6-Methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one

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  • Identifiers

    CAS number
    477-89-4

    Molecular formula
    C12H11NO4

    SMILES
    CN1C(=O)C=C(C2=C1C3=C(C=C2)OCO3)OC

    Safety labels

  • Odor profile

    Fragrance
    Sweet 39.06%
    Phenolic 36.21%
    Spicy 31.15%
    Vanilla 31.14%
    Powdery 30.91%
    Floral 28.25%
    Odorless 26.68%
    Fruity 24.47%
    Animal 23.12%
    Creamy 22.75%

     

    Flavor
    Bitter 93.81%
    Bland 20.9%
    Parsley 20.08%
    Sweet-like 19.44%
    Cedarleaf 19.4%
    Lovage 18.96%
    Eugenol 18.77%
    Odorless 18.52%
    Ripe apricot 18.2%
    Very strong 18.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    5.75 (weak acid)

    Molecular weight
    233.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    421°C

    Melting point expt.

    • 202 - 203 °C

    Flash point

    • 195.98 ˚C est.

  • Synonyms

    • 6-Methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one
    • 6-Methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
    • RefChem:123910
    • Casimiroin
    • 477-89-4
    • 6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one
    • 1X2A1U6BH3
    • 6-methoxy-9-methyl[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
    • 1,3-Dioxolo(4,5-h)quinolin-8(9H)-one, 6-methoxy-9-methyl-
    • 6-Methoxy-9-methyl-1,3-Dioxolo(4,5-h)quinolin-8(9H)-one
    • XM5
    • UNII-1X2A1U6BH3
    • CASIMIROINE
    • CASIMIROIN [MI]
    • CHEBI:3452
    • CHEMBL492762
    • orb1740272
    • SCHEMBL6244731
    • SCHEMBL30362945
    • BDBM29210
    • DTXSID90197256
    • 6-METHOXY-9-METHYL-2H,8H,9H-[1,3]DIOXOLO[4,5-H]QUINOLIN-8-ONE
    • DB08744
    • NS00068422
    • Q27097930
    • 4-Methoxy-1-methyl-7,8-methylenedioxy-2(1H)-quinolinone
    • 6-methoxy-9-methyl[1,3]dioxolo[4,5-h]quinolin-8(9 h)-one
    • 6-Methoxy-9-methyl-1,3-dioxolo[4,5-h]quinolin-8(9H)-one, 9CI
    • 6-Methoxy-9-methyl-2H-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
    • 6-Methoxy-9-methyl-9-hydro-2H-1,3-dioxolano[4,5-h]quinolin-8-one
    • 477-89-4

  • Applications

    6-Methoxy-9-methyl-(1,3)dioxolo(4,5-h)quinolin-8(9H)-one (CAS 477-89-4) is used as an intermediate in pharmaceutical synthesis, serving as a heterocyclic scaffold for the development of related drug candidates. It is also commonly employed as a building block in organic synthesis to access more complex quinolinone derivatives. In materials science, the conjugated dioxolo-quinolinone framework of the compound has been explored for potential optoelectronic applications and as a fluorescent probe in research settings. Additionally, it can function as a dye precursor for coatings and inks, enabling colorant development in industrial formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.69
    methanol 6.1
    isopropanol 2.87
    water 1.38
    ethyl acetate 20.79
    n-propanol 2.65
    acetone 23.37
    n-butanol 2.81
    acetonitrile 23.9
    DMF 50.83
    toluene 5.73
    isobutanol 2.85
    1,4-dioxane 32.33
    methyl acetate 25.54
    THF 31.3
    2-butanone 15.15
    n-pentanol 3.37
    sec-butanol 2.19
    n-hexane 0.16
    ethylene glycol 8.62
    NMP 69.55
    cyclohexane 0.69
    DMSO 72.44
    n-butyl acetate 15.69
    n-octanol 4.48
    chloroform 37.77
    n-propyl acetate 17.01
    acetic acid 32.24
    dichloromethane 59.97
    cyclohexanone 36.96
    propylene glycol 1.66
    isopropyl acetate 13.88
    DMAc 71.77
    2-ethoxyethanol 18.23
    isopentanol 4.32
    n-heptane 0.49
    ethyl formate 25.4
    1,2-dichloroethane 37.3
    n-hexanol 5.33
    2-methoxyethanol 27.89
    isobutyl acetate 12.33
    tetrachloromethane 7.72
    n-pentyl acetate 11.87
    transcutol 23.51
    n-heptanol 5.04
    ethylbenzene 5.01
    MIBK 10.89
    2-propoxyethanol 24.23
    tert-butanol 5.84
    MTBE 3.37
    2-butoxyethanol 17.69
    propionic acid 11.08
    o-xylene 7.33
    formic acid 36.36
    diethyl ether 4.18
    m-xylene 6.07
    p-xylene 9.43
    chlorobenzene 17.67
    dimethyl carbonate 26.13
    n-octane 0.35
    formamide 55.93
    cyclopentanone 37.78
    2-pentanone 11.95
    anisole 13.93
    cyclopentyl methyl ether 11.9
    gamma-butyrolactone 68.2
    1-methoxy-2-propanol 12.78
    pyridine 35.19
    3-pentanone 11.98
    furfural 86.93
    n-dodecane 0.52
    diethylene glycol 36.87
    diisopropyl ether 2.15
    tert-amyl alcohol 4.03
    acetylacetone 31.64
    n-hexadecane 0.62
    acetophenone 25.74
    methyl propionate 19.73
    isopentyl acetate 15.85
    trichloroethylene 72.97
    n-nonanol 4.93
    cyclohexanol 6.41
    benzyl alcohol 16.09
    2-ethylhexanol 5.97
    isooctanol 5.13
    dipropyl ether 5.14
    1,2-dichlorobenzene 23.69
    ethyl lactate 13.51
    propylene carbonate 43.34
    n-methylformamide 28.91
    2-pentanol 1.96
    n-pentane 0.16
    1-propoxy-2-propanol 12.61
    1-methoxy-2-propyl acetate 21.61
    2-(2-methoxypropoxy) propanol 17.91
    mesitylene 4.36
    ε-caprolactone 34.81
    p-cymene 6.47
    epichlorohydrin 61.68
    1,1,1-trichloroethane 25.08
    2-aminoethanol 5.63
    morpholine-4-carbaldehyde 68.5
    sulfolane 74.33
    2,2,4-trimethylpentane 0.25
    2-methyltetrahydrofuran 17.88
    n-hexyl acetate 12.34
    isooctane 0.19
    2-(2-butoxyethoxy)ethanol 17.66
    sec-butyl acetate 10.92
    tert-butyl acetate 13.33
    decalin 0.77
    glycerin 11.15
    diglyme 41.49
    acrylic acid 19.31
    isopropyl myristate 6.7
    n-butyric acid 14.95
    acetyl acetate 25.87
    di(2-ethylhexyl) phthalate 11.22
    ethyl propionate 16.06
    nitromethane 84.24
    1,2-diethoxyethane 10.75
    benzonitrile 29.3
    trioctyl phosphate 7.99
    1-bromopropane 7.21
    gamma-valerolactone 63.85
    n-decanol 4.03
    triethyl phosphate 15.95
    4-methyl-2-pentanol 2.63
    propionitrile 14.42
    vinylene carbonate 51.65
    1,1,2-trichlorotrifluoroethane 59.38
    DMS 23.15
    cumene 4.9
    2-octanol 3.18
    2-hexanone 12.64
    octyl acetate 8.49
    limonene 6.6
    1,2-dimethoxyethane 37.1
    ethyl orthosilicate 13.09
    tributyl phosphate 9.37
    diacetone alcohol 17.03
    N,N-dimethylaniline 12.23
    acrylonitrile 28.59
    aniline 11.68
    1,3-propanediol 9.43
    bromobenzene 17.45
    dibromomethane 26.5
    1,1,2,2-tetrachloroethane 44.01
    2-methyl-cyclohexyl acetate 17.16
    tetrabutyl urea 12.96
    diisobutyl methanol 4.25
    2-phenylethanol 18.25
    styrene 5.41
    dioctyl adipate 11.84
    dimethyl sulfate 49.29
    ethyl butyrate 16.59
    methyl lactate 16.8
    butyl lactate 10.49
    diethyl carbonate 18.03
    propanediol butyl ether 9.16
    triethyl orthoformate 13.57
    p-tert-butyltoluene 5.2
    methyl 4-tert-butylbenzoate 21.78
    morpholine 24.29
    tert-butylamine 2.59
    n-dodecanol 3.37
    dimethoxymethane 32.47
    ethylene carbonate 40.82
    cyrene 30.93
    2-ethoxyethyl acetate 19.47
    2-ethylhexyl acetate 13.26
    1,2,4-trichlorobenzene 28.64
    4-methylpyridine 27.99
    dibutyl ether 4.47
    2,6-dimethyl-4-heptanol 4.25
    DEF 24.87
    dimethyl isosorbide 36.77
    tetrachloroethylene 37.98
    eugenol 23.19
    triacetin 19.35
    span 80 11.71
    1,4-butanediol 5.25
    1,1-dichloroethane 17.81
    2-methyl-1-pentanol 4.83
    methyl formate 41.62
    2-methyl-1-butanol 3.43
    n-decane 0.68
    butyronitrile 11.82
    3,7-dimethyl-1-octanol 5.15
    1-chlorooctane 3.25
    1-chlorotetradecane 1.89
    n-nonane 0.51
    undecane 0.58
    tert-butylcyclohexane 0.59
    cyclooctane 0.33
    cyclopentanol 7.75
    tetrahydropyran 11.71
    tert-amyl methyl ether 3.69
    2,5,8-trioxanonane 31.33
    1-hexene 0.87
    2-isopropoxyethanol 14.08
    2,2,2-trifluoroethanol 40.27
    methyl butyrate 21.03

    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