4,7-Methanoisobenzofuran-1,3-dione, 5,6-dibromohexahydro-

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  • Identifiers

    CAS number
    5455-81-2

    Molecular formula
    C9H8Br2O3

    SMILES
    C1C2C3C(C1C(C2Br)Br)C(=O)OC3=O

  • Odor profile

    Fragrance
    Odorless 72.04%
    Nutty 24.28%
    Spicy 20.75%
    Woody 17.66%
    Burnt 17.39%
    Savory 14.21%
    Cooling 14.2%
    Popcorn 13.48%
    Bitter 13.45%
    Roasted 13.18%

     

    Flavor
    Bitter 87.62%
    Odorless 25.61%
    Sweet-like 21.12%
    Cedarleaf 20.48%
    Bland 20.42%
    Nitrile 19.42%
    Alkaline 18.58%
    Lovage 18.35%
    Basil 18.22%
    Oriental 18.19%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    5.11 (weak acid)

    Molecular weight
    323.97 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    494°C

    Flash point

    • 164.26 ˚C est.

  • Synonyms

    • 5455-81-2
    • 5,6-Dibromohexahydro-4,7-methanoisobenzofuran-1,3-dione
    • 5,6-dibromohexahydro-4,7-methano-2-benzofuran-1,3-dione
    • NSC 6139
    • 4,7-Methanoisobenzofuran-1,3-dione, 5,6-dibromohexahydro-
    • MFCD00464407
    • 5,6-Dibromo-2,3-norbornanedicarboxylic anhydride
    • NSC 122103
    • 8,9-dibromo-4-oxatricyclo[5.2.1.02,6]decane-3,5-dione
    • DTXSID40884164
    • 2,3-Norbornanedicarboxylic anhydride, 5,6-dibromo-
    • 2, 5,6-dibromo-
    • 4,3-dione, 5,6-dibromohexahydro-
    • 5,3-norbornanedicarboxylic anhydride
    • 5,7-methanoisobenzofuran-1,3-dione
    • 8,9-DIBROMO-4-OXATRICYCLO[5.2.1.0(2),?]DECANE-3,5-DIONE
    • 63179-93-1
    • SCHEMBL4757874
    • NSC6139
    • HHFFMUZIOYHTFC-UHFFFAOYSA-N
    • DTXCID701023628
    • ALBB-010652
    • NSC-6139
    • NSC122103
    • NSC140602
    • STK366650
    • AKOS005172593
    • NSC-122103
    • NSC-140602
    • LS-03638
    • CS-0331813
    • H25787

  • Applications

    The chemical 4,7-Methanoisobenzofuran-1,3-dione, 5,6-dibromohexahydro- (CAS 5455-81-2) is primarily used as an intermediate and building block in organic synthesis, providing a rigid norbornane-fused isobenzofuranone scaffold that can be converted into more complex heterocycles and conjugated systems. It is commonly evaluated in pharmaceutical and agrochemical research as a precursor for developing new compounds. In polymer and materials chemistry, it can serve as a functionalized core or a crosslinking precursor for specialty polymers and coatings, enabling improved thermal stability and mechanical properties. It may also be used in specialty coatings and inks as a reactive monomer or co-monomer, contributing to adhesion and durability. Its use is typically as an intermediate and fairly specialized; applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 32.2
    methanol 51.93
    isopropanol 31.0
    water 3.32
    ethyl acetate 84.18
    n-propanol 31.92
    acetone 167.63
    n-butanol 33.4
    acetonitrile 78.52
    DMF 455.56
    toluene 35.72
    isobutanol 29.26
    1,4-dioxane 139.7
    methyl acetate 98.83
    THF 224.87
    2-butanone 110.73
    n-pentanol 34.25
    sec-butanol 31.41
    n-hexane 2.47
    ethylene glycol 39.56
    NMP 397.05
    cyclohexane 4.31
    DMSO 376.16
    n-butyl acetate 70.03
    n-octanol 35.84
    chloroform 154.24
    n-propyl acetate 67.74
    acetic acid 72.83
    dichloromethane 143.78
    cyclohexanone 150.55
    propylene glycol 32.81
    isopropyl acetate 71.75
    DMAc 329.58
    2-ethoxyethanol 102.17
    isopentanol 35.51
    n-heptane 4.89
    ethyl formate 75.39
    1,2-dichloroethane 111.6
    n-hexanol 41.86
    2-methoxyethanol 166.73
    isobutyl acetate 45.82
    tetrachloromethane 30.06
    n-pentyl acetate 61.92
    transcutol 255.25
    n-heptanol 32.1
    ethylbenzene 25.6
    MIBK 83.32
    2-propoxyethanol 125.68
    tert-butanol 48.35
    MTBE 40.73
    2-butoxyethanol 78.5
    propionic acid 53.76
    o-xylene 35.3
    formic acid 69.48
    diethyl ether 49.15
    m-xylene 38.64
    p-xylene 36.09
    chlorobenzene 61.13
    dimethyl carbonate 110.16
    n-octane 3.27
    formamide 138.98
    cyclopentanone 225.25
    2-pentanone 109.6
    anisole 71.12
    cyclopentyl methyl ether 91.6
    gamma-butyrolactone 247.28
    1-methoxy-2-propanol 146.28
    pyridine 120.47
    3-pentanone 92.55
    furfural 272.7
    n-dodecane 3.98
    diethylene glycol 153.18
    diisopropyl ether 23.39
    tert-amyl alcohol 41.22
    acetylacetone 218.91
    n-hexadecane 4.7
    acetophenone 105.26
    methyl propionate 103.34
    isopentyl acetate 62.78
    trichloroethylene 232.38
    n-nonanol 35.46
    cyclohexanol 42.65
    benzyl alcohol 68.66
    2-ethylhexanol 34.81
    isooctanol 28.55
    dipropyl ether 40.88
    1,2-dichlorobenzene 76.67
    ethyl lactate 67.6
    propylene carbonate 136.54
    n-methylformamide 170.64
    2-pentanol 32.25
    n-pentane 3.14
    1-propoxy-2-propanol 92.95
    1-methoxy-2-propyl acetate 112.28
    2-(2-methoxypropoxy) propanol 100.98
    mesitylene 29.74
    ε-caprolactone 125.86
    p-cymene 29.41
    epichlorohydrin 238.72
    1,1,1-trichloroethane 94.84
    2-aminoethanol 47.16
    morpholine-4-carbaldehyde 337.36
    sulfolane 376.5
    2,2,4-trimethylpentane 3.03
    2-methyltetrahydrofuran 107.51
    n-hexyl acetate 75.5
    isooctane 2.89
    2-(2-butoxyethoxy)ethanol 115.6
    sec-butyl acetate 51.3
    tert-butyl acetate 83.78
    decalin 4.48
    glycerin 82.65
    diglyme 204.28
    acrylic acid 75.36
    isopropyl myristate 42.59
    n-butyric acid 64.4
    acetyl acetate 90.26
    di(2-ethylhexyl) phthalate 52.89
    ethyl propionate 72.36
    nitromethane 252.86
    1,2-diethoxyethane 80.52
    benzonitrile 88.34
    trioctyl phosphate 40.85
    1-bromopropane 39.48
    gamma-valerolactone 295.38
    n-decanol 29.26
    triethyl phosphate 46.33
    4-methyl-2-pentanol 28.16
    propionitrile 57.11
    vinylene carbonate 140.48
    1,1,2-trichlorotrifluoroethane 257.29
    DMS 99.96
    cumene 22.37
    2-octanol 27.83
    2-hexanone 77.46
    octyl acetate 51.08
    limonene 35.77
    1,2-dimethoxyethane 176.01
    ethyl orthosilicate 40.7
    tributyl phosphate 47.08
    diacetone alcohol 119.4
    N,N-dimethylaniline 68.67
    acrylonitrile 97.29
    aniline 58.56
    1,3-propanediol 61.89
    bromobenzene 59.08
    dibromomethane 79.27
    1,1,2,2-tetrachloroethane 182.53
    2-methyl-cyclohexyl acetate 63.15
    tetrabutyl urea 74.27
    diisobutyl methanol 28.56
    2-phenylethanol 76.9
    styrene 29.09
    dioctyl adipate 59.71
    dimethyl sulfate 212.31
    ethyl butyrate 61.29
    methyl lactate 113.34
    butyl lactate 66.79
    diethyl carbonate 47.49
    propanediol butyl ether 87.73
    triethyl orthoformate 48.22
    p-tert-butyltoluene 29.1
    methyl 4-tert-butylbenzoate 102.73
    morpholine 132.63
    tert-butylamine 26.47
    n-dodecanol 24.36
    dimethoxymethane 239.77
    ethylene carbonate 104.61
    cyrene 144.81
    2-ethoxyethyl acetate 91.18
    2-ethylhexyl acetate 53.65
    1,2,4-trichlorobenzene 97.84
    4-methylpyridine 109.1
    dibutyl ether 35.43
    2,6-dimethyl-4-heptanol 28.56
    DEF 156.82
    dimethyl isosorbide 194.45
    tetrachloroethylene 124.14
    eugenol 117.94
    triacetin 99.23
    span 80 86.71
    1,4-butanediol 38.4
    1,1-dichloroethane 78.06
    2-methyl-1-pentanol 34.33
    methyl formate 165.43
    2-methyl-1-butanol 31.97
    n-decane 5.4
    butyronitrile 53.32
    3,7-dimethyl-1-octanol 37.89
    1-chlorooctane 23.78
    1-chlorotetradecane 13.39
    n-nonane 4.49
    undecane 4.6
    tert-butylcyclohexane 3.95
    cyclooctane 2.8
    cyclopentanol 59.55
    tetrahydropyran 70.47
    tert-amyl methyl ether 43.11
    2,5,8-trioxanonane 157.28
    1-hexene 10.99
    2-isopropoxyethanol 76.18
    2,2,2-trifluoroethanol 88.12
    methyl butyrate 88.53

    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