N-(1,1-Dimethyl-3-oxobutyl)acrylamide

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  • Identifiers

    CAS number
    2873-97-4

    Molecular formula
    C9H15NO2

    SMILES
    CC(=O)CC(C)(C)NC(=O)C=C

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Fruity 45.36%
    Mint 33.09%
    Grape 30.82%
    Citrus 30.14%
    Meaty 29.31%
    Grapefruit 27.34%
    Fresh 25.71%
    Herbal 25.66%
    Sweet 25.59%
    Woody 24.9%

     

    Flavor
    Fruity 40.4%
    Berry 23.11%
    Stinky 19.94%
    Light 19.87%
    Ocimene 19.87%
    Cat-urine 19.81%
    Mouldy 19.73%
    Acrid 19.65%
    Matches 19.3%
    Box tree 19.22%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    8.3 (weak base)

    Molecular weight
    169.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 135 to 136 °F (NTP, 1992)
    • 57-58 °C

    Boiling point

    • 248 °F at 8 mmHg (NTP, 1992)
    • 120 °C @ 8 mm Hg

    Flash point

    • 111.2 ˚C est.

    Solubility expt.

    • Very soluble (NTP, 1992)
    • Highly sol in water and most organic solvents
    • Soluble in chloroform

  • Synonyms

    • N-(1,1-Dimethyl-3-oxobutyl)acrylamide
    • DAAm compound
    • RefChem:586138
    • DIACETONE ACRYLAMIDE
    • 2873-97-4
    • N-(2-Methyl-4-oxopentan-2-yl)acrylamide
    • Diacetoneacrylamide
    • 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-
    • N-(2-methyl-4-oxopentan-2-yl)prop-2-enamide
    • N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide
    • Acrylamide, N-(1,1-dimethyl-3-oxobutyl)-
    • N-(2-(2-Methyl-4-oxopentyl))acrylamide
    • DTXSID1024916
    • MFCD00008788
    • 3Z8J3430Z2
    • NSC-130565
    • Acrylamide, N,N-diacetonyl-
    • CCRIS 5898
    • HSDB 4278
    • EINECS 220-713-2
    • NSC 130565
    • BRN 1928444
    • 2-Propenamide, N,N-bis(2-oxopropyl)-
    • UNII-3Z8J3430Z2
    • diacetonylacrylamide
    • diacetone-acrylamide
    • DAAA
    • Acrylamide,N-diacetonyl-
    • EC 220-713-2
    • SCHEMBL35470
    • DTXCID904916
    • CHEMBL3183854
    • DIACETONE ACRYLAMIDE [MI]
    • DIACETONE ACRYLAMIDE [HSDB]
    • WLN: 1V1X1&1&MV1U1
    • 2-Propenamide,N-bis(2-oxopropyl)-
    • Acrylamide,1-dimethyl-3-oxobutyl)-
    • Tox21_302117
    • NSC130565
    • STK084883
    • AKOS000121256
    • CS-W017721
    • DS-8583
    • FD36857
    • 2-Propenamide,1-dimethyl-3-oxobutyl)-
    • n-(1,1-dimethyl-3-oxybutyl)acrylamide
    • NCGC00255301-01
    • CAS-2873-97-4
    • D0062
    • D5845
    • Diacetone Acrylamide (stabilized with MEHQ)
    • N-(1,1-dimethyl-3-oxobutyl)prop-2-enamide
    • NS00011495
    • ST45025448
    • Diacetone Acrylamide, (stabilized with MEHQ)
    • EN300-21111
    • N-(1,1-dimethyl-3-oxo-butyl)prop-2-enamide
    • E76525
    • F464552
    • Q27258255
    • Z104492162
    • Diacetone acrylamide, contains <=100 ppm inhibitor, 99%
    • InChI=1/C9H15NO2/c1-5-8(12)10-9(3,4)6-7(2)11/h5H,1,6H2,2-4H3,(H,10,12
    • 2873-97-4

  • Applications

    N-(1,1-Dimethyl-3-oxobutyl)acrylamide (CAS 2873-97-4) is primarily used as a functional monomer and synthetic intermediate in polymer and resin applications. In industrial manufacturing, it can be copolymerized with other vinyl monomers to form functional polymers and coatings, where the acrylamide backbone provides polarity and processability and the ketone-bearing side chain enables post-polymerization modification. The carbonyl functionality supports crosslinking via hydrazone, oxime, or amine chemistries, enabling durable coatings, adhesives, and printed inks with enhanced solvent resistance. It also serves as a building block for specialty polymers and resins aimed at tailored glass-transition temperatures and thermal stability for high-performance plastics. Additionally, it may function as an intermediate in hydrogel or polymer-network formulations used in electronics packaging, filtration, or separation technologies, subject to formulation constraints and regulatory considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 884.53
    methanol 1540.53
    isopropanol 601.99
    water 71.5
    ethyl acetate 563.91
    n-propanol 722.27
    acetone 953.02
    n-butanol 549.35
    acetonitrile 441.69
    DMF 1490.64
    toluene 205.19
    isobutanol 561.32
    1,4-dioxane 406.43
    methyl acetate 762.38
    THF 1122.22
    2-butanone 776.81
    n-pentanol 392.41
    sec-butanol 628.61
    n-hexane 58.09
    ethylene glycol 277.77
    NMP 1742.16
    cyclohexane 40.42
    DMSO 621.78
    n-butyl acetate 246.65
    n-octanol 187.93
    chloroform 517.06
    n-propyl acetate 264.96
    acetic acid 1456.01
    dichloromethane 392.37
    cyclohexanone 887.46
    propylene glycol 517.51
    isopropyl acetate 323.23
    DMAc 1822.73
    2-ethoxyethanol 456.92
    isopentanol 413.13
    n-heptane 22.58
    ethyl formate 570.7
    1,2-dichloroethane 271.61
    n-hexanol 503.86
    2-methoxyethanol 908.16
    isobutyl acetate 182.25
    tetrachloromethane 78.21
    n-pentyl acetate 155.09
    transcutol 579.44
    n-heptanol 150.07
    ethylbenzene 102.29
    MIBK 330.6
    2-propoxyethanol 607.2
    tert-butanol 641.47
    MTBE 462.09
    2-butoxyethanol 217.47
    propionic acid 984.3
    o-xylene 159.0
    formic acid 803.86
    diethyl ether 400.76
    m-xylene 184.65
    p-xylene 126.93
    chlorobenzene 212.74
    dimethyl carbonate 229.22
    n-octane 9.24
    formamide 425.41
    cyclopentanone 993.63
    2-pentanone 592.78
    anisole 195.92
    cyclopentyl methyl ether 637.68
    gamma-butyrolactone 1209.04
    1-methoxy-2-propanol 626.77
    pyridine 440.94
    3-pentanone 445.24
    furfural 759.04
    n-dodecane 7.02
    diethylene glycol 382.59
    diisopropyl ether 104.86
    tert-amyl alcohol 648.1
    acetylacetone 501.87
    n-hexadecane 7.66
    acetophenone 238.56
    methyl propionate 574.93
    isopentyl acetate 216.96
    trichloroethylene 587.0
    n-nonanol 144.37
    cyclohexanol 560.22
    benzyl alcohol 249.41
    2-ethylhexanol 197.02
    isooctanol 106.17
    dipropyl ether 126.15
    1,2-dichlorobenzene 156.29
    ethyl lactate 158.17
    propylene carbonate 573.45
    n-methylformamide 889.95
    2-pentanol 385.65
    n-pentane 51.77
    1-propoxy-2-propanol 296.03
    1-methoxy-2-propyl acetate 265.99
    2-(2-methoxypropoxy) propanol 180.74
    mesitylene 85.94
    ε-caprolactone 829.2
    p-cymene 55.55
    epichlorohydrin 769.65
    1,1,1-trichloroethane 290.54
    2-aminoethanol 514.45
    morpholine-4-carbaldehyde 880.08
    sulfolane 935.11
    2,2,4-trimethylpentane 31.98
    2-methyltetrahydrofuran 954.32
    n-hexyl acetate 320.83
    isooctane 16.76
    2-(2-butoxyethoxy)ethanol 231.7
    sec-butyl acetate 187.26
    tert-butyl acetate 305.29
    decalin 28.58
    glycerin 536.74
    diglyme 339.21
    acrylic acid 800.8
    isopropyl myristate 71.74
    n-butyric acid 901.85
    acetyl acetate 296.4
    di(2-ethylhexyl) phthalate 93.53
    ethyl propionate 260.29
    nitromethane 1389.17
    1,2-diethoxyethane 143.96
    benzonitrile 241.73
    trioctyl phosphate 69.64
    1-bromopropane 235.66
    gamma-valerolactone 1140.06
    n-decanol 89.94
    triethyl phosphate 77.28
    4-methyl-2-pentanol 185.56
    propionitrile 365.35
    vinylene carbonate 504.56
    1,1,2-trichlorotrifluoroethane 617.46
    DMS 222.29
    cumene 75.76
    2-octanol 109.91
    2-hexanone 321.4
    octyl acetate 109.61
    limonene 94.92
    1,2-dimethoxyethane 498.94
    ethyl orthosilicate 75.8
    tributyl phosphate 87.98
    diacetone alcohol 419.75
    N,N-dimethylaniline 151.74
    acrylonitrile 432.56
    aniline 334.19
    1,3-propanediol 522.82
    bromobenzene 145.57
    dibromomethane 264.18
    1,1,2,2-tetrachloroethane 442.8
    2-methyl-cyclohexyl acetate 141.76
    tetrabutyl urea 116.55
    diisobutyl methanol 62.7
    2-phenylethanol 228.81
    styrene 108.54
    dioctyl adipate 103.69
    dimethyl sulfate 358.12
    ethyl butyrate 149.54
    methyl lactate 320.64
    butyl lactate 150.33
    diethyl carbonate 90.69
    propanediol butyl ether 263.8
    triethyl orthoformate 99.69
    p-tert-butyltoluene 52.84
    methyl 4-tert-butylbenzoate 181.87
    morpholine 681.1
    tert-butylamine 317.15
    n-dodecanol 56.69
    dimethoxymethane 549.93
    ethylene carbonate 418.65
    cyrene 250.57
    2-ethoxyethyl acetate 200.73
    2-ethylhexyl acetate 172.71
    1,2,4-trichlorobenzene 210.74
    4-methylpyridine 685.14
    dibutyl ether 104.35
    2,6-dimethyl-4-heptanol 62.7
    DEF 675.37
    dimethyl isosorbide 272.95
    tetrachloroethylene 286.0
    eugenol 157.18
    triacetin 225.18
    span 80 178.12
    1,4-butanediol 241.16
    1,1-dichloroethane 379.74
    2-methyl-1-pentanol 328.57
    methyl formate 766.44
    2-methyl-1-butanol 532.08
    n-decane 15.01
    butyronitrile 396.01
    3,7-dimethyl-1-octanol 137.1
    1-chlorooctane 77.13
    1-chlorotetradecane 20.6
    n-nonane 15.49
    undecane 9.93
    tert-butylcyclohexane 30.69
    cyclooctane 16.35
    cyclopentanol 640.32
    tetrahydropyran 640.95
    tert-amyl methyl ether 410.05
    2,5,8-trioxanonane 205.01
    1-hexene 181.35
    2-isopropoxyethanol 288.52
    2,2,2-trifluoroethanol 468.88
    methyl butyrate 365.7

    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