2,2'-Methylenebis(4-aminophenol) dihydrochloride

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  • Identifiers

    CAS number
    27311-52-0

    Molecular formula
    C13H16Cl2N2O2

    SMILES
    C1=CC(=C(C=C1N)CC2=C(C=CC(=C2)N)O)O.Cl.Cl

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Phenolic 49.45%
    Burnt 36.17%
    Meaty 32.96%
    Smoky 32.15%
    Odorless 30.34%
    Fruity 28.68%
    Sweet 27.57%
    Animal 27.44%
    Savory 24.78%
    Medicinal 23.59%

     

    Flavor
    Bitter 50.43%
    Fruity 36.96%
    Mild 36.52%
    Phenolic 35.81%
    Sweet 32.74%
    Meaty 24.48%
    Medicinal 22.33%
    Smoked 20.96%
    Orange flower 20.89%
    Very strong 20.71%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    7.56 (neutral)

    Molecular weight
    303.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    508°C

    Flash point

    • 267.63 ˚C est.

  • Synonyms

    • 27311-52-0
    • 2,2'-Methylenebis(4-aminophenol) dihydrochloride
    • UNII-NOJ4K5V5UH
    • NOJ4K5V5UH
    • 2,2'-Methylenebis-4-aminophenol HCl
    • Phenol, 2,2'-methylenebis(4-amino, dihydrochloride
    • 2,2'-Methylenebis-4-aminophenol HCl [INCI]
    • DTXSID10181758
    • 2,2'-Methylenebis[4-aminophenol] dihydrochloride
    • RefChem:80748
    • DTXCID50104249
    • Bis-(5-Amino-2-Hydroxyphenyl)Methane Dihydrochloride
    • bis(5-amino-2-hydroxyphenyl)methan dihydrochloride
    • MFCD07368625
    • Bis-(5-amino-2-hydroxyphenyl)methane 2HCl
    • C13H16Cl2N2O2
    • 4-amino-2-[(5-amino-2-hydroxyphenyl)methyl]phenol;dihydrochloride
    • Bis(5-amino-2-hydroxyphenyl)methan diHCl
    • 2,2'-Methylenebis(4-aminophenol)dihydrochloride
    • 2,2'-Methylenebis[4-aminophenol]dihydrochloride
    • Bis-(5-Amino-2-Hydroxyphenyl)methane hydrochloride
    • SCHEMBL1426099
    • SCHEMBL30892405
    • WKERZZAEPVPFPO-UHFFFAOYSA-N
    • AKOS015889768
    • AS-13569
    • SY284387
    • DB-022672
    • CS-0199070
    • 2,2'-Methylenbis(4-aminophenol)dihydrochlorid
    • 2,2'-METHYLENEBIS(4-AMINOPHENOL) 2HCL
    • 311M520
    • BIS-(5-AMINO-2-HYDROXYPHENYL)METHANE 2HCI
    • F219234
    • Q27284978
    • 2,2'-Methylenebis(4-aminophenol)--hydrogen chloride (1/2)
    • 4-amino-2-[(5-amino-2-hydroxy-phenyl)methyl]phenol;dihydrochloride
    • 4-amino-2-[(5-amino-2-hydroxyphenyl)methyl]phenol,dihydrochloride
    • 2,2 inverted exclamation mark -Methylenebis(4-aminophenol) Dihydrochloride
    • 27311-52-0

  • Applications

    Chemical name: 2,2'-Methylenebis(4-aminophenol) dihydrochloride; CAS number: 27311-52-0. It is primarily used as a curing agent for epoxy resins, enabling crosslinking to improve coatings, adhesives, and composite materials in electronics and industrial applications; it also serves as a crosslinking component in polymer formulations such as polyurethanes and polyureas; it functions as an intermediate in the synthesis of specialty polymers and may serve as a starting material for dye or pigment chemistries; the dihydrochloride salt form enhances water solubility and handling for aqueous epoxy systems.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.91
    methanol 17.94
    isopropanol 2.14
    water 2.26
    ethyl acetate 3.85
    n-propanol 3.12
    acetone 4.04
    n-butanol 1.87
    acetonitrile 3.76
    DMF 42.88
    toluene 0.2
    isobutanol 1.06
    1,4-dioxane 4.94
    methyl acetate 5.16
    THF 37.14
    2-butanone 3.91
    n-pentanol 1.15
    sec-butanol 1.37
    n-hexane 0.03
    ethylene glycol 9.4
    NMP 27.49
    cyclohexane 0.03
    DMSO 84.95
    n-butyl acetate 2.05
    n-octanol 0.5
    chloroform 0.31
    n-propyl acetate 1.71
    acetic acid 33.21
    dichloromethane 0.15
    cyclohexanone 3.79
    propylene glycol 7.3
    isopropyl acetate 2.09
    DMAc 95.89
    2-ethoxyethanol 23.04
    isopentanol 1.4
    n-heptane 0.09
    ethyl formate 7.22
    1,2-dichloroethane 0.27
    n-hexanol 1.82
    2-methoxyethanol 51.46
    isobutyl acetate 0.63
    tetrachloromethane 0.37
    n-pentyl acetate 1.05
    transcutol 16.01
    n-heptanol 1.37
    ethylbenzene 0.16
    MIBK 1.55
    2-propoxyethanol 17.36
    tert-butanol 4.12
    MTBE 1.44
    2-butoxyethanol 8.54
    propionic acid 7.9
    o-xylene 0.31
    formic acid 70.22
    diethyl ether 1.09
    m-xylene 0.23
    p-xylene 0.21
    chlorobenzene 0.22
    dimethyl carbonate 10.16
    n-octane 0.04
    formamide 128.9
    cyclopentanone 18.82
    2-pentanone 2.46
    anisole 1.52
    cyclopentyl methyl ether 2.77
    gamma-butyrolactone 33.62
    1-methoxy-2-propanol 19.87
    pyridine 3.53
    3-pentanone 2.06
    furfural 30.36
    n-dodecane 0.02
    diethylene glycol 27.72
    diisopropyl ether 0.31
    tert-amyl alcohol 2.57
    acetylacetone 7.31
    n-hexadecane 0.02
    acetophenone 2.71
    methyl propionate 6.12
    isopentyl acetate 1.89
    trichloroethylene 0.86
    n-nonanol 0.64
    cyclohexanol 0.92
    benzyl alcohol 2.13
    2-ethylhexanol 0.96
    isooctanol 1.04
    dipropyl ether 1.68
    1,2-dichlorobenzene 0.42
    ethyl lactate 5.52
    propylene carbonate 11.49
    n-methylformamide 38.23
    2-pentanol 0.83
    n-pentane 0.03
    1-propoxy-2-propanol 8.53
    1-methoxy-2-propyl acetate 7.08
    2-(2-methoxypropoxy) propanol 7.62
    mesitylene 0.2
    ε-caprolactone 5.73
    p-cymene 0.37
    epichlorohydrin 11.85
    1,1,1-trichloroethane 0.42
    2-aminoethanol 13.74
    morpholine-4-carbaldehyde 30.36
    sulfolane 43.23
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 5.43
    n-hexyl acetate 1.09
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 9.53
    sec-butyl acetate 0.96
    tert-butyl acetate 3.52
    decalin 0.03
    glycerin 31.45
    diglyme 20.5
    acrylic acid 12.27
    isopropyl myristate 0.6
    n-butyric acid 10.41
    acetyl acetate 3.98
    di(2-ethylhexyl) phthalate 1.48
    ethyl propionate 2.43
    nitromethane 80.19
    1,2-diethoxyethane 2.27
    benzonitrile 1.1
    trioctyl phosphate 1.06
    1-bromopropane 0.1
    gamma-valerolactone 34.16
    n-decanol 0.51
    triethyl phosphate 2.87
    4-methyl-2-pentanol 0.73
    propionitrile 1.96
    vinylene carbonate 8.41
    1,1,2-trichlorotrifluoroethane 28.25
    DMS 2.58
    cumene 0.17
    2-octanol 0.52
    2-hexanone 1.24
    octyl acetate 0.87
    limonene 0.43
    1,2-dimethoxyethane 24.03
    ethyl orthosilicate 2.62
    tributyl phosphate 1.18
    diacetone alcohol 9.71
    N,N-dimethylaniline 1.39
    acrylonitrile 4.33
    aniline 1.48
    1,3-propanediol 16.68
    bromobenzene 0.12
    dibromomethane 0.09
    1,1,2,2-tetrachloroethane 1.04
    2-methyl-cyclohexyl acetate 2.05
    tetrabutyl urea 1.91
    diisobutyl methanol 0.85
    2-phenylethanol 2.66
    styrene 0.17
    dioctyl adipate 1.31
    dimethyl sulfate 23.47
    ethyl butyrate 2.57
    methyl lactate 15.4
    butyl lactate 3.07
    diethyl carbonate 2.57
    propanediol butyl ether 4.84
    triethyl orthoformate 3.14
    p-tert-butyltoluene 0.42
    methyl 4-tert-butylbenzoate 4.87
    morpholine 9.78
    tert-butylamine 0.94
    n-dodecanol 0.38
    dimethoxymethane 22.06
    ethylene carbonate 6.16
    cyrene 11.76
    2-ethoxyethyl acetate 3.27
    2-ethylhexyl acetate 1.19
    1,2,4-trichlorobenzene 0.74
    4-methylpyridine 1.77
    dibutyl ether 0.47
    2,6-dimethyl-4-heptanol 0.85
    DEF 6.38
    dimethyl isosorbide 16.1
    tetrachloroethylene 1.24
    eugenol 6.11
    triacetin 3.41
    span 80 4.81
    1,4-butanediol 4.89
    1,1-dichloroethane 0.14
    2-methyl-1-pentanol 1.05
    methyl formate 25.27
    2-methyl-1-butanol 1.23
    n-decane 0.04
    butyronitrile 1.51
    3,7-dimethyl-1-octanol 0.62
    1-chlorooctane 0.12
    1-chlorotetradecane 0.07
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.03
    cyclooctane 0.02
    cyclopentanol 2.21
    tetrahydropyran 1.8
    tert-amyl methyl ether 1.37
    2,5,8-trioxanonane 15.85
    1-hexene 0.1
    2-isopropoxyethanol 7.26
    2,2,2-trifluoroethanol 21.3
    methyl butyrate 3.23

    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