4,4'-Methylenebis(2-chloroaniline)

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  • Identifiers

    CAS number
    101-14-4

    Molecular formula
    C13H12Cl2N2

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

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Animal 34.91%
    Burnt 28.89%
    Phenolic 27.08%
    Floral 26.77%
    Meaty 26.23%
    Sweet 26.16%
    Fruity 25.19%
    Odorless 25.01%
    Grape 21.91%
    Cheesy 21.89%

     

    Flavor
    Bitter 40.43%
    Mild 27.35%
    Very strong 21.18%
    Odorless 21.17%
    Indole 20.75%
    Orange flower 20.24%
    Nitrile 20.05%
    Fruity 19.65%
    Meaty 19.59%
    Scallion 19.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.8

    pKa est.
    4.54 (weak acid)

    Molecular weight
    267.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    447°C

    Melting point expt.

    • 210 to 225 °F (NTP, 1992)
    • 110 °C
    • 210-225 °F
    • 230 °F

    Flash point

    • 218.67 ˚C est.
    • 113 °C c.c.

    Solubility expt.

    • less than 1 mg/mL at 77 °F (NTP, 1992)
    • Soluble in hot methyl ethyl ketone, acetone, esters, and aromatic hydrocarbons
    • Sol in dimethyl sulfoxide, dimethyl formamide
    • Solubl in dilulte acids, ether, alcohol
    • Soluble in carbon tetrachloride
    • Slightly soluble in water; sol in oxygenated solvents
    • Solubility in water: none
    • Slight

  • Synonyms

    • 101-14-4
    • 4,4'-METHYLENEBIS(2-CHLOROANILINE)
    • Bisamine
    • MOCA
    • Cyanaset
    • Quodorole
    • 4,4'-Methylene bis(2-chloroaniline)
    • Methylenebis(chloroaniline)
    • Dacpm
    • Curalin M
    • Diamet Kh
    • MBOCA
    • CL-Mda
    • Bis amine
    • Millionate M
    • Bisamine S
    • Cuamine M
    • Cuamine MT
    • Curene 442
    • MOCA (curing agent)
    • Bis-amine A
    • 4,4'-Methylene-bis(2-chloroaniline)
    • Rcra waste number U158
    • Benzenamine, 4,4'-methylenebis[2-chloro-
    • Bis(3-chloro-4-aminophenyl)methane
    • Bis(4-amino-3-chlorophenyl)methane
    • 4,4'-Methylenebis(o-chloroaniline)
    • LD 813
    • Methylene-bis-orthochloroaniline
    • 3,3'-Dichloro-4,4'-diaminodiphenylmethane
    • 4,4'-Diamino-3,3'-dichlorodiphenylmethane
    • Methylenebis(3-chloro-4-aminobenzene)
    • 4,4-Metilene-bis-o-cloroanilina
    • 4,4'-Methylene-bis-(2-chloroaniline)
    • Di-(4-amino-3-clorofenil)metano
    • p,p'-Methylenebis(o-chloroaniline)
    • 4,4'-Methylenebis[2-chloroaniline]
    • CCRIS 389
    • 4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline
    • DTXSID5020865
    • 4,4'-Methylenebis(2-chlorobenzenamine)
    • HSDB 2629
    • Di(4-amino-3-chlorophenyl)methane
    • Benzenamine, 4,4'-methylenebis(2-chloro-
    • 4,4'-Methylene(bis)-chloroaniline
    • Di(-4-amino-3-chlorophenyl)methane
    • EINECS 202-918-9
    • 3L2W5VTT2A
    • NSC 52954
    • Methylene 4,4'-bis(o-chloroaniline)
    • 4,4'-Methylenebis-2-chlorobenzenamine
    • p,p'-Methylenebis(alpha-chloroaniline)
    • p,p'-Methylenebis(ortho-chloroaniline)
    • Aniline, 4,4'-methylenebis(2-chloro-
    • BRN 1882318
    • 2,2'-Dichloro-4,4'-methylenedianiline
    • 3,3'-Dicloro-4,4'-diaminodifenilmetano
    • CHEBI:28124
    • 3,3'-Dichlor-4,4'-diaminodiphenylmethan
    • 3,3'-Dichloro-4,4'-diaminodifenilmetano
    • 4,4-Metilene-bis-o-cloroanilina [Italian]
    • Di-(4-amino-3-clorofenil)metano [Italian]
    • 4,4'-Diamino-3,3'-dichlorodiphenyl methane
    • 4,4'-Methylenebis[o-chloroaniline]
    • NSC-52954
    • Methylene-4,4'-bis(o-chloroaniline)
    • 4,4'-methanediylbis(2-chloroaniline)
    • 3,3'-Dichlor-4,4'-diaminodiphenylmethan [German]
    • 3,3'-Dichloro-4,4'-diaminodifenilmetano [Italian]
    • 3,3'-Dicloro-4,4'-diaminodifenilmetano [Italian]
    • Aniline, 4,4'-methylenebis[2-chloro-
    • methylenebis(o-chloroaniline)
    • DTXCID50865
    • EC 202-918-9
    • p,p'-Methylenebis[o-chloroaniline]
    • 1-13-00-00074 (Beilstein Handbook Reference)
    • 4,4'-Methylenebis[2-chloroaniline
    • NSC52954
    • 4,4'-Methylene-bis-2-chloroaniline
    • 4,4'-methylene bis(o-chloroaniline)
    • Methylenebis[3-Chloro-4-aminobenzene]
    • 2,2'-dichloro-4,4'-methylendianiline
    • 4,4'-Methylenebis[2-chlorobenzenamine]
    • p,p'-Methylenebis[.alpha.-chloroaniline]
    • METHYLENEBIS(CHLOROANILINE) [HSDB]
    • DI-(4-AMINO-3-CHLOROPHENYL)METHANE
    • 4,4'-METHYLENEBIS(2-CHLOROANILINE) [MI]
    • 4,4'-METHYLENEBIS(2-CHLOROANILINE) [IARC]
    • 4-[(4-amino-3-chloro-phenyl)methyl]-2-chloro-aniline
    • 4,4'-Methylenebis(2-chloroaniline
    • 4, (4'-Methylenebis(o-chloroaniline))
    • 4, {4'-Methylenebis[o-chloroaniline]}
    • 27342-75-2
    • p,p'-Methylenebis(.alpha.-chloroaniline)
    • C13H12Cl2N2
    • 4,4'-Methylenebis(2-chloroaniline) (~90%)
    • 4,4-METILENE-BIS-O-CLOROANILINA (ITALIAN)
    • 3,3'-Dichloro-4,4'-diaminodifenilmetano (Italian)
    • 4,4'-METHYLENEBIS(2-CHLOROANILINE) (IARC)
    • 4-((4-amino-3-chlorophenyl)methyl)-2-chloroaniline
    • DI-(4-AMINO-3-CLOROFENIL)METANO (ITALIAN)
    • 4,4-Methylene bis(2-chloroaniline)
    • RCRA waste no. U158
    • UNII-3L2W5VTT2A
    • 4-((4-amino-3-chloro-phenyl)methyl)-2-chloro-aniline
    • Methylene Bis(chloroaniline)
    • 3,3'-DICHLOR-4,4'-DIAMINODIPHENYLMETHAN (GERMAN)
    • 3,3'-DICLORO-4,4'-DIAMINODIFENILMETANO (ITALIAN)
    • 4,4'-Methylene-bis(2-chloroaniline), analytical standard
    • Methylenebis(2-chloroaniline)
    • 4,4'-Methylenebis-(2-Chlorobenzenamine)
    • Bisamine A
    • CLMda
    • 4,4'-Methylenebis(o-chloro aniline)
    • DIAMET X
    • 2,2'Dichloro-4,4'-methylene dianiline
    • MOCA; MBOCA
    • Benzenamine, 4,4'-methylenebis(2-chloro)-
    • 3,3'-Dichloro-4,4'-diaminodiphenyl methane
    • CBMicro_013250
    • 3,4'-diaminodifenilmetano
    • 3,4'-diaminodiphenylmethan
    • 4,4Metilenebisocloroanilina
    • Cambridge id 5180272
    • Di(4amino3clorofenil)metano
    • methylenebisorthochloroaniline
    • BENZENAMINE,4,4'-METHYLENEBIS[2-CHLORO-
    • Oprea1_093196

  • Applications

    4,4'-Methylenebis(2-chloroaniline) (CAS 101-14-4) is used as a crosslinking/curing agent in polyurethane systems and as a reactive intermediate in the synthesis of dye precursors and pigments; it is also employed as a crosslinker for epoxy resin coatings and in specialty polymers and adhesives formulations. In the polymer and coatings sectors, it enables network formation in rigid and flexible foams, coatings, and adhesive systems. Handling is subject to strict controls due to toxicity concerns, and use is governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 68.36
    methanol 78.19
    isopropanol 42.28
    water 0.93
    ethyl acetate 226.63
    n-propanol 62.87
    acetone 433.75
    n-butanol 53.07
    acetonitrile 67.88
    DMF 907.13
    toluene 20.48
    isobutanol 28.03
    1,4-dioxane 366.42
    methyl acetate 209.85
    THF 1050.46
    2-butanone 294.55
    n-pentanol 33.0
    sec-butanol 30.5
    n-hexane 0.29
    ethylene glycol 21.1
    NMP 263.44
    cyclohexane 0.46
    DMSO 452.62
    n-butyl acetate 74.15
    n-octanol 7.78
    chloroform 126.99
    n-propyl acetate 78.23
    acetic acid 138.97
    dichloromethane 76.59
    cyclohexanone 200.07
    propylene glycol 36.29
    isopropyl acetate 93.2
    DMAc 882.7
    2-ethoxyethanol 210.93
    isopentanol 29.91
    n-heptane 1.08
    ethyl formate 158.44
    1,2-dichloroethane 64.04
    n-hexanol 27.45
    2-methoxyethanol 380.82
    isobutyl acetate 35.32
    tetrachloromethane 12.06
    n-pentyl acetate 38.62
    transcutol 211.03
    n-heptanol 17.63
    ethylbenzene 5.75
    MIBK 59.59
    2-propoxyethanol 150.53
    tert-butanol 46.48
    MTBE 66.38
    2-butoxyethanol 81.52
    propionic acid 63.87
    o-xylene 9.68
    formic acid 77.7
    diethyl ether 63.54
    m-xylene 11.38
    p-xylene 8.25
    chlorobenzene 35.94
    dimethyl carbonate 172.33
    n-octane 0.47
    formamide 257.24
    cyclopentanone 543.79
    2-pentanone 186.05
    anisole 70.95
    cyclopentyl methyl ether 109.84
    gamma-butyrolactone 570.88
    1-methoxy-2-propanol 227.64
    pyridine 186.37
    3-pentanone 126.2
    furfural 396.51
    n-dodecane 0.35
    diethylene glycol 114.68
    diisopropyl ether 8.88
    tert-amyl alcohol 31.74
    acetylacetone 321.62
    n-hexadecane 0.41
    acetophenone 66.88
    methyl propionate 219.33
    isopentyl acetate 51.22
    trichloroethylene 232.18
    n-nonanol 8.92
    cyclohexanol 22.71
    benzyl alcohol 56.13
    2-ethylhexanol 13.9
    isooctanol 12.93
    dipropyl ether 36.79
    1,2-dichlorobenzene 30.34
    ethyl lactate 49.71
    propylene carbonate 184.35
    n-methylformamide 357.11
    2-pentanol 22.23
    n-pentane 0.43
    1-propoxy-2-propanol 86.95
    1-methoxy-2-propyl acetate 139.08
    2-(2-methoxypropoxy) propanol 46.57
    mesitylene 5.4
    ε-caprolactone 166.6
    p-cymene 6.95
    epichlorohydrin 551.71
    1,1,1-trichloroethane 62.02
    2-aminoethanol 48.06
    morpholine-4-carbaldehyde 399.31
    sulfolane 359.27
    2,2,4-trimethylpentane 0.56
    2-methyltetrahydrofuran 208.8
    n-hexyl acetate 27.46
    isooctane 0.45
    2-(2-butoxyethoxy)ethanol 78.51
    sec-butyl acetate 40.1
    tert-butyl acetate 88.59
    decalin 0.42
    glycerin 73.05
    diglyme 245.43
    acrylic acid 66.83
    isopropyl myristate 10.84
    n-butyric acid 125.7
    acetyl acetate 123.14
    di(2-ethylhexyl) phthalate 13.99
    ethyl propionate 69.35
    nitromethane 592.43
    1,2-diethoxyethane 94.3
    benzonitrile 46.71
    trioctyl phosphate 10.95
    1-bromopropane 18.75
    gamma-valerolactone 739.85
    n-decanol 6.78
    triethyl phosphate 28.29
    4-methyl-2-pentanol 12.11
    propionitrile 50.38
    vinylene carbonate 168.91
    1,1,2-trichlorotrifluoroethane 270.79
    DMS 49.68
    cumene 3.97
    2-octanol 8.6
    2-hexanone 70.43
    octyl acetate 16.01
    limonene 9.33
    1,2-dimethoxyethane 366.73
    ethyl orthosilicate 27.41
    tributyl phosphate 13.66
    diacetone alcohol 106.79
    N,N-dimethylaniline 28.75
    acrylonitrile 89.4
    aniline 63.1
    1,3-propanediol 100.46
    bromobenzene 27.04
    dibromomethane 32.21
    1,1,2,2-tetrachloroethane 154.42
    2-methyl-cyclohexyl acetate 31.08
    tetrabutyl urea 19.1
    diisobutyl methanol 9.37
    2-phenylethanol 44.35
    styrene 9.72
    dioctyl adipate 20.41
    dimethyl sulfate 234.62
    ethyl butyrate 61.87
    methyl lactate 111.74
    butyl lactate 36.61
    diethyl carbonate 42.84
    propanediol butyl ether 42.57
    triethyl orthoformate 50.09
    p-tert-butyltoluene 7.36
    methyl 4-tert-butylbenzoate 43.96
    morpholine 416.3
    tert-butylamine 14.94
    n-dodecanol 5.05
    dimethoxymethane 568.21
    ethylene carbonate 138.28
    cyrene 77.01
    2-ethoxyethyl acetate 97.1
    2-ethylhexyl acetate 33.73
    1,2,4-trichlorobenzene 42.13
    4-methylpyridine 132.64
    dibutyl ether 13.44
    2,6-dimethyl-4-heptanol 9.37
    DEF 213.82
    dimethyl isosorbide 117.95
    tetrachloroethylene 87.13
    eugenol 48.74
    triacetin 49.21
    span 80 36.09
    1,4-butanediol 35.47
    1,1-dichloroethane 57.95
    2-methyl-1-pentanol 20.39
    methyl formate 325.84
    2-methyl-1-butanol 27.49
    n-decane 0.58
    butyronitrile 55.43
    3,7-dimethyl-1-octanol 8.64
    1-chlorooctane 3.77
    1-chlorotetradecane 1.49
    n-nonane 0.46
    undecane 0.44
    tert-butylcyclohexane 0.57
    cyclooctane 0.21
    cyclopentanol 47.75
    tetrahydropyran 161.69
    tert-amyl methyl ether 42.05
    2,5,8-trioxanonane 122.34
    1-hexene 2.68
    2-isopropoxyethanol 94.2
    2,2,2-trifluoroethanol 80.82
    methyl butyrate 103.46

    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