2H-1,4-benzoxazin-3(4H)-one

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  • Identifiers

    CAS number
    5466-88-6

    Molecular formula
    C8H7NO2

    SMILES
    C1C(=O)NC2=CC=CC=C2O1

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 38.66%
    Nutty 32.52%
    Green 32.47%
    Caramellic 29.76%
    Burnt 29.35%
    Coumarinic 26.04%
    Phenolic 25.82%
    Fruity 25.03%
    Spicy 24.57%
    Roasted 23.11%

     

    Flavor
    Bitter 64.38%
    Sweet 51.08%
    Tonka 33.79%
    Coconut 33.44%
    Almond 28.63%
    Coumarin 26.44%
    Tobacco 24.28%
    Powdery 22.22%
    Caramel 22.21%
    Naphthalic 21.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    7.01 (neutral)

    Molecular weight
    149.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    306°C

    Flash point

    • 149.55 ˚C est.

  • Synonyms

    • 2H-1,4-Benzoxazin-3(4H)-one
    • 5466-88-6
    • 2H-1,4-Benzoxazin-3-one
    • 2H-benzo[b][1,4]oxazin-3(4H)-one
    • Q0QAF5G662
    • NSC-26354
    • DTXSID80203118
    • 2H-BENZO(B)(1,4)OXAZIN-3(4H)-ONE
    • RefChem:484114
    • DTXCID80125609
    • 2H-1,4-Benzoxazin-3(4H)-one (8CI)
    • 628-721-1
    • 4H-1,4-benzoxazin-3-one
    • MFCD00158536
    • 3-Oxo-4H-benzo[1,4]oxazine
    • 3,4-dihydro-2H-1,4-benzoxazin-3-one
    • NSC26354
    • 4-AZA-3-CHROMANONE
    • CHEMBL460153
    • 2H-1,4-BENZOXAZINE-3(4H)-ONE
    • 4h-benzo(1,4)oxazin-3-one
    • 4H-BENZO[1,4]OXAZIN-3-ONE
    • 2H,4H-benzo[e]1,4-oxazaperhydroin-3-one
    • NSC 26354
    • 1,4-benzoxazin-3-one
    • 2H-1,4-Benzoxazin-3(4H)-one (8CI)(9CI)
    • 2H-1,4-benzoxazin-3-ol
    • UNII-Q0QAF5G662
    • SCHEMBL56133
    • SCHEMBL56969
    • SCHEMBL75634
    • SCHEMBL88746
    • SCHEMBL341904
    • SCHEMBL533758
    • 4H-[1,4]benzoxazin-3-one
    • 4H-benzo[1.4]oxazin-3-one
    • orb3029369
    • SCHEMBL1340168
    • SCHEMBL1398550
    • 2H-[1,4]-benzoxazin-3-one
    • 2H-1,4 benzoxazine-3(4H)one
    • 2H-1,4-benzoxazin-3-(4H)one
    • ALBB-020505
    • (2H)1,4-benzoxazin-3(4H)-one
    • 2-H-1,4-benzoxazin-3-(4H)one
    • 2H-1,4-benzoxazin-3-(4H)-one
    • 2,3-dihydro-1,4-benzoxazin-3-one
    • 2H-1,4-Benzoxazin-3 (4H)-one
    • BDBM50438258
    • SBB016409
    • STK317993
    • STL301701
    • 3-Keto-4-aza-2,3-dihydrobenzopyran
    • AKOS000121575
    • AKOS016370878
    • AB04166
    • CS-W002455
    • FA53825
    • 3-oxo-2,3-dihydro-4H-1,4-benzoxazine
    • AC-23158
    • BP-10112
    • SY007578
    • 2H-1,4-Benzoxazin-3(4H)-one, 99%
    • 3,4-Dihydro-3-oxo-1,4(2H)-benzoxazine
    • DB-014112
    • B4553
    • ST45022695
    • EN300-17697
    • 2,3-DIHYDRO-3-OXO-4H-1,4-BENZOXAZINE
    • 1T-0333
    • AE-473/30224032
    • F303371
    • 3-OXO-3,4-DIHYDRO-2H-BENZO(B)(1,4)OXAZINE
    • Z56989567
    • F0918-7105
    • InChI=1/C8H7NO2/c10-8-5-11-7-4-2-1-3-6(7)9-8/h1-4H,5H2,(H,9,10
    • 5466-88-6

  • Applications

    2H-1,4-benzoxazin-3(4H)-one (CAS 5466-88-6) is regarded as an important organic chemical precursor, providing a heterocyclic core for the synthesis of benzoxazinone derivatives. It is commonly used as a building block in pharmaceutical research to assemble novel heterocycles and as a precursor scaffold for drug-like compounds. In agrochemical development, it is viewed as a scaffold for lead compounds to generate derivatives with crop-protection activity in the research stage. In the polymer and coatings sector, it can serve as a functionalized precursor for specialty materials and tailor-made coatings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 27.17
    methanol 53.99
    isopropanol 20.39
    water 6.44
    ethyl acetate 47.57
    n-propanol 21.06
    acetone 139.49
    n-butanol 17.23
    acetonitrile 87.94
    DMF 315.47
    toluene 8.28
    isobutanol 16.56
    1,4-dioxane 154.59
    methyl acetate 76.14
    THF 120.56
    2-butanone 77.47
    n-pentanol 20.49
    sec-butanol 17.37
    n-hexane 0.57
    ethylene glycol 43.99
    NMP 215.49
    cyclohexane 0.67
    DMSO 671.65
    n-butyl acetate 31.38
    n-octanol 17.43
    chloroform 41.93
    n-propyl acetate 38.66
    acetic acid 73.84
    dichloromethane 77.24
    cyclohexanone 78.92
    propylene glycol 20.34
    isopropyl acetate 27.36
    DMAc 267.82
    2-ethoxyethanol 83.35
    isopentanol 20.31
    n-heptane 2.0
    ethyl formate 45.53
    1,2-dichloroethane 61.23
    n-hexanol 20.18
    2-methoxyethanol 114.72
    isobutyl acetate 22.5
    tetrachloromethane 4.8
    n-pentyl acetate 21.41
    transcutol 291.5
    n-heptanol 13.7
    ethylbenzene 7.1
    MIBK 32.62
    2-propoxyethanol 64.05
    tert-butanol 35.02
    MTBE 23.64
    2-butoxyethanol 39.78
    propionic acid 40.49
    o-xylene 11.03
    formic acid 64.81
    diethyl ether 23.83
    m-xylene 10.54
    p-xylene 11.47
    chlorobenzene 20.48
    dimethyl carbonate 43.55
    n-octane 1.22
    formamide 125.4
    cyclopentanone 129.86
    2-pentanone 47.95
    anisole 33.82
    cyclopentyl methyl ether 37.05
    gamma-butyrolactone 161.18
    1-methoxy-2-propanol 66.72
    pyridine 60.81
    3-pentanone 43.33
    furfural 148.57
    n-dodecane 1.7
    diethylene glycol 95.18
    diisopropyl ether 8.21
    tert-amyl alcohol 25.63
    acetylacetone 86.13
    n-hexadecane 1.9
    acetophenone 43.23
    methyl propionate 53.28
    isopentyl acetate 28.38
    trichloroethylene 99.9
    n-nonanol 16.31
    cyclohexanol 17.3
    benzyl alcohol 30.31
    2-ethylhexanol 15.88
    isooctanol 12.9
    dipropyl ether 19.48
    1,2-dichlorobenzene 23.87
    ethyl lactate 31.36
    propylene carbonate 63.8
    n-methylformamide 115.64
    2-pentanol 13.1
    n-pentane 0.56
    1-propoxy-2-propanol 41.66
    1-methoxy-2-propyl acetate 44.62
    2-(2-methoxypropoxy) propanol 57.87
    mesitylene 7.9
    ε-caprolactone 64.39
    p-cymene 10.2
    epichlorohydrin 159.76
    1,1,1-trichloroethane 27.87
    2-aminoethanol 35.56
    morpholine-4-carbaldehyde 215.64
    sulfolane 211.24
    2,2,4-trimethylpentane 1.13
    2-methyltetrahydrofuran 66.29
    n-hexyl acetate 32.76
    isooctane 1.02
    2-(2-butoxyethoxy)ethanol 75.1
    sec-butyl acetate 23.49
    tert-butyl acetate 31.11
    decalin 1.45
    glycerin 56.76
    diglyme 157.39
    acrylic acid 49.42
    isopropyl myristate 16.61
    n-butyric acid 36.11
    acetyl acetate 38.25
    di(2-ethylhexyl) phthalate 19.24
    ethyl propionate 34.59
    nitromethane 253.07
    1,2-diethoxyethane 57.92
    benzonitrile 40.26
    trioctyl phosphate 14.88
    1-bromopropane 14.7
    gamma-valerolactone 173.15
    n-decanol 13.56
    triethyl phosphate 22.3
    4-methyl-2-pentanol 12.22
    propionitrile 42.07
    vinylene carbonate 61.06
    1,1,2-trichlorotrifluoroethane 89.26
    DMS 47.35
    cumene 7.74
    2-octanol 10.57
    2-hexanone 39.6
    octyl acetate 21.09
    limonene 12.88
    1,2-dimethoxyethane 134.56
    ethyl orthosilicate 19.68
    tributyl phosphate 19.05
    diacetone alcohol 50.34
    N,N-dimethylaniline 27.5
    acrylonitrile 70.83
    aniline 20.26
    1,3-propanediol 41.65
    bromobenzene 17.1
    dibromomethane 30.65
    1,1,2,2-tetrachloroethane 63.27
    2-methyl-cyclohexyl acetate 25.32
    tetrabutyl urea 29.32
    diisobutyl methanol 11.99
    2-phenylethanol 28.4
    styrene 8.39
    dioctyl adipate 27.36
    dimethyl sulfate 100.98
    ethyl butyrate 30.15
    methyl lactate 42.0
    butyl lactate 24.95
    diethyl carbonate 25.77
    propanediol butyl ether 46.32
    triethyl orthoformate 24.98
    p-tert-butyltoluene 9.44
    methyl 4-tert-butylbenzoate 39.3
    morpholine 113.71
    tert-butylamine 14.66
    n-dodecanol 11.55
    dimethoxymethane 107.43
    ethylene carbonate 48.81
    cyrene 61.18
    2-ethoxyethyl acetate 42.61
    2-ethylhexyl acetate 22.23
    1,2,4-trichlorobenzene 30.91
    4-methylpyridine 48.17
    dibutyl ether 19.67
    2,6-dimethyl-4-heptanol 11.99
    DEF 74.69
    dimethyl isosorbide 90.11
    tetrachloroethylene 35.83
    eugenol 42.25
    triacetin 51.45
    span 80 35.63
    1,4-butanediol 29.66
    1,1-dichloroethane 35.41
    2-methyl-1-pentanol 21.19
    methyl formate 111.61
    2-methyl-1-butanol 17.19
    n-decane 2.24
    butyronitrile 31.97
    3,7-dimethyl-1-octanol 18.29
    1-chlorooctane 9.7
    1-chlorotetradecane 5.25
    n-nonane 1.89
    undecane 1.94
    tert-butylcyclohexane 1.62
    cyclooctane 0.55
    cyclopentanol 24.61
    tetrahydropyran 48.03
    tert-amyl methyl ether 20.92
    2,5,8-trioxanonane 111.09
    1-hexene 3.33
    2-isopropoxyethanol 54.33
    2,2,2-trifluoroethanol 51.02
    methyl butyrate 45.28

    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