4,4'-Methylenedianiline

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  • Identifiers

    CAS number
    101-77-9

    Molecular formula
    C13H14N2

    SMILES
    C1=CC(=CC=C1CC2=CC=C(C=C2)N)N

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 67.3%
    Sweet 54.69%
    Animal 43.98%
    Grape 32.18%
    Honey 29.94%
    Rose 29.73%
    Phenolic 29.13%
    Orange 28.19%
    Neroli 26.92%
    Woody 26.07%

     

    Flavor
    Sweet 36.15%
    Floral 32.69%
    Phenolic 32.43%
    Plastic 27.67%
    Medicinal 24.71%
    Fruity 23.6%
    Rose 23.07%
    Mild 22.82%
    Penetrating 22.58%
    Sulfurous 22.23%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    4.87 (weak acid)

    Molecular weight
    198.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 197 to 198 °F (NTP, 1992)
    • 92.5 °C
    • 91.5-92 °C
    • 198 °F

    Boiling point

    • 748 to 750 °F at 768 mmHg (NTP, 1992)
    • 398 °C
    • BP: 257 °C at 18 mm Hg; 249-253 °C at 15 mm Hg; 232 °C at 9 mm Hg
    • at 102kPa: 398-399 °C
    • 748 °F

    Flash point

    • 217.05 ˚C est.
    • 430 °F (NTP, 1992)
    • 220 °C
    • 428 °F (220 °C) (closed cup)
    • 220 °C c.c.
    • 430 °F
    • 374 °F

    Solubility expt.

    • less than 1 mg/mL at 66 °F (NTP, 1992)
    • Slightly sol in cold water. Very sol in alcohol, benzene, ether
    • Solubility (g/100mL solvent at 25 °C): 273.0 in acetone; 9.0 in benzene; 0.7 in carbon tetrachloride; 9.5 in ethyl ether; 143.0 in methanol; 0.1 in water
    • In water, 1.00X10+3 mg/L at 25 °C
    • 1 mg/mL at 25 °C
    • Solubility in water: poor
    • 0.1%

  • Synonyms

    • 4,4'-Methylenedianiline
    • 101-77-9
    • 4,4'-DIAMINODIPHENYLMETHANE
    • Dadpm
    • Methylenedianiline
    • Tonox
    • Dianilinomethane
    • 4-[(4-aminophenyl)methyl]aniline
    • Bis(4-aminophenyl)methane
    • p,p'-Methylenedianiline
    • Dianilinemethane
    • Benzenamine, 4,4'-methylenebis-
    • 4,4-Methylenedianiline
    • p,p'-Diaminodiphenylmethane
    • Epicure DDM
    • Epikure DDM
    • Bis(p-aminophenyl)methane
    • Curithane
    • 4-(4-Aminobenzyl)aniline
    • Jeffamine AP-20
    • Sumicure M
    • Diaminodiphenylmethane
    • 4,4'-Diphenylmethanediamine
    • Ancamine TL
    • Di-(4-aminophenyl)methane
    • 4,4'-Methylenebis(benzeneamine)
    • Methylenebis(aniline)
    • Bis-p-aminofenylmethan
    • 4,4'-Methylene dianiline
    • Araldite hardener 972
    • Di(4-aminophenyl)methane
    • p,p'-Diaminodifenylmethan
    • 4,4'-Methylenebisaniline
    • 4,4'-Diaminodiphenylmethan
    • 4,4'-Methylenebisbenzenamine
    • Aniline, 4,4'-methylenedi-
    • 4,4'-Dimethylenediamine
    • Methylenedianiline (VAN)
    • Avaldite HT 972
    • 4,4'-Methylenebis(aniline)
    • HT 972
    • NCI-C54604
    • NSC 4709
    • Methylenebis[aniline]
    • Bis(aminophenyl)methane
    • CCRIS 1010
    • Bis-p-aminofenylmethan [Czech]
    • bis-p-aminophenylmethane
    • GG5LL7OBZC
    • CHEBI:32506
    • HSDB 2541
    • alpha-(p-aminophenyl)-p-toluidine
    • di-(p-aminophenyl)methane
    • p,p'-Diaminodifenylmethan [Czech]
    • 4,4'-methylene-dianiline
    • EINECS 202-974-4
    • 4,4'-Methylenedibenzenamine
    • 4,4'-Diaminodiphenylmethan [German]
    • p-Toluidine, alpha-(p-aminophenyl)-
    • UN2651
    • 4,4'-Methylene(bisaniline)
    • 4,4'-Methylenebis[aniline]
    • 4,4'-Diaminobiphenyl methane
    • BRN 0474706
    • DTXSID6022422
    • AI3-02615
    • 4,4-DIAMINODIPHENYLMETHANE
    • NSC-4709
    • 4,4'-Diaminodiphenylmethane (MDA)
    • p, p'-Methylenedianiline
    • METHYLENEDIANILINE-
    • 1219795-26-2
    • 4,4'-methanediyldianiline
    • 4,4'-Methylenedi-Aniline
    • 4,4?-Diaminodiphenylmethane
    • 4, 4'-Diphenylmethanediamine
    • 4,4'-Diaminodiphenyl methane
    • 4-(4-Aminobenzyl)phenylamine
    • 4, 4'-Methylenebis(aniline)
    • 4,4'-Methylenedianiline--d8
    • 4,4'-Methylenebis-Benzenamine
    • NSC4709
    • EC 202-974-4
    • 4,4-DIPHENYLMETHANE DIAMINE
    • 4,4'-DIPHENYLMETHANE DIAMINE
    • MFCD00007914
    • p-Toluidine, .alpha.-(p-aminophenyl)-
    • 4,4'-METHYLENEDIANILINE [HSDB]
    • 4,4'-METHYLENEDIANILINE [IARC]
    • P,P'-DIAMINODIPHENYLMETHANE [MI]
    • DTXCID402422
    • 4-((4-aminophenyl)methyl)aniline
    • BIS-(4-AMINOPHENYL)METHANE
    • BIS-P-AMINOFENYLMETHAN (CZECH)
    • 4,4'-METHYLENEDIANILINE (IARC)
    • CAS-101-77-9
    • P,P'-DIAMINODIFENYLMETHAN (CZECH)
    • 4,4'-DIAMINODIPHENYLMETHAN (GERMAN)
    • UNII-GG5LL7OBZC
    • para'-Diaminodiphenyl-methane
    • Bispaminofenylmethan
    • Jeffamine AP20
    • 4,4'-MDA
    • p,p'Methylenedianiline
    • 4(4Aminobenzyl)aniline
    • 4,4'Dimethylenediamine
    • Di(4aminophenyl)methane
    • Bis(paminophenyl)methane
    • p,p'Diaminodifenylmethan
    • A1IHK
    • 4,4'Methylenebisaniline
    • Bis(4aminophenyl)methane
    • Aniline,4'-methylenedi-
    • p,p'diaminodiphenylmethane
    • 4,4'diaminodiphenylmethan
    • 4,4'diaminodiphenylmethane
    • 4,4'Diphenylmethanediamine
    • ACMEX H 84BM
    • Aniline, 4,4'methylenedi
    • ARALDITE HT 972
    • Epitope ID:116050
    • ARALDITE R 972
    • Di(para-aminophenyl)methane
    • WLN: ZR D1R DZ
    • 4,4'-DIAMINODITAN
    • ANCAMINE 1692
    • methylenebis(4-aminobenzene)
    • Oprea1_406523

  • Applications

    4,4'-Methylenedianiline (CAS 101-77-9) is primarily used as an essential intermediate in the production of methylene diphenyl diisocyanate (MDI) via phosgenation, a key diisocyanate for polyurethane raw materials. It serves as a building block in polyurethane resins and formulations, including rigid and flexible foams, coatings, sealants, and elastomer systems. It is also employed in the synthesis of polyurethane prepolymers and adhesive systems, where it contributes to chain extension and crosslinking. Additionally, the diamine can be used as a curing agent for epoxy resins in certain high-performance formulations, and may be evaluated for specialty polymers and high-temperature coatings, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 68.06
    methanol 213.36
    isopropanol 26.97
    water 3.79
    ethyl acetate 206.61
    n-propanol 54.92
    acetone 365.72
    n-butanol 32.72
    acetonitrile 239.39
    DMF 699.6
    toluene 11.06
    isobutanol 18.98
    1,4-dioxane 182.97
    methyl acetate 236.4
    THF 482.94
    2-butanone 215.69
    n-pentanol 22.98
    sec-butanol 17.93
    n-hexane 0.83
    ethylene glycol 52.26
    NMP 168.41
    cyclohexane 0.69
    DMSO 681.1
    n-butyl acetate 63.81
    n-octanol 6.43
    chloroform 98.97
    n-propyl acetate 75.67
    acetic acid 172.73
    dichloromethane 41.63
    cyclohexanone 102.83
    propylene glycol 50.48
    isopropyl acetate 69.03
    DMAc 610.31
    2-ethoxyethanol 155.27
    isopentanol 20.03
    n-heptane 1.6
    ethyl formate 163.06
    1,2-dichloroethane 56.01
    n-hexanol 28.04
    2-methoxyethanol 305.85
    isobutyl acetate 32.04
    tetrachloromethane 14.36
    n-pentyl acetate 19.01
    transcutol 169.65
    n-heptanol 13.38
    ethylbenzene 5.76
    MIBK 40.12
    2-propoxyethanol 140.39
    tert-butanol 35.5
    MTBE 42.66
    2-butoxyethanol 54.54
    propionic acid 109.67
    o-xylene 7.62
    formic acid 158.85
    diethyl ether 56.9
    m-xylene 7.99
    p-xylene 8.53
    chlorobenzene 25.59
    dimethyl carbonate 208.81
    n-octane 0.6
    formamide 408.78
    cyclopentanone 360.61
    2-pentanone 121.81
    anisole 54.77
    cyclopentyl methyl ether 62.41
    gamma-butyrolactone 438.98
    1-methoxy-2-propanol 163.94
    pyridine 126.27
    3-pentanone 113.22
    furfural 298.3
    n-dodecane 0.42
    diethylene glycol 140.14
    diisopropyl ether 8.59
    tert-amyl alcohol 21.93
    acetylacetone 232.35
    n-hexadecane 0.46
    acetophenone 54.29
    methyl propionate 218.3
    isopentyl acetate 38.0
    trichloroethylene 156.25
    n-nonanol 7.37
    cyclohexanol 11.28
    benzyl alcohol 33.99
    2-ethylhexanol 13.14
    isooctanol 9.42
    dipropyl ether 38.98
    1,2-dichlorobenzene 28.88
    ethyl lactate 54.37
    propylene carbonate 150.06
    n-methylformamide 502.07
    2-pentanol 13.84
    n-pentane 0.64
    1-propoxy-2-propanol 75.72
    1-methoxy-2-propyl acetate 109.67
    2-(2-methoxypropoxy) propanol 40.54
    mesitylene 4.8
    ε-caprolactone 82.42
    p-cymene 6.62
    epichlorohydrin 299.82
    1,1,1-trichloroethane 58.18
    2-aminoethanol 85.17
    morpholine-4-carbaldehyde 223.48
    sulfolane 323.55
    2,2,4-trimethylpentane 0.73
    2-methyltetrahydrofuran 91.52
    n-hexyl acetate 17.39
    isooctane 0.55
    2-(2-butoxyethoxy)ethanol 61.63
    sec-butyl acetate 33.44
    tert-butyl acetate 63.63
    decalin 0.76
    glycerin 117.92
    diglyme 176.43
    acrylic acid 124.55
    isopropyl myristate 8.64
    n-butyric acid 126.19
    acetyl acetate 121.53
    di(2-ethylhexyl) phthalate 12.92
    ethyl propionate 84.6
    nitromethane 869.49
    1,2-diethoxyethane 59.7
    benzonitrile 41.13
    trioctyl phosphate 8.92
    1-bromopropane 13.02
    gamma-valerolactone 358.29
    n-decanol 5.92
    triethyl phosphate 27.94
    4-methyl-2-pentanol 9.46
    propionitrile 122.31
    vinylene carbonate 139.9
    1,1,2-trichlorotrifluoroethane 264.63
    DMS 46.77
    cumene 4.83
    2-octanol 5.32
    2-hexanone 60.75
    octyl acetate 12.43
    limonene 7.73
    1,2-dimethoxyethane 286.37
    ethyl orthosilicate 26.63
    tributyl phosphate 12.36
    diacetone alcohol 73.68
    N,N-dimethylaniline 25.07
    acrylonitrile 223.84
    aniline 38.79
    1,3-propanediol 91.16
    bromobenzene 18.71
    dibromomethane 21.44
    1,1,2,2-tetrachloroethane 123.46
    2-methyl-cyclohexyl acetate 28.37
    tetrabutyl urea 15.37
    diisobutyl methanol 8.32
    2-phenylethanol 34.64
    styrene 8.87
    dioctyl adipate 16.31
    dimethyl sulfate 251.96
    ethyl butyrate 56.42
    methyl lactate 128.29
    butyl lactate 24.06
    diethyl carbonate 46.5
    propanediol butyl ether 28.55
    triethyl orthoformate 43.06
    p-tert-butyltoluene 7.15
    methyl 4-tert-butylbenzoate 35.74
    morpholine 186.73
    tert-butylamine 14.87
    n-dodecanol 4.68
    dimethoxymethane 435.27
    ethylene carbonate 111.6
    cyrene 52.47
    2-ethoxyethyl acetate 50.33
    2-ethylhexyl acetate 28.3
    1,2,4-trichlorobenzene 35.91
    4-methylpyridine 70.81
    dibutyl ether 10.88
    2,6-dimethyl-4-heptanol 8.32
    DEF 138.36
    dimethyl isosorbide 95.91
    tetrachloroethylene 83.5
    eugenol 39.69
    triacetin 39.96
    span 80 29.2
    1,4-butanediol 34.1
    1,1-dichloroethane 44.88
    2-methyl-1-pentanol 14.3
    methyl formate 397.29
    2-methyl-1-butanol 16.94
    n-decane 0.65
    butyronitrile 63.98
    3,7-dimethyl-1-octanol 7.1
    1-chlorooctane 3.4
    1-chlorotetradecane 1.67
    n-nonane 0.55
    undecane 0.5
    tert-butylcyclohexane 0.96
    cyclooctane 0.38
    cyclopentanol 25.3
    tetrahydropyran 75.49
    tert-amyl methyl ether 26.91
    2,5,8-trioxanonane 106.8
    1-hexene 4.28
    2-isopropoxyethanol 66.28
    2,2,2-trifluoroethanol 103.25
    methyl butyrate 101.63

    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