Isophthalide

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  • Identifiers

    CAS number
    553-86-6

    Molecular formula
    C8H6O2

    SMILES
    C1C2=CC=CC=C2OC1=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Coumarinic 73.49%
    Sweet 68.96%
    Coconut 63.4%
    Spicy 58.83%
    Nutty 53.09%
    Hay 48.69%
    Phenolic 47.14%
    Herbal 46.54%
    Vanilla 44.71%
    Cinnamon 43.8%

     

    Flavor
    Sweet 84.31%
    Tonka 58.25%
    Herbal 54.62%
    Coconut 53.3%
    Tobacco 48.2%
    Almond 44.07%
    Creamy 41.58%
    Coumarin 41.45%
    Bitter 38.35%
    Balsam 37.26%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    8.28 (weak base)

    Molecular weight
    134.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    255°C

    Flash point

    • 132.71 ˚C est.

  • Synonyms

    • 2-Coumaranone
    • 553-86-6
    • Benzofuran-2(3H)-one
    • 2(3H)-Benzofuranone
    • 3H-benzofuran-2-one
    • Benzofuranone
    • Isophthalide
    • Benzofuran-2-one
    • (3H)-Benzofuran-2-one
    • 3H-1-benzofuran-2-one
    • Isocoumaranone
    • 2-Benzofuranone
    • 2-Coumarotioiie
    • 2,3-dihydrobenzofuran-2-one
    • CUMARANONE
    • 2-COUMARONE
    • 4K47Z4Q1E7
    • EINECS 209-052-0
    • MFCD00005856
    • NSC-227414
    • AI3-36067
    • CHEMBL284584
    • DTXSID70203829
    • EC 209-052-0
    • BENZO(B)FURAN-2(3H)-ONE
    • NSC 227414
    • 1-Benzofuran-2(3H)-one
    • benzo[b]furan-2(3H)-one
    • BENZENEACETIC ACID, 2-HYDROXY-, .GAMMA.-LACTONE
    • ACETIC ACID, (O-HYDROXYPHENYL)-, .GAMMA.-LACTONE
    • UNII-4K47Z4Q1E7
    • 2,3-dihydro-1-benzofuran-2-one
    • NSC227414
    • 2-Coumaranone, 97%
    • SCHEMBL44758
    • 2,3-dihydro-2-benzofuranone
    • 1-Benzofuran-2(3H)-one #
    • DTXCID50126320
    • CS-M0764
    • BDBM50029069
    • AKOS009031219
    • 2-coumaranone; (3h)-benzofuran-2-one
    • AS-18012
    • SY038967
    • DB-022573
    • C1445
    • NS00007800
    • EN300-21214
    • A26517
    • L10016
    • BENZENEACETIC ACID, 2-HYDROXY-, GAMMA-LACTONE
    • Q27259814
    • ACETIC ACID, (O-HYDROXYPHENYL)-, GAMMA-LACTONE
    • 2-Coumaranone;2,3-Dihydrobenzofuran-2-one;2(3H)-benzofuranone
    • 209-052-0

  • Applications

    Isophthalide, CAS 553-86-6, is primarily used as an intermediate in organic synthesis, serving as a precursor for pharmaceutical compounds and a range of industrial products; it provides a building block for high-performance polymers such as polyimides; it also serves as a precursor in the production of dyes and pigments for textiles and printing; related isoindolinone derivatives derived from isophthalide are evaluated for fragrance applications in perfumery; and it may be used as a chemical intermediate in coatings, resins, and ink formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 77.29
    methanol 87.18
    isopropanol 50.36
    water 2.59
    ethyl acetate 192.34
    n-propanol 74.86
    acetone 199.57
    n-butanol 32.93
    acetonitrile 264.69
    DMF 609.87
    toluene 30.51
    isobutanol 39.69
    1,4-dioxane 603.77
    methyl acetate 250.14
    THF 140.47
    2-butanone 141.44
    n-pentanol 44.58
    sec-butanol 49.31
    n-hexane 1.67
    ethylene glycol 119.23
    NMP 257.09
    cyclohexane 1.49
    DMSO 440.93
    n-butyl acetate 51.68
    n-octanol 49.05
    chloroform 171.1
    n-propyl acetate 67.2
    acetic acid 109.56
    dichloromethane 171.92
    cyclohexanone 97.35
    propylene glycol 75.06
    isopropyl acetate 64.52
    DMAc 381.66
    2-ethoxyethanol 193.08
    isopentanol 35.96
    n-heptane 2.62
    ethyl formate 85.39
    1,2-dichloroethane 109.32
    n-hexanol 47.27
    2-methoxyethanol 299.12
    isobutyl acetate 40.44
    tetrachloromethane 13.31
    n-pentyl acetate 42.67
    transcutol 1047.73
    n-heptanol 30.47
    ethylbenzene 21.34
    MIBK 53.38
    2-propoxyethanol 163.26
    tert-butanol 67.16
    MTBE 48.01
    2-butoxyethanol 94.61
    propionic acid 119.9
    o-xylene 23.92
    formic acid 96.83
    diethyl ether 80.62
    m-xylene 25.19
    p-xylene 28.59
    chlorobenzene 55.43
    dimethyl carbonate 130.98
    n-octane 1.99
    formamide 211.97
    cyclopentanone 137.23
    2-pentanone 82.7
    anisole 116.68
    cyclopentyl methyl ether 59.45
    gamma-butyrolactone 207.67
    1-methoxy-2-propanol 192.05
    pyridine 198.6
    3-pentanone 80.03
    furfural 217.1
    n-dodecane 3.83
    diethylene glycol 241.09
    diisopropyl ether 19.64
    tert-amyl alcohol 53.0
    acetylacetone 168.16
    n-hexadecane 4.35
    acetophenone 89.22
    methyl propionate 180.22
    isopentyl acetate 46.19
    trichloroethylene 201.92
    n-nonanol 44.68
    cyclohexanol 31.14
    benzyl alcohol 76.21
    2-ethylhexanol 28.44
    isooctanol 26.72
    dipropyl ether 36.54
    1,2-dichlorobenzene 55.36
    ethyl lactate 62.67
    propylene carbonate 90.89
    n-methylformamide 262.55
    2-pentanol 27.17
    n-pentane 1.12
    1-propoxy-2-propanol 95.18
    1-methoxy-2-propyl acetate 105.31
    2-(2-methoxypropoxy) propanol 152.42
    mesitylene 16.78
    ε-caprolactone 104.51
    p-cymene 15.92
    epichlorohydrin 228.91
    1,1,1-trichloroethane 69.15
    2-aminoethanol 116.85
    morpholine-4-carbaldehyde 440.7
    sulfolane 194.67
    2,2,4-trimethylpentane 1.63
    2-methyltetrahydrofuran 91.88
    n-hexyl acetate 81.66
    isooctane 1.74
    2-(2-butoxyethoxy)ethanol 236.43
    sec-butyl acetate 44.83
    tert-butyl acetate 65.95
    decalin 3.53
    glycerin 151.23
    diglyme 401.8
    acrylic acid 129.79
    isopropyl myristate 40.31
    n-butyric acid 61.58
    acetyl acetate 98.95
    di(2-ethylhexyl) phthalate 40.44
    ethyl propionate 77.89
    nitromethane 496.89
    1,2-diethoxyethane 157.54
    benzonitrile 82.45
    trioctyl phosphate 28.99
    1-bromopropane 35.03
    gamma-valerolactone 276.85
    n-decanol 36.12
    triethyl phosphate 34.04
    4-methyl-2-pentanol 24.37
    propionitrile 117.66
    vinylene carbonate 110.36
    1,1,2-trichlorotrifluoroethane 181.79
    DMS 129.08
    cumene 17.66
    2-octanol 24.76
    2-hexanone 60.38
    octyl acetate 49.79
    limonene 18.14
    1,2-dimethoxyethane 293.29
    ethyl orthosilicate 30.11
    tributyl phosphate 38.21
    diacetone alcohol 98.07
    N,N-dimethylaniline 68.09
    acrylonitrile 206.45
    aniline 62.66
    1,3-propanediol 100.19
    bromobenzene 51.86
    dibromomethane 81.19
    1,1,2,2-tetrachloroethane 144.83
    2-methyl-cyclohexyl acetate 40.03
    tetrabutyl urea 55.43
    diisobutyl methanol 21.68
    2-phenylethanol 65.34
    styrene 28.62
    dioctyl adipate 56.59
    dimethyl sulfate 189.27
    ethyl butyrate 47.51
    methyl lactate 114.31
    butyl lactate 51.96
    diethyl carbonate 42.12
    propanediol butyl ether 126.91
    triethyl orthoformate 40.03
    p-tert-butyltoluene 16.51
    methyl 4-tert-butylbenzoate 81.2
    morpholine 393.26
    tert-butylamine 31.68
    n-dodecanol 29.71
    dimethoxymethane 303.72
    ethylene carbonate 85.63
    cyrene 103.68
    2-ethoxyethyl acetate 106.88
    2-ethylhexyl acetate 34.01
    1,2,4-trichlorobenzene 73.23
    4-methylpyridine 124.79
    dibutyl ether 51.88
    2,6-dimethyl-4-heptanol 21.68
    DEF 144.34
    dimethyl isosorbide 179.5
    tetrachloroethylene 79.4
    eugenol 102.24
    triacetin 119.03
    span 80 94.96
    1,4-butanediol 63.28
    1,1-dichloroethane 83.32
    2-methyl-1-pentanol 39.27
    methyl formate 210.69
    2-methyl-1-butanol 32.24
    n-decane 4.72
    butyronitrile 54.93
    3,7-dimethyl-1-octanol 48.41
    1-chlorooctane 23.57
    1-chlorotetradecane 13.35
    n-nonane 3.87
    undecane 4.22
    tert-butylcyclohexane 3.67
    cyclooctane 0.91
    cyclopentanol 42.92
    tetrahydropyran 114.39
    tert-amyl methyl ether 38.93
    2,5,8-trioxanonane 313.44
    1-hexene 9.74
    2-isopropoxyethanol 120.24
    2,2,2-trifluoroethanol 74.89
    methyl butyrate 77.76

    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