Methylolmethacrylamide

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  • Identifiers

    CAS number
    923-02-4

    Molecular formula
    C5H9NO2

    SMILES
    CC(=C)C(=O)NCO

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 38.77%
    Meaty 35.45%
    Savory 34.08%
    Sulfurous 28.24%
    Roasted 27.55%
    Pungent 26.48%
    Sweet 25.36%
    Cooked 24.16%
    Cheesy 23.73%
    Burnt 21.4%

     

    Flavor
    Odorless 37.55%
    Nutty 28.2%
    Cooked 24.46%
    Roasted 23.03%
    Very mild 22.37%
    Bread crust 20.72%
    Matches 20.72%
    Taco 20.69%
    Musty 20.52%
    Roasted peanuts 20.44%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    8.66 (weak base)

    Molecular weight
    115.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    349°C

    Flash point

    • 133.7 ˚C est.

  • Synonyms

    • N-methylolmethacrylamide
    • 923-02-4
    • Methylolmethacrylamide
    • 2-Propenamide, N-(hydroxymethyl)-2-methyl-
    • Acrylamide, N-(hydroxymethyl)-2-methyl-
    • N-(Hydroxymethyl)-2-methyl-2-propenamide
    • 8BO2025ITR
    • NSC-2691
    • DTXSID2027335
    • MEAA cpd
    • RefChem:163874
    • DTXCID207335
    • 213-086-1
    • N-METHYLOL METHACRYLAMIDE
    • N-(hydroxymethyl)-2-methylprop-2-enamide
    • N-(Hydroxymethyl)methacrylamide
    • N-(hydroxymethyl)-2-methylacrylamide
    • N-hydroxymethyl methacrylamide
    • MFCD00021960
    • EINECS 213-086-1
    • NSC 2691
    • N-hydroxymethylmethacrylamide
    • BRN 0506510
    • UNII-8BO2025ITR
    • N-(Hydroxymethyl)methacrylamid
    • N-(hydroxymethyl)-2-methyl-prop-2-enamide
    • EC 213-086-1
    • SCHEMBL27050
    • SCHEMBL2316848
    • SCHEMBL6047859
    • NSC2691
    • (HYDROXYMETHYL)METHACRYLAMIDE
    • AKOS003238453
    • DB-230974
    • H1774
    • NS00007081
    • ST45025506
    • Q27270148
    • N-(Hydroxymethyl)methacrylamide Solution in Water (stabilized with MEHQ)
    • 923-02-4

  • Applications

    Methylolmethacrylamide (CAS 923-02-4) is typically used as a reactive crosslinking monomer in aqueous acrylic/methacrylic resins, improving water and chemical resistance, hardness, and adhesion in coatings and inks. It serves as a crosslinking agent in adhesives and binders for wood products, packaging, and labels to boost bond strength and heat resistance. In polymer and plastic systems, it is incorporated into thermally or UV-curable resins to tailor crosslink density and performance. In paper finishing and textile finishing, it functions as a crosslinking component to enhance dimensional stability and durability.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 177.85
    methanol 303.14
    isopropanol 126.11
    water 180.95
    ethyl acetate 18.13
    n-propanol 123.17
    acetone 55.84
    n-butanol 93.41
    acetonitrile 37.29
    DMF 243.74
    toluene 3.91
    isobutanol 93.5
    1,4-dioxane 70.2
    methyl acetate 28.45
    THF 105.76
    2-butanone 44.12
    n-pentanol 67.29
    sec-butanol 101.44
    n-hexane 2.19
    ethylene glycol 150.86
    NMP 159.4
    cyclohexane 1.0
    DMSO 183.48
    n-butyl acetate 15.49
    n-octanol 24.76
    chloroform 15.53
    n-propyl acetate 15.31
    acetic acid 112.25
    dichloromethane 17.8
    cyclohexanone 47.95
    propylene glycol 143.49
    isopropyl acetate 14.23
    DMAc 196.33
    2-ethoxyethanol 127.74
    isopentanol 73.87
    n-heptane 1.8
    ethyl formate 40.91
    1,2-dichloroethane 13.49
    n-hexanol 50.05
    2-methoxyethanol 203.84
    isobutyl acetate 12.49
    tetrachloromethane 6.37
    n-pentyl acetate 14.58
    transcutol 95.11
    n-heptanol 28.35
    ethylbenzene 4.46
    MIBK 27.7
    2-propoxyethanol 98.26
    tert-butanol 140.18
    MTBE 47.26
    2-butoxyethanol 58.86
    propionic acid 66.71
    o-xylene 7.12
    formic acid 174.14
    diethyl ether 20.54
    m-xylene 6.87
    p-xylene 6.88
    chlorobenzene 6.74
    dimethyl carbonate 13.25
    n-octane 1.02
    formamide 107.59
    cyclopentanone 73.61
    2-pentanone 32.04
    anisole 18.15
    cyclopentyl methyl ether 31.86
    gamma-butyrolactone 80.33
    1-methoxy-2-propanol 121.22
    pyridine 20.91
    3-pentanone 19.93
    furfural 76.86
    n-dodecane 0.96
    diethylene glycol 109.89
    diisopropyl ether 6.91
    tert-amyl alcohol 113.89
    acetylacetone 30.66
    n-hexadecane 1.01
    acetophenone 22.25
    methyl propionate 23.51
    isopentyl acetate 18.87
    trichloroethylene 23.27
    n-nonanol 20.63
    cyclohexanol 41.08
    benzyl alcohol 32.01
    2-ethylhexanol 23.34
    isooctanol 23.82
    dipropyl ether 11.08
    1,2-dichlorobenzene 8.8
    ethyl lactate 23.31
    propylene carbonate 40.35
    n-methylformamide 116.78
    2-pentanol 49.41
    n-pentane 2.14
    1-propoxy-2-propanol 51.97
    1-methoxy-2-propyl acetate 23.08
    2-(2-methoxypropoxy) propanol 47.55
    mesitylene 5.53
    ε-caprolactone 41.77
    p-cymene 5.92
    epichlorohydrin 61.49
    1,1,1-trichloroethane 11.89
    2-aminoethanol 190.22
    morpholine-4-carbaldehyde 120.77
    sulfolane 117.22
    2,2,4-trimethylpentane 2.59
    2-methyltetrahydrofuran 64.36
    n-hexyl acetate 22.16
    isooctane 1.91
    2-(2-butoxyethoxy)ethanol 56.9
    sec-butyl acetate 11.08
    tert-butyl acetate 22.48
    decalin 1.53
    glycerin 188.17
    diglyme 81.98
    acrylic acid 65.2
    isopropyl myristate 9.6
    n-butyric acid 63.11
    acetyl acetate 11.34
    di(2-ethylhexyl) phthalate 17.07
    ethyl propionate 13.81
    nitromethane 89.82
    1,2-diethoxyethane 19.07
    benzonitrile 19.53
    trioctyl phosphate 13.74
    1-bromopropane 9.14
    gamma-valerolactone 92.26
    n-decanol 15.17
    triethyl phosphate 11.81
    4-methyl-2-pentanol 29.33
    propionitrile 29.05
    vinylene carbonate 34.65
    1,1,2-trichlorotrifluoroethane 73.14
    DMS 14.2
    cumene 5.96
    2-octanol 17.61
    2-hexanone 25.57
    octyl acetate 14.07
    limonene 9.0
    1,2-dimethoxyethane 109.8
    ethyl orthosilicate 11.43
    tributyl phosphate 13.0
    diacetone alcohol 59.28
    N,N-dimethylaniline 19.62
    acrylonitrile 36.06
    aniline 18.24
    1,3-propanediol 160.79
    bromobenzene 4.44
    dibromomethane 11.19
    1,1,2,2-tetrachloroethane 23.52
    2-methyl-cyclohexyl acetate 17.4
    tetrabutyl urea 19.97
    diisobutyl methanol 13.37
    2-phenylethanol 26.02
    styrene 4.48
    dioctyl adipate 15.02
    dimethyl sulfate 33.67
    ethyl butyrate 13.09
    methyl lactate 39.03
    butyl lactate 22.67
    diethyl carbonate 9.32
    propanediol butyl ether 58.92
    triethyl orthoformate 11.73
    p-tert-butyltoluene 6.18
    methyl 4-tert-butylbenzoate 31.14
    morpholine 93.75
    tert-butylamine 60.34
    n-dodecanol 11.03
    dimethoxymethane 68.65
    ethylene carbonate 25.7
    cyrene 60.78
    2-ethoxyethyl acetate 18.67
    2-ethylhexyl acetate 13.29
    1,2,4-trichlorobenzene 11.8
    4-methylpyridine 26.41
    dibutyl ether 9.71
    2,6-dimethyl-4-heptanol 13.37
    DEF 53.8
    dimethyl isosorbide 56.5
    tetrachloroethylene 17.6
    eugenol 37.1
    triacetin 20.24
    span 80 39.06
    1,4-butanediol 97.43
    1,1-dichloroethane 12.72
    2-methyl-1-pentanol 59.3
    methyl formate 77.75
    2-methyl-1-butanol 77.05
    n-decane 1.42
    butyronitrile 34.42
    3,7-dimethyl-1-octanol 22.12
    1-chlorooctane 6.22
    1-chlorotetradecane 2.68
    n-nonane 1.32
    undecane 1.13
    tert-butylcyclohexane 2.32
    cyclooctane 0.7
    cyclopentanol 69.51
    tetrahydropyran 35.35
    tert-amyl methyl ether 36.97
    2,5,8-trioxanonane 64.62
    1-hexene 7.28
    2-isopropoxyethanol 72.52
    2,2,2-trifluoroethanol 61.41
    methyl butyrate 23.73

    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