2-(Acetoacetoxy)ethyl methacrylate

Overview IFRA Request a quote

  • Identifiers

    CAS number
    21282-96-2

    Molecular formula
    C10H14O5

    SMILES
    CC(=C)C(=O)OCCOC(=O)CC(=O)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 76.57%
    Caramellic 63.86%
    Sweet 50.58%
    Winey 50.39%
    Apple 36.38%
    Ethereal 36.33%
    Burnt 36.2%
    Buttery 32.64%
    Rummy 31.14%
    Creamy 28.92%

     

    Flavor
    Fruity 81.88%
    Floral 32.11%
    Creamy 31.94%
    Berry 29.45%
    Sweet 28.58%
    Green 28.38%
    Tropical 28.16%
    Fatty 27.34%
    Grape 26.62%
    Mild 26.19%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    7.04 (neutral)

    Molecular weight
    214.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    298°C

    Flash point

    • 134.68 ˚C est.

  • Synonyms

    • 2-(Methacryloyloxy)ethyl acetoacetate
    • Eastman AAEM
    • 2-(acetoacetoxy)ethyl methacrylate
    • LONZAMON AAEMA
    • 6L3EW3HZF2
    • DTXSID7041388
    • UNII-6L3EW3HZF2
    • DTXCID5021388
    • 2-((2-Methyl-1-oxoallyl)oxy)ethyl acetoacetate
    • EINECS 244-311-1
    • ACETOACETOXYETHOXY METHACRYLATE
    • 2-hydroxyethyl methacrylate acetoacetate
    • Butanoic acid, 3-oxo-, 2-((2-methyl-1-oxo-2-propenyl)oxy)ethyl ester
    • Butanoic acid, 3-oxo-, 2-((2-methyl-1-oxo-2-propen-1-yl)oxy)ethyl ester
    • EC 244-311-1
    • ETHYLENE GLYCOL ACETOACETATE METHACRYLATE
    • Acetoacetic acid, 2-hydroxyethyl ester methacrylate
    • 2-[(2-METHYL-1-OXOALLYL)OXY]ETHYL ACETOACETATE
    • 2-[Methacryloyloxy]ethyl acetoacetate
    • Butanoic acid, 3-oxo-, 2-[(2-methyl-1-oxo-2-propen-1-yl)oxy]ethyl ester
    • Butanoic acid, 3-oxo-, 2-[(2-methyl-1-oxo-2-propenyl)oxy]ethyl ester
    • RefChem:84542
    • ACETOACETOXYETHOXY METHACRYLATE [INCI]
    • 620-986-1
    • 21282-96-2
    • 21282-97-3
    • 2-(methacryloyloxy)ethyl 3-oxobutanoate
    • AAEM
    • Ethylene glycol monoacetoacetate monomethacrylate
    • 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate
    • acetoacetoxyethyl methacrylate
    • MFCD00054405
    • (2-Acetoacetoxy)ethyl methacrylate
    • 2-[(2-METHYLPROP-2-ENOYL)OXY]ETHYL 3-OXOBUTANOATE
    • 2-(Acetoacetyloxy)ethyl Methacrylate
    • Methacrylic Acid 2-(Acetoacetyloxy)ethyl Ester
    • Acetoacetic Acid 2-(Methacryloyloxy)ethyl Ester
    • 2-[(2-methylacryloyl)oxy]ethyl 3-oxobutanoate
    • HEMA ACETOACETATE
    • 2-(methacryloyloxy)ethylacetoacetate
    • SCHEMBL62134
    • CHEMBL3188313
    • 3-OXO-BUTYRIC ACID 2-(2-METHYLACRYLOYLOXY)ETHYL ESTER
    • BB_SC-05603
    • Tox21_301183
    • BBL028062
    • STL382158
    • AKOS015903117
    • CS-W014943
    • FE60059
    • NCGC00248321-01
    • NCGC00255081-01
    • AS-64020
    • SY057389
    • CAS-21282-97-3
    • 2-(Methacryloyloxy)ethyl acetoacetate, 95%
    • E0489
    • NS00005384
    • F85630
    • F241539
    • Q27265080
    • 2-(Methacryloyloxy)ethyl 3-oxobutanoate (stabilised with BHT)
    • Ethylene Glycol Monoacetoacetate Monomethacrylate (stabilized with BHT)
    • Ethylene Glycol Monoacetoacetate Monomethacrylate, (stabilized with BHT)
    • 65188-70-7
    • 21282-97-3

  • Applications

    2-(Acetoacetoxy)ethyl methacrylate (CAS 21282-96-2) is a bifunctional monomer used primarily in coatings, adhesives, and polymer resins, providing a methacrylate group for UV or thermal polymerization and an acetoacetoxy group that enables crosslinking after heating or with amines/aldehydes. Typical applications include UV-curable coatings and inks, adhesives and sealants with enhanced crosslinking and mechanical performance, resins and plastics formulations incorporating thermally or UV-crosslinkable networks, electronics encapsulants or resins for potting and protection, and industrial coating systems for metal and wood substrates.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 144.41
    methanol 220.56
    isopropanol 116.81
    water 4.0
    ethyl acetate 119.56
    n-propanol 89.5
    acetone 389.13
    n-butanol 76.15
    acetonitrile 212.16
    DMF 734.2
    toluene 28.51
    isobutanol 72.01
    1,4-dioxane 182.14
    methyl acetate 174.63
    THF 322.26
    2-butanone 198.69
    n-pentanol 70.03
    sec-butanol 105.74
    n-hexane 5.86
    ethylene glycol 42.14
    NMP 668.93
    cyclohexane 2.73
    DMSO 832.97
    n-butyl acetate 62.19
    n-octanol 26.53
    chloroform 198.79
    n-propyl acetate 75.31
    acetic acid 390.65
    dichloromethane 271.98
    cyclohexanone 210.67
    propylene glycol 50.05
    isopropyl acetate 74.13
    DMAc 890.53
    2-ethoxyethanol 220.37
    isopentanol 83.29
    n-heptane 1.97
    ethyl formate 128.91
    1,2-dichloroethane 169.68
    n-hexanol 39.05
    2-methoxyethanol 334.15
    isobutyl acetate 44.07
    tetrachloromethane 12.96
    n-pentyl acetate 31.91
    transcutol 376.13
    n-heptanol 15.92
    ethylbenzene 33.16
    MIBK 88.81
    2-propoxyethanol 128.97
    tert-butanol 215.75
    MTBE 122.13
    2-butoxyethanol 50.98
    propionic acid 128.33
    o-xylene 36.12
    formic acid 199.29
    diethyl ether 86.68
    m-xylene 26.21
    p-xylene 44.62
    chlorobenzene 55.53
    dimethyl carbonate 72.48
    n-octane 1.36
    formamide 293.46
    cyclopentanone 270.51
    2-pentanone 134.49
    anisole 109.38
    cyclopentyl methyl ether 106.2
    gamma-butyrolactone 368.0
    1-methoxy-2-propanol 205.13
    pyridine 128.94
    3-pentanone 103.86
    furfural 331.41
    n-dodecane 1.79
    diethylene glycol 125.2
    diisopropyl ether 20.05
    tert-amyl alcohol 175.66
    acetylacetone 209.79
    n-hexadecane 1.99
    acetophenone 130.14
    methyl propionate 122.63
    isopentyl acetate 61.34
    trichloroethylene 295.46
    n-nonanol 24.94
    cyclohexanol 71.04
    benzyl alcohol 90.06
    2-ethylhexanol 27.16
    isooctanol 15.57
    dipropyl ether 30.73
    1,2-dichlorobenzene 65.73
    ethyl lactate 57.74
    propylene carbonate 173.95
    n-methylformamide 286.69
    2-pentanol 54.36
    n-pentane 3.14
    1-propoxy-2-propanol 76.66
    1-methoxy-2-propyl acetate 86.49
    2-(2-methoxypropoxy) propanol 118.41
    mesitylene 15.81
    ε-caprolactone 193.16
    p-cymene 16.53
    epichlorohydrin 362.38
    1,1,1-trichloroethane 99.35
    2-aminoethanol 75.81
    morpholine-4-carbaldehyde 444.17
    sulfolane 516.41
    2,2,4-trimethylpentane 4.0
    2-methyltetrahydrofuran 194.42
    n-hexyl acetate 63.32
    isooctane 1.95
    2-(2-butoxyethoxy)ethanol 121.74
    sec-butyl acetate 54.79
    tert-butyl acetate 98.24
    decalin 5.62
    glycerin 100.17
    diglyme 227.18
    acrylic acid 131.38
    isopropyl myristate 27.02
    n-butyric acid 130.7
    acetyl acetate 94.48
    di(2-ethylhexyl) phthalate 33.96
    ethyl propionate 83.71
    nitromethane 715.07
    1,2-diethoxyethane 87.37
    benzonitrile 92.49
    trioctyl phosphate 20.89
    1-bromopropane 77.56
    gamma-valerolactone 398.42
    n-decanol 19.23
    triethyl phosphate 42.5
    4-methyl-2-pentanol 34.77
    propionitrile 98.42
    vinylene carbonate 155.26
    1,1,2-trichlorotrifluoroethane 246.89
    DMS 78.73
    cumene 25.84
    2-octanol 14.89
    2-hexanone 98.05
    octyl acetate 34.15
    limonene 23.79
    1,2-dimethoxyethane 362.41
    ethyl orthosilicate 36.65
    tributyl phosphate 33.35
    diacetone alcohol 161.26
    N,N-dimethylaniline 90.67
    acrylonitrile 144.77
    aniline 65.89
    1,3-propanediol 117.96
    bromobenzene 46.03
    dibromomethane 146.68
    1,1,2,2-tetrachloroethane 229.08
    2-methyl-cyclohexyl acetate 57.86
    tetrabutyl urea 50.99
    diisobutyl methanol 17.88
    2-phenylethanol 56.89
    styrene 37.85
    dioctyl adipate 51.53
    dimethyl sulfate 203.72
    ethyl butyrate 59.42
    methyl lactate 85.95
    butyl lactate 39.92
    diethyl carbonate 47.26
    propanediol butyl ether 72.82
    triethyl orthoformate 44.37
    p-tert-butyltoluene 15.03
    methyl 4-tert-butylbenzoate 84.5
    morpholine 252.7
    tert-butylamine 84.96
    n-dodecanol 14.92
    dimethoxymethane 251.66
    ethylene carbonate 111.58
    cyrene 142.69
    2-ethoxyethyl acetate 62.39
    2-ethylhexyl acetate 45.0
    1,2,4-trichlorobenzene 87.74
    4-methylpyridine 186.87
    dibutyl ether 37.12
    2,6-dimethyl-4-heptanol 17.88
    DEF 213.84
    dimethyl isosorbide 182.59
    tetrachloroethylene 104.81
    eugenol 79.39
    triacetin 96.71
    span 80 68.26
    1,4-butanediol 57.44
    1,1-dichloroethane 125.05
    2-methyl-1-pentanol 79.26
    methyl formate 231.27
    2-methyl-1-butanol 80.29
    n-decane 2.89
    butyronitrile 91.79
    3,7-dimethyl-1-octanol 34.59
    1-chlorooctane 15.62
    1-chlorotetradecane 7.03
    n-nonane 2.54
    undecane 2.22
    tert-butylcyclohexane 5.42
    cyclooctane 1.18
    cyclopentanol 84.26
    tetrahydropyran 120.11
    tert-amyl methyl ether 105.03
    2,5,8-trioxanonane 172.44
    1-hexene 28.34
    2-isopropoxyethanol 124.48
    2,2,2-trifluoroethanol 137.37
    methyl butyrate 121.01

    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