2,2'-(1,4-Phenylene)bis(3,1-benzoxazin-4-one)

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  • Identifiers

    CAS number
    18600-59-4

    Molecular formula
    C22H12N2O4

    SMILES
    C1=CC=C2C(=C1)C(=O)OC(=N2)C3=CC=C(C=C3)C4=NC5=CC=CC=C5C(=O)O4

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 52.66%
    Floral 45.33%
    Coumarinic 38.95%
    Powdery 34.48%
    Animal 34.35%
    Balsamic 34.21%
    Bitter 33.49%
    Phenolic 33.49%
    Nutty 32.33%
    Burnt 29.74%

     

    Flavor
    Bitter 95.8%
    Very strong 19.96%
    Indole 19.61%
    Moth ball 19.54%
    Naphthelene 19.14%
    Nitrile 18.86%
    Odorless 18.84%
    Cereal 18.5%
    Bread crust 18.46%
    Cedarleaf 18.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    5.66 (weak acid)

    Molecular weight
    368.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1134°C

    Flash point

    • 269.4 ˚C est.

  • Synonyms

    • 18600-59-4
    • 4H-3,1-Benzoxazin-4-one, 2,2'-(1,4-phenylene)bis-
    • 2,2'-(1,4-Phenylene)bis(4H-3,1-benzoxazin-4-one)
    • 8V348NL4QK
    • 2,2'-(1,4-Phenylene)bis(3,1-benzoxazin-4-one)
    • DTXSID40864845
    • PIONIN ZA 101
    • CYASORB UV 3638
    • EC 418-280-1
    • 2,2-(1,4-phenylene)bis((4H-3,1-benzoxazine-4-one)
    • 2,2'-(1,4-phenylene)bis[4h-3,1-benzoxazin-4-one]
    • 4H-3,1-BENZOXAZIN-4-ONE, 2,2'-P-PHENYLENEBIS-
    • RefChem:440114
    • DTXCID40813318
    • 418-280-1
    • 2,2'-(1,4-Phenylene)bis(4H-benzo[d][1,3]oxazin-4-one)
    • Cyasorb UV-3638
    • 2,2'-(1,4-PHENYLENE)BIS-4H-3,1-BENZOXAZIN-4-ONE
    • MFCD00356293
    • 2-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one
    • 2,2/'-(1,4-PHENYLENE)BIS-4H-3,1-BENZOXAZIN-4-ONE
    • UNII-8V348NL4QK
    • 2,2'-benzene-1,4-diylbis(4H-3,1-benzoxazin-4-one)
    • BAS 00298026
    • Oprea1_802650
    • Oprea1_828724
    • SCHEMBL125184
    • SCHEMBL29456973
    • MSK162081
    • STK296324
    • AKOS000640593
    • AS-10722
    • SY237771
    • CS-0206775
    • NS00003546
    • P2656
    • ST50222003
    • 2,2'-p-phenylenebis(3,1-benzoxazin-4-one)
    • 2,2'-p-phenylenebis(3, 1-benzoxazin-4-one)
    • A11232
    • Phenylene-1,4-bis-(benz-1,3-oxazin-4-one)
    • 600P594
    • 2,2'-(1,4-Phenylene)di(4H-3,1-benzoxazin-4-one)
    • 2,2-(1,4-Phenylene)bis-4H-3,1-benzoxazin-4-one
    • Q27271051
    • 2,2''-(1,4-Phenylene)bis-4H-3,1-benzoxazin-4-one
    • 2,2'-(1,4-PHENYLENE)BIS[4H-3,1-BENZOXAZIN-4-ONE
    • 2-[4-(4-oxobenzo[d]1,3-oxazin-2-yl)phenyl]benzo[d]1,3-oxazin-4-one
    • 2,2'-(1,4-Phenylene)bis(4H-3,1-benzoxazin-4-one) 100 microg/mL in Chloroform:Acetonitrile
    • 18600-59-4

  • Applications

    2,2'-(1,4-Phenylene)bis(3,1-benzoxazin-4-one) (CAS 18600-59-4) is typically used as a latent curing agent for epoxy resins, releasing active amine functionality upon heating to drive crosslinking in coatings, adhesives, and composite systems. It acts as a difunctional crosslinker in thermoset polymer formulations to enhance thermal stability and chemical resistance of coatings, laminates, and electronics packaging. The compound is commonly employed as a reactive intermediate in the formulation of specialty resins and high-performance polymers. In electronics and advanced coatings, it may be chosen for controlled cure kinetics and compatibility with epoxy systems. Depending on the formulation, it is used within industrial manufacturing where precise curing behavior and performance tuning of epoxy-based materials are needed.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.05
    methanol 0.04
    isopropanol 0.05
    water 0.0
    ethyl acetate 0.18
    n-propanol 0.08
    acetone 0.18
    n-butanol 0.09
    acetonitrile 0.08
    DMF 0.39
    toluene 0.31
    isobutanol 0.06
    1,4-dioxane 0.53
    methyl acetate 0.18
    THF 1.46
    2-butanone 0.5
    n-pentanol 0.11
    sec-butanol 0.1
    n-hexane 0.01
    ethylene glycol 0.01
    NMP 0.52
    cyclohexane 0.01
    DMSO 0.44
    n-butyl acetate 0.32
    n-octanol 0.15
    chloroform 0.2
    n-propyl acetate 0.2
    acetic acid 0.1
    dichloromethane 0.41
    cyclohexanone 0.7
    propylene glycol 0.02
    isopropyl acetate 0.17
    DMAc 1.31
    2-ethoxyethanol 0.27
    isopentanol 0.12
    n-heptane 0.02
    ethyl formate 0.16
    1,2-dichloroethane 0.34
    n-hexanol 0.13
    2-methoxyethanol 0.32
    isobutyl acetate 0.13
    tetrachloromethane 0.02
    n-pentyl acetate 0.55
    transcutol 1.56
    n-heptanol 0.17
    ethylbenzene 0.17
    MIBK 0.27
    2-propoxyethanol 0.5
    tert-butanol 0.05
    MTBE 0.13
    2-butoxyethanol 0.55
    propionic acid 0.1
    o-xylene 0.2
    formic acid 0.06
    diethyl ether 0.18
    m-xylene 0.16
    p-xylene 0.22
    chlorobenzene 0.14
    dimethyl carbonate 0.11
    n-octane 0.02
    formamide 0.12
    cyclopentanone 0.73
    2-pentanone 0.32
    anisole 0.23
    cyclopentyl methyl ether 0.27
    gamma-butyrolactone 0.53
    1-methoxy-2-propanol 0.23
    pyridine 1.18
    3-pentanone 0.31
    furfural 0.78
    n-dodecane 0.02
    diethylene glycol 0.22
    diisopropyl ether 0.06
    tert-amyl alcohol 0.12
    acetylacetone 0.36
    n-hexadecane 0.03
    acetophenone 0.4
    methyl propionate 0.18
    isopentyl acetate 0.41
    trichloroethylene 0.66
    n-nonanol 0.21
    cyclohexanol 0.11
    benzyl alcohol 0.23
    2-ethylhexanol 0.16
    isooctanol 0.17
    dipropyl ether 0.24
    1,2-dichlorobenzene 0.15
    ethyl lactate 0.13
    propylene carbonate 0.22
    n-methylformamide 0.14
    2-pentanol 0.07
    n-pentane 0.01
    1-propoxy-2-propanol 0.37
    1-methoxy-2-propyl acetate 0.44
    2-(2-methoxypropoxy) propanol 0.73
    mesitylene 0.09
    ε-caprolactone 0.54
    p-cymene 0.19
    epichlorohydrin 1.08
    1,1,1-trichloroethane 0.08
    2-aminoethanol 0.03
    morpholine-4-carbaldehyde 0.64
    sulfolane 0.71
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.5
    n-hexyl acetate 0.47
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 0.89
    sec-butyl acetate 0.19
    tert-butyl acetate 0.22
    decalin 0.01
    glycerin 0.05
    diglyme 1.89
    acrylic acid 0.1
    isopropyl myristate 0.3
    n-butyric acid 0.18
    acetyl acetate 0.1
    di(2-ethylhexyl) phthalate 0.34
    ethyl propionate 0.2
    nitromethane 0.23
    1,2-diethoxyethane 0.88
    benzonitrile 0.29
    trioctyl phosphate 0.21
    1-bromopropane 0.19
    gamma-valerolactone 1.17
    n-decanol 0.16
    triethyl phosphate 0.24
    4-methyl-2-pentanol 0.07
    propionitrile 0.13
    vinylene carbonate 0.24
    1,1,2-trichlorotrifluoroethane 0.47
    DMS 0.33
    cumene 0.13
    2-octanol 0.15
    2-hexanone 0.41
    octyl acetate 0.31
    limonene 0.17
    1,2-dimethoxyethane 0.87
    ethyl orthosilicate 0.26
    tributyl phosphate 0.26
    diacetone alcohol 0.33
    N,N-dimethylaniline 0.24
    acrylonitrile 0.2
    aniline 0.22
    1,3-propanediol 0.09
    bromobenzene 0.14
    dibromomethane 0.2
    1,1,2,2-tetrachloroethane 0.44
    2-methyl-cyclohexyl acetate 0.29
    tetrabutyl urea 0.55
    diisobutyl methanol 0.14
    2-phenylethanol 0.37
    styrene 0.15
    dioctyl adipate 0.41
    dimethyl sulfate 0.18
    ethyl butyrate 0.29
    methyl lactate 0.12
    butyl lactate 0.42
    diethyl carbonate 0.18
    propanediol butyl ether 0.26
    triethyl orthoformate 0.34
    p-tert-butyltoluene 0.15
    methyl 4-tert-butylbenzoate 0.73
    morpholine 0.55
    tert-butylamine 0.03
    n-dodecanol 0.13
    dimethoxymethane 0.38
    ethylene carbonate 0.18
    cyrene 0.44
    2-ethoxyethyl acetate 0.78
    2-ethylhexyl acetate 0.36
    1,2,4-trichlorobenzene 0.22
    4-methylpyridine 0.63
    dibutyl ether 0.45
    2,6-dimethyl-4-heptanol 0.14
    DEF 0.48
    dimethyl isosorbide 1.28
    tetrachloroethylene 0.34
    eugenol 0.77
    triacetin 0.44
    span 80 0.51
    1,4-butanediol 0.04
    1,1-dichloroethane 0.1
    2-methyl-1-pentanol 0.18
    methyl formate 0.12
    2-methyl-1-butanol 0.13
    n-decane 0.04
    butyronitrile 0.15
    3,7-dimethyl-1-octanol 0.19
    1-chlorooctane 0.15
    1-chlorotetradecane 0.07
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.1
    tetrahydropyran 0.38
    tert-amyl methyl ether 0.2
    2,5,8-trioxanonane 1.48
    1-hexene 0.07
    2-isopropoxyethanol 0.22
    2,2,2-trifluoroethanol 0.04
    methyl butyrate 0.28

    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