Triphenylbismuth

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  • Identifiers

    CAS number
    603-33-8

    Molecular formula
    C18H15Bi

    SMILES
    C1=CC=C(C=C1)[Bi](C2=CC=CC=C2)C3=CC=CC=C3

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 75.53%
    Rose 66.55%
    Green 55.69%
    Geranium 45.81%
    Metallic 45.02%
    Sweet 39.89%
    Honey 33.86%
    Fruity 33.18%
    Earthy 31.14%
    Leafy 29.11%

     

    Flavor
    Green 35.29%
    Rose 32.26%
    Geranium 23.84%
    Waxy 20.72%
    Tar 20.67%
    Floral 20.34%
    Tarry 20.18%
    Honey 20.11%
    Bitter 20.01%
    Moth ball 19.81%

     

  • Properties

    pKa est.
    5.04 (weak acid)

    Molecular weight
    440.3 g/mol

    Flash point

    • 184.63 ˚C est.

  • Synonyms

    • Triphenylbismuth
    • 603-33-8
    • Triphenylbismuthine
    • Triphenyl bismuth
    • BISMUTHINE, TRIPHENYL-
    • Aerotex
    • Trifenylbismutin
    • Triphenyl bismuthine
    • DTXSID6042498
    • NSC-465
    • R18732F41W
    • DTXCID4022498
    • Ph3Bi
    • RefChem:191900
    • 210-033-4
    • triphenylbismuthane
    • Bismuth triphenyl
    • Bismuth, triphenyl-
    • MFCD00014064
    • Caswell No. 896
    • Trifenylbismutin [Czech]
    • NSC 465
    • EINECS 210-033-4
    • EPA Pesticide Chemical Code 082801
    • BRN 3905930
    • AI3-51412
    • triphenylbismuthin
    • UNII-R18732F41W
    • triphenyl-bismuthin
    • triphenyl bismuthane
    • Triphenyl bismuth 97.5%
    • WLN: R-BI-R&R
    • TRIPHENYLBISMUTH [MI]
    • 4-16-00-01226 (Beilstein Handbook Reference)
    • SCHEMBL219794
    • (C6H5)3Bi
    • NSC465
    • orb1306748
    • Tox21_302240
    • AKOS015840405
    • AC-4365
    • NCGC00255966-01
    • CAS-603-33-8
    • FT145928
    • SY017812
    • DB-030494
    • HY-124076
    • CS-0084105
    • NS00080369
    • T0511
    • 603T338
    • A832697
    • Q4463253
    • Triphenylbismuth, 98% (99.9% trace metals basis)
    • 603-33-8

  • Applications

    Triphenylbismuth (CAS 603-33-8) is primarily used as an aryl-transfer reagent in organic synthesis, enabling C–C bond formation in cross-coupling and related arylation processes via transmetallation to transition-metal catalysts such as copper or palladium. It also serves as a precursor to other organobismuth species and a source of phenyl groups for radical or photochemical arylations under mild conditions. In research contexts, it is frequently evaluated as a less-toxic alternative to organotin reagents in aryl transfer chemistry. Additionally, triphenylbismuth appears in materials-related applications as a reactive intermediate in the synthesis of specialty polymers and coatings where controlled arylation steps are required, and thus is relevant to advanced materials development, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 10.84
    methanol 5.04
    isopropanol 8.92
    water 0.02
    ethyl acetate 41.09
    n-propanol 14.51
    acetone 49.78
    n-butanol 13.6
    acetonitrile 11.43
    DMF 132.03
    toluene 52.77
    isobutanol 11.28
    1,4-dioxane 140.16
    methyl acetate 38.04
    THF 407.84
    2-butanone 57.05
    n-pentanol 13.66
    sec-butanol 12.11
    n-hexane 5.27
    ethylene glycol 2.84
    NMP 213.46
    cyclohexane 15.3
    DMSO 88.52
    n-butyl acetate 57.65
    n-octanol 18.9
    chloroform 152.98
    n-propyl acetate 42.25
    acetic acid 15.57
    dichloromethane 132.75
    cyclohexanone 144.21
    propylene glycol 5.62
    isopropyl acetate 40.24
    DMAc 127.49
    2-ethoxyethanol 28.63
    isopentanol 13.28
    n-heptane 15.75
    ethyl formate 28.58
    1,2-dichloroethane 86.42
    n-hexanol 23.63
    2-methoxyethanol 33.97
    isobutyl acetate 38.5
    tetrachloromethane 22.91
    n-pentyl acetate 50.6
    transcutol 65.06
    n-heptanol 18.35
    ethylbenzene 32.54
    MIBK 44.94
    2-propoxyethanol 48.76
    tert-butanol 13.82
    MTBE 30.3
    2-butoxyethanol 32.69
    propionic acid 15.93
    o-xylene 34.7
    formic acid 3.53
    diethyl ether 37.0
    m-xylene 34.99
    p-xylene 30.94
    chlorobenzene 62.11
    dimethyl carbonate 39.81
    n-octane 8.86
    formamide 11.33
    cyclopentanone 262.83
    2-pentanone 56.64
    anisole 67.06
    cyclopentyl methyl ether 136.77
    gamma-butyrolactone 216.63
    1-methoxy-2-propanol 32.1
    pyridine 115.09
    3-pentanone 56.95
    furfural 156.35
    n-dodecane 6.06
    diethylene glycol 22.67
    diisopropyl ether 21.01
    tert-amyl alcohol 15.93
    acetylacetone 86.47
    n-hexadecane 7.13
    acetophenone 69.22
    methyl propionate 47.06
    isopentyl acetate 57.06
    trichloroethylene 192.63
    n-nonanol 21.46
    cyclohexanol 27.56
    benzyl alcohol 35.52
    2-ethylhexanol 28.18
    isooctanol 17.66
    dipropyl ether 61.97
    1,2-dichlorobenzene 67.8
    ethyl lactate 22.5
    propylene carbonate 103.07
    n-methylformamide 31.58
    2-pentanol 12.81
    n-pentane 5.71
    1-propoxy-2-propanol 44.77
    1-methoxy-2-propyl acetate 79.07
    2-(2-methoxypropoxy) propanol 38.29
    mesitylene 23.82
    ε-caprolactone 115.86
    p-cymene 34.66
    epichlorohydrin 220.9
    1,1,1-trichloroethane 76.85
    2-aminoethanol 6.89
    morpholine-4-carbaldehyde 169.47
    sulfolane 259.65
    2,2,4-trimethylpentane 5.35
    2-methyltetrahydrofuran 162.72
    n-hexyl acetate 51.04
    isooctane 4.08
    2-(2-butoxyethoxy)ethanol 43.49
    sec-butyl acetate 37.42
    tert-butyl acetate 56.64
    decalin 10.95
    glycerin 9.87
    diglyme 96.91
    acrylic acid 17.69
    isopropyl myristate 31.51
    n-butyric acid 26.15
    acetyl acetate 35.58
    di(2-ethylhexyl) phthalate 28.94
    ethyl propionate 41.93
    nitromethane 44.09
    1,2-diethoxyethane 61.62
    benzonitrile 49.33
    trioctyl phosphate 23.0
    1-bromopropane 48.86
    gamma-valerolactone 247.58
    n-decanol 17.34
    triethyl phosphate 36.29
    4-methyl-2-pentanol 11.51
    propionitrile 17.84
    vinylene carbonate 84.62
    1,1,2-trichlorotrifluoroethane 104.0
    DMS 50.84
    cumene 23.56
    2-octanol 16.28
    2-hexanone 50.06
    octyl acetate 34.66
    limonene 49.49
    1,2-dimethoxyethane 79.13
    ethyl orthosilicate 36.33
    tributyl phosphate 26.14
    diacetone alcohol 47.13
    N,N-dimethylaniline 52.17
    acrylonitrile 23.84
    aniline 40.0
    1,3-propanediol 11.29
    bromobenzene 74.69
    dibromomethane 88.17
    1,1,2,2-tetrachloroethane 148.98
    2-methyl-cyclohexyl acetate 60.65
    tetrabutyl urea 41.05
    diisobutyl methanol 24.17
    2-phenylethanol 44.92
    styrene 37.92
    dioctyl adipate 42.94
    dimethyl sulfate 85.87
    ethyl butyrate 57.36
    methyl lactate 24.69
    butyl lactate 32.6
    diethyl carbonate 36.39
    propanediol butyl ether 22.68
    triethyl orthoformate 52.46
    p-tert-butyltoluene 33.84
    methyl 4-tert-butylbenzoate 60.38
    morpholine 123.82
    tert-butylamine 9.54
    n-dodecanol 14.7
    dimethoxymethane 92.86
    ethylene carbonate 67.43
    cyrene 76.11
    2-ethoxyethyl acetate 64.84
    2-ethylhexyl acetate 56.01
    1,2,4-trichlorobenzene 84.71
    4-methylpyridine 91.42
    dibutyl ether 40.75
    2,6-dimethyl-4-heptanol 24.17
    DEF 80.22
    dimethyl isosorbide 125.89
    tetrachloroethylene 85.41
    eugenol 50.86
    triacetin 53.58
    span 80 40.54
    1,4-butanediol 6.19
    1,1-dichloroethane 56.32
    2-methyl-1-pentanol 14.94
    methyl formate 33.71
    2-methyl-1-butanol 13.86
    n-decane 10.57
    butyronitrile 22.09
    3,7-dimethyl-1-octanol 22.08
    1-chlorooctane 29.47
    1-chlorotetradecane 13.84
    n-nonane 9.82
    undecane 7.71
    tert-butylcyclohexane 9.54
    cyclooctane 9.13
    cyclopentanol 44.35
    tetrahydropyran 118.85
    tert-amyl methyl ether 36.4
    2,5,8-trioxanonane 69.06
    1-hexene 16.18
    2-isopropoxyethanol 25.38
    2,2,2-trifluoroethanol 11.07
    methyl butyrate 51.54

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction