonitrile
Adsorption to title compound methanol
Adsorption to title compound N-methylformamide
Adsorption to title compound formamide
Description (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Stability constant of the complex with24.9LiC6H5*O(C2H5)2

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Spectrum1Hchloroform-d120
Chemical shifts, Spectrum1Hdichloromethane-d226.84250.1
Chemical shifts, Spectrum13Cdichloromethane-d225.0462.9
Chemical shifts13Cchloroform-d1125
Triphenylbismuth CAS#: 603-33-8 HNMRTriphenylbismuth CAS 603-33-8 HNMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
Bandsgaseous matrix30-400
SpectrumKBr30
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)
Band assignmentnot given251 nm – 282 nm
Spectrum, Band assignmentfurther solvent(s)300 nm – 500 nm
Spectrumethanol200 – 300 nm

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Triphenylbismuth CAS 603-33-8
Route of Synthesis (ROS) of Triphenylbismuth CAS 603-33-8
ConditionsYield
Stage #1: bromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Reflux;
Stage #2: bismuth(III) chloride In tetrahydrofuran at -10 – 65℃; for 1.5h; Inert atmosphere;
83%
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 20 – 70℃; Cooling with ice; Inert atmosphere; Schlenk technique;
Stage #2: bismuth(III) chloride In tetrahydrofuran at 0 – 20℃; Inert atmosphere; Schlenk technique;

Experimental Procedure
General procedure: In a typical experiment, 0.5mmol of nitroarene and 0.002g(2mol%) NiNPs/DNA were added to 2mL water and thenstirred for 2-3min for thoroughly mixing. Subsequently,1mmol of NaBH4was added to the reaction mixture undermagnetic stirring at room temperature. The extent of thereaction was monitored by thin layer chromatography.Reproducibility of the results was checked by repeating theruns at least three times and was found to be within acceptablelimits (± 3%). When the reaction was completed, thereaction mixture was diluted with ethyl acetate and the catalystwas recovered by centrifugation. The combined organicfractions were dried over Na2SO4and evaporated underreduced pressure. The crude product was purified by columnchromatography on silica gel with a mixture of ethyl acetateand n-hexane as the eluent, and the ratio of ethyl acetate andn-hexane was depended on the structure of the products.The structure of isolated products was verified by 1H NMR.
82%
Stage #1: bromobenzene With magnesium In acetone; benzene for 1h; Reflux; Inert atmosphere;
Stage #2: bismuth(III) chloride In acetone; benzene for 4.5h; Reflux; Inert atmosphere;
68.2%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalDanger
GHS Hazard StatementsH302: Harmful if swallowed [Warning Acute toxicity, oral]
H312: Harmful in contact with skin [Warning Acute toxicity, dermal]
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]
Information may vary between notifications depending on impurities, additives, and other factors. 
Precautionary Statement CodesP261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNot dangerouse goods
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD 750/kg
Use Pattern
Triphenylbismuth CAS#: 603-33-8 is added to the fuel of rocket as cruing agent.

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Warshel Chemical Ltdhttp://www.warshel.com/
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