4,4'-Diaminodiphenyl Ether

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  • Identifiers

    CAS number
    101-80-4

    Molecular formula
    C12H12N2O

    SMILES
    C1=CC(=CC=C1N)OC2=CC=C(C=C2)N

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 45.93%
    Sweet 45.92%
    Fruity 43.64%
    Phenolic 41.78%
    Animal 39.25%
    Grape 33.1%
    Burnt 28.0%
    Meaty 27.54%
    Smoky 24.64%
    Powdery 23.84%

     

    Flavor
    Phenolic 51.59%
    Sweet 40.36%
    Fruity 36.01%
    Medicinal 31.43%
    Mild 30.46%
    Bitter 28.09%
    Meaty 28.05%
    Floral 25.53%
    Animal 23.62%
    Sulfurous 22.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    5.58 (weak acid)

    Molecular weight
    200.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 367 to 369 °F (NTP, 1992)
    • 189 °C (decomposes

    Boiling point

    • Sublimes (NTP, 1992)
    • >300 °C

    Flash point

    • 215.86 ˚C est.
    • 426 °F (NTP, 1992)
    • 219 °C
    • 219 °C (closed cup)

    Solubility expt.

    • less than 0.1 mg/mL at 59 °F (NTP, 1992)
    • Insoluble in water, benzene, carbon tetrachloride and ethanol; soluble in acetone

  • Synonyms

    • 4,4'-Oxydianiline
    • 101-80-4
    • 4,4'-Diaminodiphenyl ether
    • 4,4-Oxydianiline
    • 4-Aminophenyl ether
    • 4-(4-aminophenoxy)aniline
    • Oxydianiline
    • Diaminodiphenyl ether
    • 4,4'-Oxybisbenzenamine
    • Bis(4-aminophenyl) ether
    • Benzenamine, 4,4'-oxybis-
    • Bis(p-aminophenyl) ether
    • Dadpe
    • p,p'-Oxydianiline
    • p-Aminophenyl ether
    • 4,4-Diaminodiphenyl ether
    • p,p'-Oxybis(aniline)
    • 4,4'-Oxydiphenylamine
    • Oxydi-p-phenylenediamine
    • Aniline, 4,4'-oxydi-
    • p,p'-Diaminodiphenyl ether
    • 4,4'-Diaminobiphenyl oxide
    • 4,4'-Diaminodiphenyl oxide
    • Oxybis(4-aminobenzene)
    • Bis(4-aminophenyl)ether
    • Di-(4-aminophenyl)ether
    • 4,4'-Diaminophenyl oxide
    • 4,4'-Oxybisaniline
    • 4,4'-DIAMINOPHENYL ETHER
    • NCI-C50146
    • Bis(p-aminophenyl)ether
    • EINECS 202-977-0
    • 4,4'-Diaminobiphenyloxide
    • CCRIS 491
    • Ether, 4,4'-diaminodiphenyl
    • 4,4-Dadpe
    • 4-(4-Aminophenoxy)phenylamine
    • DTXSID0021094
    • HSDB 1316
    • 4-aminophenylether
    • UNII-28DLB4Z70T
    • NSC 37075
    • BRN 0475735
    • AI3-18375
    • NSC-6089
    • di(4-Aminophenyl) ether
    • DPE (AMINE)
    • MFCD00007863
    • NSC-37075
    • P-DIAMINODIPHENYLETHER
    • 4,4'-Oxydianiline (ODA)
    • 28DLB4Z70T
    • DTXCID401094
    • Ether, 4,4'-diaminodiphenyl-
    • 121509-79-3
    • CHEBI:34384
    • NSC6089
    • EC 202-977-0
    • 4,4'-OXYBIS(BENZENAMINE)
    • 4-13-00-01038 (Beilstein Handbook Reference)
    • NSC37075
    • Aniline,4'-oxydi-
    • 4-Aminophenylether (4,4'-Oxydianiline)
    • BIS(4-AMINOPHENYL) ETHER [HSDB]
    • Oxybis[4-aminobenzene]
    • Benzenamine,4'-oxybis-
    • 1-AMINO-4-(4-AMINOPHENOXY)BENZENE
    • 4,4'-DIAMINODIPHENYL ETHER [IARC]
    • 4,4'-Oxybis(aniline)
    • 4,4'-Oxybis[aniline]
    • WLN: ZR DOR DZ
    • Ether,4'-diaminodiphenyl-
    • 4,4'-Oxydianiline, 97%
    • CAS-101-80-4
    • 4,4'-DIAMINODIPHENYL ETHER (IARC)
    • 4,4'-ODA
    • 4,4'diaminodiphenylether
    • 4,4'-diaminodiphenyloxide
    • p,p'Oxydianiline
    • 4,4Oxydianiline
    • pAminophenyl ether
    • 4Aminophenyl ether
    • 4,4'Oxybisaniline
    • Oxydipphenylenediamine
    • p,p'Oxybis(aniline)
    • Di(4aminophenyl)ether
    • Oxybis(4aminobenzene)
    • 4,4'Oxydiphenylamine
    • Bis(paminophenyl)ether
    • 4,4'Oxybisbenzenamine
    • 4,4\'-Oxydianiline
    • Aniline, 4,4'oxydi
    • Bis(4aminophenyl)ether
    • Bis(paminophenyl) ether
    • bis(4aminophenyl) ether
    • 4,4'-Oxydiphenylalamine
    • 4,4'Diaminobiphenyloxide
    • 4,4'Diaminophenyl ether
    • 4,4'Diaminophenyl oxide
    • 4,4Diaminodiphenyl ether
    • p,p'Diaminodiphenyl ether
    • Benzenamine, 4,4'oxybis
    • CBMicro_028442
    • 4,4'diaminodiphenyl oxide
    • 4,4'Diaminobiphenyl oxide
    • Cambridge id 5493582
    • 4,4'-biaminodiphenyl ether
    • 4,4'-diaminobiphenyl ether
    • Ether, 4,4'diaminodiphenyl
    • Oprea1_332864
    • Oprea1_805797
    • SCHEMBL41849
    • YSWG195
    • BIDD:ER0256
    • 4,4 inverted exclamation marka-Diaminodiphenyl ether
    • 4,4'-DADPE
    • CHEMBL354663
    • 4-(4-Aminophenoxy)phenylamine #
    • 4,4'-Diaminodiphenyl ether (ODA)
    • Tox21_202035
    • Tox21_300133
    • BBL012119
    • STK046240
    • AKOS000118817
    • CCG-105139
    • CS-W015612
    • PS-5282
    • 4,4'-Oxydianiline, analytical standard

  • Applications

    4,4'-Diaminodiphenyl Ether, CAS 101-80-4, is an aromatic diamine used primarily as a building block and curing agent in high-performance polymers and engineering plastics, notably polyimides and related polyurethanes, to enhance thermal stability and mechanical properties. It also serves as a curing agent for epoxy resin systems, enabling crosslinking and improved heat resistance in coatings and adhesive formulations. In coatings and inks, it contributes to high-performance epoxy and polyimide formulations intended for protective coatings and electronic applications. In electronics and electrical insulation, polymers derived from it provide dielectric properties and dimensional stability suitable for advanced devices. As an industrial intermediate, it is used in the synthesis of specialty polymers and other advanced materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 26.13
    methanol 66.41
    isopropanol 19.08
    water 3.98
    ethyl acetate 134.78
    n-propanol 25.84
    acetone 132.63
    n-butanol 19.08
    acetonitrile 166.42
    DMF 358.37
    toluene 4.28
    isobutanol 11.21
    1,4-dioxane 155.55
    methyl acetate 164.56
    THF 295.38
    2-butanone 98.93
    n-pentanol 19.81
    sec-butanol 15.73
    n-hexane 0.63
    ethylene glycol 43.26
    NMP 54.07
    cyclohexane 0.51
    DMSO 617.12
    n-butyl acetate 37.12
    n-octanol 5.68
    chloroform 82.92
    n-propyl acetate 56.24
    acetic acid 146.38
    dichloromethane 44.94
    cyclohexanone 45.71
    propylene glycol 45.44
    isopropyl acetate 46.47
    DMAc 317.51
    2-ethoxyethanol 143.36
    isopentanol 14.07
    n-heptane 1.0
    ethyl formate 124.24
    1,2-dichloroethane 41.19
    n-hexanol 15.32
    2-methoxyethanol 174.39
    isobutyl acetate 24.02
    tetrachloromethane 7.36
    n-pentyl acetate 12.4
    transcutol 174.21
    n-heptanol 8.28
    ethylbenzene 4.37
    MIBK 21.91
    2-propoxyethanol 80.63
    tert-butanol 30.43
    MTBE 31.27
    2-butoxyethanol 37.27
    propionic acid 75.69
    o-xylene 4.4
    formic acid 113.71
    diethyl ether 33.87
    m-xylene 3.59
    p-xylene 6.36
    chlorobenzene 14.29
    dimethyl carbonate 108.15
    n-octane 0.44
    formamide 251.91
    cyclopentanone 116.31
    2-pentanone 47.83
    anisole 38.87
    cyclopentyl methyl ether 23.72
    gamma-butyrolactone 202.44
    1-methoxy-2-propanol 99.64
    pyridine 72.03
    3-pentanone 47.71
    furfural 187.79
    n-dodecane 0.46
    diethylene glycol 107.02
    diisopropyl ether 6.16
    tert-amyl alcohol 20.4
    acetylacetone 122.08
    n-hexadecane 0.49
    acetophenone 35.07
    methyl propionate 111.36
    isopentyl acetate 27.01
    trichloroethylene 102.03
    n-nonanol 6.64
    cyclohexanol 8.21
    benzyl alcohol 29.16
    2-ethylhexanol 9.63
    isooctanol 6.46
    dipropyl ether 21.81
    1,2-dichlorobenzene 16.66
    ethyl lactate 46.04
    propylene carbonate 92.27
    n-methylformamide 209.15
    2-pentanol 9.54
    n-pentane 0.4
    1-propoxy-2-propanol 45.42
    1-methoxy-2-propyl acetate 62.57
    2-(2-methoxypropoxy) propanol 43.14
    mesitylene 2.59
    ε-caprolactone 54.29
    p-cymene 4.96
    epichlorohydrin 187.87
    1,1,1-trichloroethane 34.15
    2-aminoethanol 60.12
    morpholine-4-carbaldehyde 138.76
    sulfolane 158.11
    2,2,4-trimethylpentane 0.63
    2-methyltetrahydrofuran 52.86
    n-hexyl acetate 14.26
    isooctane 0.39
    2-(2-butoxyethoxy)ethanol 59.22
    sec-butyl acetate 28.21
    tert-butyl acetate 38.74
    decalin 0.73
    glycerin 96.38
    diglyme 134.04
    acrylic acid 89.27
    isopropyl myristate 8.56
    n-butyric acid 86.01
    acetyl acetate 99.46
    di(2-ethylhexyl) phthalate 12.45
    ethyl propionate 58.03
    nitromethane 545.95
    1,2-diethoxyethane 55.62
    benzonitrile 32.65
    trioctyl phosphate 7.12
    1-bromopropane 9.95
    gamma-valerolactone 184.57
    n-decanol 5.53
    triethyl phosphate 24.29
    4-methyl-2-pentanol 7.82
    propionitrile 75.54
    vinylene carbonate 97.43
    1,1,2-trichlorotrifluoroethane 157.92
    DMS 37.1
    cumene 3.85
    2-octanol 4.19
    2-hexanone 35.51
    octyl acetate 10.52
    limonene 5.56
    1,2-dimethoxyethane 245.37
    ethyl orthosilicate 22.6
    tributyl phosphate 10.97
    diacetone alcohol 49.25
    N,N-dimethylaniline 18.64
    acrylonitrile 118.83
    aniline 20.32
    1,3-propanediol 60.56
    bromobenzene 9.77
    dibromomethane 19.2
    1,1,2,2-tetrachloroethane 88.28
    2-methyl-cyclohexyl acetate 22.34
    tetrabutyl urea 12.85
    diisobutyl methanol 7.8
    2-phenylethanol 23.04
    styrene 6.65
    dioctyl adipate 16.84
    dimethyl sulfate 135.71
    ethyl butyrate 39.43
    methyl lactate 80.99
    butyl lactate 18.63
    diethyl carbonate 37.85
    propanediol butyl ether 26.15
    triethyl orthoformate 33.14
    p-tert-butyltoluene 4.9
    methyl 4-tert-butylbenzoate 25.4
    morpholine 131.34
    tert-butylamine 11.81
    n-dodecanol 4.61
    dimethoxymethane 204.29
    ethylene carbonate 81.75
    cyrene 41.02
    2-ethoxyethyl acetate 34.76
    2-ethylhexyl acetate 19.54
    1,2,4-trichlorobenzene 22.79
    4-methylpyridine 37.92
    dibutyl ether 11.76
    2,6-dimethyl-4-heptanol 7.8
    DEF 74.35
    dimethyl isosorbide 71.25
    tetrachloroethylene 47.86
    eugenol 30.38
    triacetin 34.66
    span 80 26.35
    1,4-butanediol 36.11
    1,1-dichloroethane 26.87
    2-methyl-1-pentanol 15.74
    methyl formate 199.59
    2-methyl-1-butanol 12.42
    n-decane 0.65
    butyronitrile 46.28
    3,7-dimethyl-1-octanol 7.18
    1-chlorooctane 2.83
    1-chlorotetradecane 1.67
    n-nonane 0.51
    undecane 0.53
    tert-butylcyclohexane 0.77
    cyclooctane 0.28
    cyclopentanol 14.25
    tetrahydropyran 43.89
    tert-amyl methyl ether 21.41
    2,5,8-trioxanonane 91.74
    1-hexene 2.99
    2-isopropoxyethanol 63.95
    2,2,2-trifluoroethanol 84.21
    methyl butyrate 71.47

    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