Diethyl acetoxymalonate

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  • Identifiers

    CAS number
    5468-23-5

    Molecular formula
    C9H14O6

    SMILES
    CCOC(=O)C(C(=O)OCC)OC(=O)C

    Safety labels

  • Odor profile

    Fragrance
    Fruity 83.24%
    Winey 58.46%
    Apple 52.93%
    Caramellic 46.87%
    Sweet 38.62%
    Green 36.84%
    Ethereal 34.89%
    Herbal 33.0%
    Tropical 32.52%
    Buttery 29.51%

     

    Flavor
    Fruity 72.74%
    Mild 43.26%
    Bitter 40.07%
    Wine 31.66%
    Creamy 31.21%
    Odorless 29.6%
    Grape 29.09%
    Green 26.53%
    Fruit 25.66%
    Buttery 25.25%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    4.72 (weak acid)

    Molecular weight
    218.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    258°C

    Flash point

    • 109.04 ˚C est.

  • Synonyms

    • Diethyl acetoxymalonate
    • 5468-23-5
    • DIETHYL (ACETYLOXY)MALONATE
    • diethyl 2-acetyloxypropanedioate
    • MFCD00039895
    • 1,3-diethyl 2-(acetyloxy)propanedioate
    • EINECS 226-786-7
    • diethyl 2-acetoxypropanedioate
    • Diethyl (acetyloxy)propanedioate
    • SCHEMBL29103901
    • XZFLUEMBCUUTKI-UHFFFAOYSA-
    • Acetoxymalonic Acid Diethyl Ester
    • DTXSID40203134
    • XZFLUEMBCUUTKI-UHFFFAOYSA-N
    • NSC25377
    • NSC 25377
    • NSC-25377
    • SBB080594
    • AKOS005110982
    • diethyl 2-acetyloxypropane-1,3-dioate
    • Tartronic acid, diethyl ester, acetate
    • DB-052631
    • NS00033170
    • InChI=1/C9H14O6/c1-4-13-8(11)7(15-6(3)10)9(12)14-5-2/h7H,4-5H2,1-3H3
    • 5468-23-5

  • Applications

    Diethyl acetoxymalonate (CAS 5468-23-5) is a diethyl malonate derivative with an acetoxy group at the alpha position, primarily used as an intermediate in organic synthesis due to the methylene-activated center and its participation in carbon–carbon bond-forming reactions (alkylation, condensations) to build more complex molecules. It serves as a building block for β-dicarbonyl derivatives and common heterocycles such as pyridines and pyrazoles via typical malonate chemistry. It is commonly employed as an intermediate in the synthesis of pharmaceutical and agrochemical compounds. Additionally, it may be evaluated for fragrance and aroma applications as a precursor to aroma-active compounds. It also has potential as a building block for malonate-derived polymers and plastics in materials science.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 49.95
    methanol 89.44
    isopropanol 31.45
    water 2.53
    ethyl acetate 41.98
    n-propanol 29.86
    acetone 105.54
    n-butanol 26.98
    acetonitrile 47.9
    DMF 291.39
    toluene 45.18
    isobutanol 21.97
    1,4-dioxane 142.36
    methyl acetate 71.25
    THF 197.8
    2-butanone 58.17
    n-pentanol 20.93
    sec-butanol 24.19
    n-hexane 4.72
    ethylene glycol 29.75
    NMP 538.28
    cyclohexane 12.36
    DMSO 362.32
    n-butyl acetate 37.48
    n-octanol 9.96
    chloroform 110.95
    n-propyl acetate 30.08
    acetic acid 109.35
    dichloromethane 148.9
    cyclohexanone 135.09
    propylene glycol 17.55
    isopropyl acetate 27.67
    DMAc 372.72
    2-ethoxyethanol 57.85
    isopentanol 24.1
    n-heptane 2.68
    ethyl formate 58.49
    1,2-dichloroethane 118.4
    n-hexanol 17.64
    2-methoxyethanol 120.6
    isobutyl acetate 19.67
    tetrachloromethane 18.69
    n-pentyl acetate 19.91
    transcutol 84.89
    n-heptanol 8.85
    ethylbenzene 27.14
    MIBK 26.36
    2-propoxyethanol 57.45
    tert-butanol 45.08
    MTBE 32.74
    2-butoxyethanol 28.24
    propionic acid 45.74
    o-xylene 41.97
    formic acid 100.16
    diethyl ether 29.46
    m-xylene 27.34
    p-xylene 38.37
    chlorobenzene 62.17
    dimethyl carbonate 48.15
    n-octane 1.46
    formamide 142.85
    cyclopentanone 169.53
    2-pentanone 37.06
    anisole 49.21
    cyclopentyl methyl ether 60.26
    gamma-butyrolactone 226.05
    1-methoxy-2-propanol 57.75
    pyridine 147.72
    3-pentanone 37.82
    furfural 279.41
    n-dodecane 1.52
    diethylene glycol 64.38
    diisopropyl ether 8.45
    tert-amyl alcohol 35.34
    acetylacetone 72.67
    n-hexadecane 1.75
    acetophenone 64.11
    methyl propionate 51.41
    isopentyl acetate 37.9
    trichloroethylene 177.73
    n-nonanol 10.36
    cyclohexanol 43.6
    benzyl alcohol 50.81
    2-ethylhexanol 14.62
    isooctanol 8.12
    dipropyl ether 16.39
    1,2-dichlorobenzene 63.28
    ethyl lactate 24.51
    propylene carbonate 119.54
    n-methylformamide 112.97
    2-pentanol 13.72
    n-pentane 3.75
    1-propoxy-2-propanol 32.41
    1-methoxy-2-propyl acetate 44.09
    2-(2-methoxypropoxy) propanol 44.15
    mesitylene 17.76
    ε-caprolactone 121.77
    p-cymene 16.91
    epichlorohydrin 200.07
    1,1,1-trichloroethane 65.08
    2-aminoethanol 34.45
    morpholine-4-carbaldehyde 278.91
    sulfolane 342.58
    2,2,4-trimethylpentane 2.93
    2-methyltetrahydrofuran 112.78
    n-hexyl acetate 25.94
    isooctane 1.5
    2-(2-butoxyethoxy)ethanol 43.53
    sec-butyl acetate 20.7
    tert-butyl acetate 35.29
    decalin 8.95
    glycerin 43.58
    diglyme 93.63
    acrylic acid 62.54
    isopropyl myristate 12.46
    n-butyric acid 49.62
    acetyl acetate 46.84
    di(2-ethylhexyl) phthalate 22.11
    ethyl propionate 32.38
    nitromethane 193.42
    1,2-diethoxyethane 30.81
    benzonitrile 61.36
    trioctyl phosphate 13.19
    1-bromopropane 39.2
    gamma-valerolactone 254.33
    n-decanol 8.3
    triethyl phosphate 31.59
    4-methyl-2-pentanol 10.25
    propionitrile 34.05
    vinylene carbonate 111.64
    1,1,2-trichlorotrifluoroethane 173.95
    DMS 50.79
    cumene 18.75
    2-octanol 6.39
    2-hexanone 30.68
    octyl acetate 16.34
    limonene 21.69
    1,2-dimethoxyethane 126.11
    ethyl orthosilicate 27.89
    tributyl phosphate 18.9
    diacetone alcohol 43.97
    N,N-dimethylaniline 50.75
    acrylonitrile 56.52
    aniline 59.11
    1,3-propanediol 50.85
    bromobenzene 61.59
    dibromomethane 88.9
    1,1,2,2-tetrachloroethane 151.65
    2-methyl-cyclohexyl acetate 38.23
    tetrabutyl urea 32.96
    diisobutyl methanol 10.15
    2-phenylethanol 40.63
    styrene 32.49
    dioctyl adipate 26.01
    dimethyl sulfate 119.15
    ethyl butyrate 31.18
    methyl lactate 41.81
    butyl lactate 20.86
    diethyl carbonate 29.9
    propanediol butyl ether 23.92
    triethyl orthoformate 28.99
    p-tert-butyltoluene 15.34
    methyl 4-tert-butylbenzoate 44.75
    morpholine 149.54
    tert-butylamine 25.95
    n-dodecanol 6.86
    dimethoxymethane 103.96
    ethylene carbonate 87.15
    cyrene 79.24
    2-ethoxyethyl acetate 32.78
    2-ethylhexyl acetate 32.72
    1,2,4-trichlorobenzene 83.92
    4-methylpyridine 139.29
    dibutyl ether 13.83
    2,6-dimethyl-4-heptanol 10.15
    DEF 93.08
    dimethyl isosorbide 100.56
    tetrachloroethylene 114.29
    eugenol 44.58
    triacetin 37.89
    span 80 31.64
    1,4-butanediol 20.75
    1,1-dichloroethane 59.82
    2-methyl-1-pentanol 21.88
    methyl formate 114.21
    2-methyl-1-butanol 23.22
    n-decane 2.26
    butyronitrile 32.77
    3,7-dimethyl-1-octanol 12.44
    1-chlorooctane 8.39
    1-chlorotetradecane 4.79
    n-nonane 1.97
    undecane 1.82
    tert-butylcyclohexane 5.14
    cyclooctane 3.55
    cyclopentanol 55.48
    tetrahydropyran 83.5
    tert-amyl methyl ether 30.97
    2,5,8-trioxanonane 76.66
    1-hexene 13.35
    2-isopropoxyethanol 32.21
    2,2,2-trifluoroethanol 65.13
    methyl butyrate 48.82

    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