2-Oxo-2H-1-benzopyran-4-carboxylic acid

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  • Identifiers

    CAS number
    27393-46-0

    Molecular formula
    C10H6O4

    SMILES
    C1=CC=C2C(=C1)C(=CC(=O)O2)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 52.91%
    Balsamic 37.24%
    Phenolic 37.12%
    Burnt 34.19%
    Nutty 33.03%
    Sour 28.41%
    Sweet 28.31%
    Honey 26.5%
    Bitter 25.22%
    Powdery 25.11%

     

    Flavor
    Odorless 39.34%
    Bitter 38.87%
    Balsam 35.5%
    Nutty 33.77%
    Mild 31.55%
    Faint 30.04%
    Phenolic 28.07%
    Balsamic 27.68%
    Sour 27.49%
    Sweet 26.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    4.65 (weak acid)

    Molecular weight
    190.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    380°C

    Flash point

    • 184.65 ˚C est.

  • Synonyms

    • 27393-46-0
    • 2-oxo-2h-1-benzopyran-4-carboxylic acid
    • RefChem:1064041
    • 2-Oxo-2H-chromene-4-carboxylic acid
    • COUMARIN-4-CARBOXYLIC ACID
    • 2-oxochromene-4-carboxylic acid
    • SCHEMBL2808427
    • SCHEMBL8636466
    • DTXSID60345540
    • CHEBI:173902
    • DORZTUIRBJRLFD-UHFFFAOYSA-N
    • 2-Oxo-2H-chromene-4-carboxylicacid
    • DB-393469
    • 27393-46-0

  • Applications

    2-Oxo-2H-1-benzopyran-4-carboxylic acid (CAS 27393-46-0) is primarily used as a synthetic building block, providing a coumarin/isocoumarin-like scaffold for the preparation of complex heterocyclic compounds. Applications include pharmaceutical intermediates; agrochemical intermediates; building blocks for polymers and plastics via derivatization to acid chlorides or esters; fragrance research as a precursor for aroma compounds; coatings and inks as a functional intermediate or additive.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 31.93
    methanol 57.19
    isopropanol 21.37
    water 1.48
    ethyl acetate 16.45
    n-propanol 22.62
    acetone 75.22
    n-butanol 17.58
    acetonitrile 36.49
    DMF 417.09
    toluene 10.5
    isobutanol 14.19
    1,4-dioxane 53.77
    methyl acetate 34.57
    THF 82.36
    2-butanone 53.8
    n-pentanol 15.86
    sec-butanol 16.15
    n-hexane 0.3
    ethylene glycol 26.05
    NMP 128.83
    cyclohexane 0.41
    DMSO 361.85
    n-butyl acetate 13.45
    n-octanol 16.74
    chloroform 4.63
    n-propyl acetate 11.14
    acetic acid 14.25
    dichloromethane 20.02
    cyclohexanone 36.05
    propylene glycol 7.95
    isopropyl acetate 10.6
    DMAc 265.04
    2-ethoxyethanol 47.6
    isopentanol 17.15
    n-heptane 1.06
    ethyl formate 17.83
    1,2-dichloroethane 33.08
    n-hexanol 15.31
    2-methoxyethanol 96.27
    isobutyl acetate 4.64
    tetrachloromethane 1.24
    n-pentyl acetate 16.56
    transcutol 50.32
    n-heptanol 16.82
    ethylbenzene 7.19
    MIBK 16.29
    2-propoxyethanol 42.55
    tert-butanol 29.58
    MTBE 15.47
    2-butoxyethanol 33.23
    propionic acid 10.35
    o-xylene 11.28
    formic acid 19.78
    diethyl ether 17.48
    m-xylene 8.76
    p-xylene 8.48
    chlorobenzene 8.09
    dimethyl carbonate 23.51
    n-octane 0.97
    formamide 73.77
    cyclopentanone 69.72
    2-pentanone 29.97
    anisole 19.49
    cyclopentyl methyl ether 20.64
    gamma-butyrolactone 54.53
    1-methoxy-2-propanol 44.3
    pyridine 44.55
    3-pentanone 26.24
    furfural 51.19
    n-dodecane 1.55
    diethylene glycol 43.41
    diisopropyl ether 4.1
    tert-amyl alcohol 20.39
    acetylacetone 32.37
    n-hexadecane 1.76
    acetophenone 23.9
    methyl propionate 27.1
    isopentyl acetate 11.9
    trichloroethylene 27.74
    n-nonanol 16.73
    cyclohexanol 11.54
    benzyl alcohol 20.54
    2-ethylhexanol 9.79
    isooctanol 12.33
    dipropyl ether 13.22
    1,2-dichlorobenzene 10.19
    ethyl lactate 9.11
    propylene carbonate 13.43
    n-methylformamide 109.93
    2-pentanol 9.83
    n-pentane 0.44
    1-propoxy-2-propanol 23.38
    1-methoxy-2-propyl acetate 20.23
    2-(2-methoxypropoxy) propanol 30.49
    mesitylene 5.39
    ε-caprolactone 24.59
    p-cymene 8.51
    epichlorohydrin 84.7
    1,1,1-trichloroethane 6.95
    2-aminoethanol 25.67
    morpholine-4-carbaldehyde 115.16
    sulfolane 89.66
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 35.46
    n-hexyl acetate 19.12
    isooctane 0.34
    2-(2-butoxyethoxy)ethanol 36.78
    sec-butyl acetate 6.36
    tert-butyl acetate 12.34
    decalin 0.77
    glycerin 18.45
    diglyme 72.3
    acrylic acid 11.61
    isopropyl myristate 10.84
    n-butyric acid 10.74
    acetyl acetate 8.36
    di(2-ethylhexyl) phthalate 11.17
    ethyl propionate 11.95
    nitromethane 60.34
    1,2-diethoxyethane 25.4
    benzonitrile 21.11
    trioctyl phosphate 10.16
    1-bromopropane 10.1
    gamma-valerolactone 74.97
    n-decanol 14.17
    triethyl phosphate 9.31
    4-methyl-2-pentanol 6.58
    propionitrile 27.09
    vinylene carbonate 14.67
    1,1,2-trichlorotrifluoroethane 31.8
    DMS 16.32
    cumene 5.78
    2-octanol 12.16
    2-hexanone 19.54
    octyl acetate 15.26
    limonene 9.18
    1,2-dimethoxyethane 90.38
    ethyl orthosilicate 8.79
    tributyl phosphate 9.38
    diacetone alcohol 27.55
    N,N-dimethylaniline 21.2
    acrylonitrile 45.48
    aniline 15.63
    1,3-propanediol 33.38
    bromobenzene 6.83
    dibromomethane 8.51
    1,1,2,2-tetrachloroethane 20.85
    2-methyl-cyclohexyl acetate 10.73
    tetrabutyl urea 20.66
    diisobutyl methanol 7.05
    2-phenylethanol 19.61
    styrene 6.99
    dioctyl adipate 14.26
    dimethyl sulfate 45.81
    ethyl butyrate 10.66
    methyl lactate 17.93
    butyl lactate 11.84
    diethyl carbonate 7.81
    propanediol butyl ether 19.6
    triethyl orthoformate 9.35
    p-tert-butyltoluene 7.39
    methyl 4-tert-butylbenzoate 27.48
    morpholine 59.04
    tert-butylamine 11.79
    n-dodecanol 11.72
    dimethoxymethane 116.72
    ethylene carbonate 11.93
    cyrene 28.87
    2-ethoxyethyl acetate 23.12
    2-ethylhexyl acetate 9.22
    1,2,4-trichlorobenzene 12.36
    4-methylpyridine 40.65
    dibutyl ether 12.93
    2,6-dimethyl-4-heptanol 7.05
    DEF 58.84
    dimethyl isosorbide 42.62
    tetrachloroethylene 13.62
    eugenol 28.2
    triacetin 16.85
    span 80 17.74
    1,4-butanediol 15.89
    1,1-dichloroethane 10.84
    2-methyl-1-pentanol 13.7
    methyl formate 69.39
    2-methyl-1-butanol 15.14
    n-decane 2.03
    butyronitrile 18.58
    3,7-dimethyl-1-octanol 12.5
    1-chlorooctane 8.53
    1-chlorotetradecane 4.68
    n-nonane 1.57
    undecane 1.77
    tert-butylcyclohexane 0.72
    cyclooctane 0.29
    cyclopentanol 15.8
    tetrahydropyran 23.7
    tert-amyl methyl ether 14.96
    2,5,8-trioxanonane 60.52
    1-hexene 2.4
    2-isopropoxyethanol 26.08
    2,2,2-trifluoroethanol 10.11
    methyl butyrate 15.69

    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