4-Phenyl-1H,3H-naphtho(1,8-cd)pyran-1,3-dione

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  • Identifiers

    CAS number
    56252-04-1

    Molecular formula
    C18H10O3

    SMILES
    C1=CC=C(C=C1)C2=C3C4=C(C=CC=C4C(=O)OC3=O)C=C2

    Safety labels

  • Odor profile

    Fragrance
    Sweet 56.57%
    Coumarinic 43.99%
    Balsamic 43.95%
    Floral 42.66%
    Phenolic 40.65%
    Powdery 38.71%
    Honey 34.49%
    Coconut 31.65%
    Bitter 30.35%
    Spicy 30.16%

     

    Flavor
    Bitter 90.57%
    Nitrile 19.4%
    Lovage 19.31%
    Very strong 19.28%
    Indole 19.04%
    Moth ball 18.73%
    Naphthelene 18.45%
    Cedarleaf 18.11%
    Animal 17.97%
    Tar 17.9%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.2

    pKa est.
    6.36 (neutral)

    Molecular weight
    274.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    549°C

    Melting point expt.

    • 241 - 243 °C

    Flash point

    • 245.04 ˚C est.

  • Synonyms

    • 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione
    • 56252-04-1
    • 6-phenyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione
    • 6-phenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
    • 4-Phenyl-1H,3H-naphtho(1,8-cd)pyran-1,3-dione
    • 6-phenyl-3-oxatricyclo(7.3.1.0^(5,13))trideca-1(13),5,7,9,11-pentaene-2,4-dione
    • 6-phenyl-3-oxatricyclo(7.3.1.05,13)trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
    • RefChem:100343
    • CHEMBL3593482
    • CHEBI:231995
    • DTXSID101255015
    • 56252-04-1

  • Applications

    4-Phenyl-1H,3H-naphtho(1,8-cd)pyran-1,3-dione (CAS 56252-04-1) may be used as an intermediate and core scaffold in the synthesis of polycyclic heterocycles for medicinal chemistry, and can serve as a precursor for dye and pigment development used in coatings and inks. It can also function as a starting point for functional polymers and participate in polymerization to support material development in plastics and coatings. In materials science, the naphtho-dione framework shows potential for organic electronic and photonic applications, including organic semiconductors or light-responsive materials, and is studied as a precursor for more complex polycyclic compounds in research and industry. Overall, its applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.25
    methanol 1.23
    isopropanol 0.53
    water 0.0
    ethyl acetate 3.65
    n-propanol 1.16
    acetone 5.73
    n-butanol 1.03
    acetonitrile 1.68
    DMF 74.42
    toluene 9.02
    isobutanol 0.76
    1,4-dioxane 12.77
    methyl acetate 5.97
    THF 30.24
    2-butanone 8.54
    n-pentanol 0.93
    sec-butanol 0.58
    n-hexane 0.02
    ethylene glycol 0.81
    NMP 82.87
    cyclohexane 0.04
    DMSO 22.98
    n-butyl acetate 7.41
    n-octanol 1.1
    chloroform 7.57
    n-propyl acetate 4.66
    acetic acid 3.39
    dichloromethane 12.58
    cyclohexanone 19.06
    propylene glycol 0.67
    isopropyl acetate 4.66
    DMAc 74.38
    2-ethoxyethanol 4.04
    isopentanol 1.45
    n-heptane 0.04
    ethyl formate 3.23
    1,2-dichloroethane 15.86
    n-hexanol 1.74
    2-methoxyethanol 10.45
    isobutyl acetate 4.43
    tetrachloromethane 0.34
    n-pentyl acetate 6.91
    transcutol 18.78
    n-heptanol 1.72
    ethylbenzene 3.25
    MIBK 6.71
    2-propoxyethanol 10.04
    tert-butanol 1.04
    MTBE 1.48
    2-butoxyethanol 7.25
    propionic acid 2.41
    o-xylene 4.38
    formic acid 1.66
    diethyl ether 1.4
    m-xylene 4.17
    p-xylene 3.72
    chlorobenzene 8.44
    dimethyl carbonate 11.09
    n-octane 0.04
    formamide 5.37
    cyclopentanone 34.99
    2-pentanone 6.46
    anisole 10.07
    cyclopentyl methyl ether 7.04
    gamma-butyrolactone 33.04
    1-methoxy-2-propanol 7.09
    pyridine 35.25
    3-pentanone 5.34
    furfural 38.84
    n-dodecane 0.1
    diethylene glycol 8.33
    diisopropyl ether 0.7
    tert-amyl alcohol 1.03
    acetylacetone 15.48
    n-hexadecane 0.13
    acetophenone 14.5
    methyl propionate 7.28
    isopentyl acetate 10.04
    trichloroethylene 45.74
    n-nonanol 1.45
    cyclohexanol 1.26
    benzyl alcohol 7.02
    2-ethylhexanol 2.19
    isooctanol 2.0
    dipropyl ether 2.35
    1,2-dichlorobenzene 9.76
    ethyl lactate 4.27
    propylene carbonate 12.4
    n-methylformamide 11.65
    2-pentanol 0.53
    n-pentane 0.02
    1-propoxy-2-propanol 6.68
    1-methoxy-2-propyl acetate 16.24
    2-(2-methoxypropoxy) propanol 10.54
    mesitylene 2.23
    ε-caprolactone 17.4
    p-cymene 3.25
    epichlorohydrin 56.06
    1,1,1-trichloroethane 4.46
    2-aminoethanol 1.51
    morpholine-4-carbaldehyde 51.69
    sulfolane 53.56
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 9.93
    n-hexyl acetate 7.23
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 10.74
    sec-butyl acetate 4.63
    tert-butyl acetate 8.49
    decalin 0.16
    glycerin 2.7
    diglyme 27.8
    acrylic acid 4.31
    isopropyl myristate 4.44
    n-butyric acid 3.53
    acetyl acetate 4.61
    di(2-ethylhexyl) phthalate 6.53
    ethyl propionate 4.9
    nitromethane 12.4
    1,2-diethoxyethane 7.5
    benzonitrile 11.78
    trioctyl phosphate 3.64
    1-bromopropane 2.53
    gamma-valerolactone 53.82
    n-decanol 1.18
    triethyl phosphate 5.89
    4-methyl-2-pentanol 0.91
    propionitrile 2.83
    vinylene carbonate 15.22
    1,1,2-trichlorotrifluoroethane 27.07
    DMS 15.09
    cumene 2.41
    2-octanol 1.05
    2-hexanone 5.99
    octyl acetate 4.81
    limonene 3.07
    1,2-dimethoxyethane 15.04
    ethyl orthosilicate 5.04
    tributyl phosphate 4.15
    diacetone alcohol 12.6
    N,N-dimethylaniline 7.49
    acrylonitrile 8.58
    aniline 8.86
    1,3-propanediol 2.45
    bromobenzene 9.46
    dibromomethane 4.67
    1,1,2,2-tetrachloroethane 24.19
    2-methyl-cyclohexyl acetate 8.73
    tetrabutyl urea 8.06
    diisobutyl methanol 1.97
    2-phenylethanol 9.79
    styrene 4.17
    dioctyl adipate 7.68
    dimethyl sulfate 26.29
    ethyl butyrate 5.68
    methyl lactate 6.81
    butyl lactate 6.16
    diethyl carbonate 5.02
    propanediol butyl ether 4.28
    triethyl orthoformate 5.73
    p-tert-butyltoluene 2.94
    methyl 4-tert-butylbenzoate 15.24
    morpholine 14.54
    tert-butylamine 0.5
    n-dodecanol 1.0
    dimethoxymethane 20.86
    ethylene carbonate 9.0
    cyrene 14.29
    2-ethoxyethyl acetate 13.2
    2-ethylhexyl acetate 8.1
    1,2,4-trichlorobenzene 15.66
    4-methylpyridine 26.25
    dibutyl ether 2.23
    2,6-dimethyl-4-heptanol 1.97
    DEF 15.35
    dimethyl isosorbide 30.53
    tetrachloroethylene 13.13
    eugenol 14.9
    triacetin 11.16
    span 80 7.68
    1,4-butanediol 0.76
    1,1-dichloroethane 3.65
    2-methyl-1-pentanol 1.63
    methyl formate 8.56
    2-methyl-1-butanol 1.18
    n-decane 0.12
    butyronitrile 2.47
    3,7-dimethyl-1-octanol 2.0
    1-chlorooctane 1.0
    1-chlorotetradecane 0.65
    n-nonane 0.07
    undecane 0.11
    tert-butylcyclohexane 0.16
    cyclooctane 0.02
    cyclopentanol 2.04
    tetrahydropyran 5.74
    tert-amyl methyl ether 1.89
    2,5,8-trioxanonane 21.62
    1-hexene 0.24
    2-isopropoxyethanol 3.23
    2,2,2-trifluoroethanol 1.63
    methyl butyrate 6.43

    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