Isatoic Anhydride

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  • Identifiers

    CAS number
    118-48-9

    Molecular formula
    C8H5NO3

    SMILES
    C1=CC=C2C(=C1)C(=O)OC(=O)N2

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 43.23%
    Sweet 38.17%
    Burnt 33.46%
    Nutty 32.76%
    Bitter 28.61%
    Balsamic 28.05%
    Coumarinic 27.55%
    Coconut 24.77%
    Phenolic 24.27%
    Powdery 23.25%

     

    Flavor
    Bitter 75.79%
    Sweet 30.85%
    Balsam 27.87%
    Tonka 24.97%
    Odorless 21.05%
    Urine 20.95%
    Almond 20.43%
    Green 20.36%
    Red hots 19.84%
    Almond shell 19.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    8.13 (weak base)

    Molecular weight
    163.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    383°C

    Melting point expt.

    • 243 °C WITH DECOMPOSITION

    Flash point

    • 190.49 ˚C est.

    Solubility expt.

    • MISCIBLE IN WATER, HOT ALC, AND ACETONE; INSOL IN ETHER, BENZENE, AND CHLOROFORM

  • Synonyms

    • Isatoic anhydride
    • 118-48-9
    • 2H-3,1-Benzoxazine-2,4(1H)-dione
    • 4H-3,1-Benzoxazine-2,4(1H)-dione
    • ISATOIC ACID ANHYDRIDE
    • N-Carboxyanthranilic anhydride
    • 3,1-Benzoxazine-2,4(1H)-dione
    • Anthranilic acid, N-carboxy-, cyclic anhydride
    • Benzoic acid, 2-(carboxyamino)-, cyclic anhydride
    • R8TFA74Y4U
    • 2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
    • DTXSID6026955
    • 1,2-dihydro-3,1-benzoxazine-2,4-dione
    • NSC-29555
    • 1h-benz(d)(1,3)oxazine-2,4-dione
    • NSC-104662
    • DTXCID906955
    • 2,4-dioxo-1,2-dihydro-4h-3,1-benzoxazine
    • RefChem:791499
    • 204-255-0
    • 1H-Benzo[d][1,3]oxazine-2,4-dione
    • 1H-3,1-benzoxazine-2,4-dione
    • Isato acid anhydride
    • MFCD00006700
    • CHEMBL346059
    • 2H-3,4(1H)-dione
    • Anthranilic acid, cyclic anhydride
    • benzo[d]1,3-oxazine-2,4-dione
    • CAS-118-48-9
    • HSDB 5017
    • EINECS 204-255-0
    • UNII-R8TFA74Y4U
    • NSC 104662
    • BRN 0136786
    • AI3-24983
    • Isatoic anhydrid
    • Anthranilic acid N-carboxylic acid anhydride
    • Isatoic anhydride, 96%
    • 1,2-Dihydro-4H-3,1-benzoxazine-2,4-dione
    • EC 204-255-0
    • NCIOpen2_002029
    • SCHEMBL16251
    • ISATOIC ACID,ANHYDRIDE
    • 4-27-00-03330 (Beilstein Handbook Reference)
    • Isatoic anhydride treated BSA
    • SCHEMBL2075656
    • SCHEMBL5536755
    • SCHEMBL29669800
    • 2,4-dioxo-1H-3,1-benzoxazine
    • HMS1607F14
    • 1H-[3,1]benzoxazine-2,4-dione
    • BB_NC-00461
    • CS-M0780
    • NSC29555
    • Tox21_201325
    • Tox21_303058
    • 3,1-Benzoxazin-2,4-(1H)-dione
    • BBL009904
    • BDBM50201570
    • EBC-03346
    • NSC104662
    • SBB003928
    • STK711078
    • 1h-benzo[d][1,3]oxazine-2,4dione
    • 2H-3,1-benzoxazine-2,4(1H)dione
    • ISATOIC ACID ANHYDRIDE [HSDB]
    • AKOS000120179
    • 1H-benzo[d][1,3]oxazin-2,4-dione
    • AC-3291
    • DB11593
    • FI01742
    • FS-3311
    • s12335
    • 2H-3,1-benzoxazine-2,4-(1H)-dione
    • NCGC00164009-01
    • NCGC00164009-02
    • NCGC00257195-01
    • NCGC00258877-01
    • BP-10896
    • HY-76222
    • DB-041408
    • 2H-benzo[d][1,3]oxazine-2,4(1H)-dione
    • I0081
    • NS00006862
    • ST50330601
    • EN300-19149
    • Isatoic anhydride, technical, >=94% (HPLC)
    • 118I489
    • AE-641/30105041
    • F091215
    • Q11286492
    • F0036-0953
    • Z104472968
    • InChI=1/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11
    • 118-48-9

  • Applications

    Isatoic anhydride is a versatile organic intermediate used to access nitrogen-containing heterocycles and amide derivatives. In pharmaceutical research, it serves as a convenient starting material for indole- and quinazolinone-type scaffolds and for preparing anthranilamide derivatives that underpin drug-like molecules. In industrial manufacturing, it is a key precursor for dye and pigment intermediates and for functionalized monomers in polymers and coatings. It also functions as a reactive partner for attaching the anthraniloyl moiety to amines, enabling library generation and the synthesis of specialty reagents. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.23
    methanol 8.63
    isopropanol 3.44
    water 0.09
    ethyl acetate 7.66
    n-propanol 3.92
    acetone 22.21
    n-butanol 3.94
    acetonitrile 11.4
    DMF 122.46
    toluene 0.43
    isobutanol 2.93
    1,4-dioxane 14.89
    methyl acetate 13.66
    THF 48.06
    2-butanone 17.24
    n-pentanol 3.46
    sec-butanol 3.64
    n-hexane 0.02
    ethylene glycol 5.92
    NMP 90.78
    cyclohexane 0.02
    DMSO 214.48
    n-butyl acetate 7.18
    n-octanol 2.34
    chloroform 0.46
    n-propyl acetate 5.21
    acetic acid 9.38
    dichloromethane 1.72
    cyclohexanone 11.58
    propylene glycol 4.85
    isopropyl acetate 4.58
    DMAc 88.28
    2-ethoxyethanol 18.22
    isopentanol 4.67
    n-heptane 0.08
    ethyl formate 6.59
    1,2-dichloroethane 3.4
    n-hexanol 3.73
    2-methoxyethanol 45.94
    isobutyl acetate 2.73
    tetrachloromethane 0.09
    n-pentyl acetate 5.37
    transcutol 48.86
    n-heptanol 2.76
    ethylbenzene 0.44
    MIBK 6.22
    2-propoxyethanol 21.62
    tert-butanol 6.46
    MTBE 3.43
    2-butoxyethanol 12.88
    propionic acid 6.47
    o-xylene 0.64
    formic acid 9.04
    diethyl ether 2.41
    m-xylene 0.56
    p-xylene 0.64
    chlorobenzene 0.87
    dimethyl carbonate 10.66
    n-octane 0.05
    formamide 26.87
    cyclopentanone 33.07
    2-pentanone 10.27
    anisole 4.07
    cyclopentyl methyl ether 6.72
    gamma-butyrolactone 41.32
    1-methoxy-2-propanol 26.45
    pyridine 8.57
    3-pentanone 6.49
    furfural 32.41
    n-dodecane 0.1
    diethylene glycol 24.62
    diisopropyl ether 0.65
    tert-amyl alcohol 5.68
    acetylacetone 16.95
    n-hexadecane 0.12
    acetophenone 6.5
    methyl propionate 12.29
    isopentyl acetate 6.71
    trichloroethylene 4.35
    n-nonanol 2.57
    cyclohexanol 2.39
    benzyl alcohol 4.72
    2-ethylhexanol 2.85
    isooctanol 2.38
    dipropyl ether 2.95
    1,2-dichlorobenzene 1.35
    ethyl lactate 6.5
    propylene carbonate 14.59
    n-methylformamide 33.83
    2-pentanol 2.24
    n-pentane 0.02
    1-propoxy-2-propanol 13.68
    1-methoxy-2-propyl acetate 13.54
    2-(2-methoxypropoxy) propanol 18.06
    mesitylene 0.41
    ε-caprolactone 12.95
    p-cymene 1.15
    epichlorohydrin 44.49
    1,1,1-trichloroethane 1.1
    2-aminoethanol 7.53
    morpholine-4-carbaldehyde 55.05
    sulfolane 75.76
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 16.59
    n-hexyl acetate 6.61
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 22.11
    sec-butyl acetate 3.48
    tert-butyl acetate 6.7
    decalin 0.08
    glycerin 13.73
    diglyme 40.76
    acrylic acid 8.14
    isopropyl myristate 3.2
    n-butyric acid 6.81
    acetyl acetate 5.06
    di(2-ethylhexyl) phthalate 4.95
    ethyl propionate 5.79
    nitromethane 50.77
    1,2-diethoxyethane 8.28
    benzonitrile 4.63
    trioctyl phosphate 3.7
    1-bromopropane 0.79
    gamma-valerolactone 45.08
    n-decanol 2.14
    triethyl phosphate 4.7
    4-methyl-2-pentanol 1.85
    propionitrile 6.17
    vinylene carbonate 10.22
    1,1,2-trichlorotrifluoroethane 19.6
    DMS 10.03
    cumene 0.59
    2-octanol 1.71
    2-hexanone 6.81
    octyl acetate 4.52
    limonene 1.45
    1,2-dimethoxyethane 30.82
    ethyl orthosilicate 3.77
    tributyl phosphate 4.18
    diacetone alcohol 16.81
    N,N-dimethylaniline 3.79
    acrylonitrile 12.27
    aniline 2.27
    1,3-propanediol 11.91
    bromobenzene 0.57
    dibromomethane 0.64
    1,1,2,2-tetrachloroethane 3.65
    2-methyl-cyclohexyl acetate 5.25
    tetrabutyl urea 7.5
    diisobutyl methanol 2.05
    2-phenylethanol 5.63
    styrene 0.46
    dioctyl adipate 5.73
    dimethyl sulfate 28.83
    ethyl butyrate 5.5
    methyl lactate 13.78
    butyl lactate 7.02
    diethyl carbonate 4.46
    propanediol butyl ether 11.62
    triethyl orthoformate 4.65
    p-tert-butyltoluene 1.04
    methyl 4-tert-butylbenzoate 9.93
    morpholine 21.01
    tert-butylamine 1.85
    n-dodecanol 1.69
    dimethoxymethane 35.27
    ethylene carbonate 7.44
    cyrene 18.71
    2-ethoxyethyl acetate 11.45
    2-ethylhexyl acetate 4.85
    1,2,4-trichlorobenzene 2.49
    4-methylpyridine 7.57
    dibutyl ether 2.31
    2,6-dimethyl-4-heptanol 2.05
    DEF 18.63
    dimethyl isosorbide 29.43
    tetrachloroethylene 1.54
    eugenol 11.74
    triacetin 9.13
    span 80 10.29
    1,4-butanediol 5.08
    1,1-dichloroethane 1.16
    2-methyl-1-pentanol 4.13
    methyl formate 24.15
    2-methyl-1-butanol 4.24
    n-decane 0.12
    butyronitrile 5.24
    3,7-dimethyl-1-octanol 2.71
    1-chlorooctane 0.7
    1-chlorotetradecane 0.47
    n-nonane 0.08
    undecane 0.11
    tert-butylcyclohexane 0.09
    cyclooctane 0.01
    cyclopentanol 5.3
    tetrahydropyran 5.07
    tert-amyl methyl ether 3.84
    2,5,8-trioxanonane 31.17
    1-hexene 0.22
    2-isopropoxyethanol 10.21
    2,2,2-trifluoroethanol 5.72
    methyl butyrate 7.67

    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