Benzyl acetoacetate

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  • Identifiers

    CAS number
    5396-89-4

    Molecular formula
    C11H12O3

    SMILES
    CC(=O)CC(=O)OCC1=CC=CC=C1

  • Odor profile

    Fragrance
    Fruity 90.72%
    Sweet 79.34%
    Floral 63.37%
    Balsamic 55.12%
    Caramellic 46.55%
    Spicy 44.59%
    Honey 44.49%
    Berry 38.68%
    Cherry 36.15%
    Winey 35.11%

     

    Flavor
    Sweet 87.26%
    Fruity 85.46%
    Floral 71.89%
    Berry 36.46%
    Balsam 35.92%
    Cherry 34.4%
    Fresh 34.04%
    Grape 31.91%
    Spicy 31.35%
    Strawberry 31.21%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    7.78 (neutral)

    Molecular weight
    192.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 162.00 to 164.00 °C. @ 16.00 mm Hg

    Boiling point

    • 156.00 to 159.00 °C. @ 10.00 mm Hg

    Flash point

    • 134.79 ˚C est.

    Solubility expt.

    • insoluble in water; soluble in organic solvents, oils
    • miscible at room temperature (in ethanol)

  • Synonyms

    • Benzyl acetoacetate
    • Benzyl 3-oxobutanoate
    • 5396-89-4
    • Acetoacetic acid benzyl ester
    • Benzyl acetylacetate
    • Acetoacetic acid, benzyl ester
    • Phenylmethyl 3-oxobutanoate
    • Butanoic acid, 3-oxo-, phenylmethyl ester
    • AC-benzyl
    • Benzyl beta-ketobutyrate
    • FEMA No. 2136
    • UNII-F9S0XGV18X
    • NSC 4391
    • F9S0XGV18X
    • MFCD00008785
    • NSC-4391
    • EINECS 226-416-4
    • AI3-06229
    • DTXSID8063834
    • FEMA 2136
    • WOFAGNLBCJWEOE-UHFFFAOYSA-
    • BENZYL ACETOACETATE [FHFI]
    • Acetoacetic acid, benzyl ester (8CI)
    • 3-OXOBUTANOIC ACID BENZYL ESTER
    • 38432-58-5
    • 3-OXOBUTANOIC ACID PHENYLMETHYL ESTER
    • BENZYLACETOACETATE
    • benzyl3-oxobutanoate
    • Benzyl acetoacetic acid
    • Benzyl 3-oxobutanoic acid
    • Benzyl acetoacetate, 97%
    • SCHEMBL26569
    • DTXCID1041552
    • 3-oxo-butanoicaciphenylmethylester
    • NSC4391
    • CHEBI:173928
    • BCP23315
    • BBL027729
    • STL373489
    • AKOS000119530
    • AS-47647
    • Butanoic acid, 3-oxo, phenylmethyl ester
    • SY015679
    • DB-002129
    • A1080
    • CS-0071955
    • NS00012000
    • EN300-21320
    • F14832
    • Benzyl acetoacetate, Lonza quality, >=96.0% (GC)
    • Q27277858
    • F0001-1407
    • Z104495340
    • Benzyl acetoacetate, produced by Wacker Chemie AG, Burghausen, Germany, >=96% (GC)
    • 226-416-4
    • 3-Oxobutanoic Acid Benzyl Ester; 3-Oxobutanoic Acid Phenylmethyl Este;Benzyl 3-Oxobutanoate; Benzyl 3-Oxobutyrate

  • Applications

    Benzyl acetoacetate is a versatile beta-dicarbonyl ester primarily used as an organic synthesis intermediate. It acts as an enolate nucleophile in alkylations and participates in Knoevenagel and Michael-type condensations to furnish substituted beta-dicarbonyl building blocks. In practice, it is used as a precursor for fragrance and flavor ingredients, pharmaceutical intermediates, and components for specialty polymers or coatings; it may also appear in cosmetic/personal-care formulation workflows as a precursor for fragrance-related or functional ingredients, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 221.19
    methanol 312.84
    isopropanol 157.66
    water 3.22
    ethyl acetate 87.59
    n-propanol 136.85
    acetone 362.27
    n-butanol 101.34
    acetonitrile 176.62
    DMF 809.28
    toluene 12.43
    isobutanol 89.35
    1,4-dioxane 266.28
    methyl acetate 161.05
    THF 346.02
    2-butanone 172.6
    n-pentanol 73.82
    sec-butanol 98.37
    n-hexane 1.76
    ethylene glycol 157.7
    NMP 345.27
    cyclohexane 1.53
    DMSO 871.7
    n-butyl acetate 51.99
    n-octanol 31.9
    chloroform 233.05
    n-propyl acetate 58.77
    acetic acid 291.06
    dichloromethane 153.52
    cyclohexanone 143.35
    propylene glycol 245.23
    isopropyl acetate 54.0
    DMAc 765.61
    2-ethoxyethanol 230.93
    isopentanol 92.24
    n-heptane 1.28
    ethyl formate 75.24
    1,2-dichloroethane 105.13
    n-hexanol 55.6
    2-methoxyethanol 445.51
    isobutyl acetate 44.49
    tetrachloromethane 10.81
    n-pentyl acetate 26.74
    transcutol 705.13
    n-heptanol 24.06
    ethylbenzene 16.8
    MIBK 73.09
    2-propoxyethanol 171.93
    tert-butanol 192.33
    MTBE 75.15
    2-butoxyethanol 79.98
    propionic acid 159.84
    o-xylene 16.17
    formic acid 167.74
    diethyl ether 58.24
    m-xylene 15.3
    p-xylene 24.42
    chlorobenzene 37.23
    dimethyl carbonate 86.23
    n-octane 0.76
    formamide 233.94
    cyclopentanone 225.85
    2-pentanone 97.13
    anisole 96.3
    cyclopentyl methyl ether 79.58
    gamma-butyrolactone 241.48
    1-methoxy-2-propanol 294.17
    pyridine 109.79
    3-pentanone 73.68
    furfural 235.92
    n-dodecane 1.5
    diethylene glycol 226.25
    diisopropyl ether 13.61
    tert-amyl alcohol 115.34
    acetylacetone 172.45
    n-hexadecane 1.7
    acetophenone 87.36
    methyl propionate 110.26
    isopentyl acetate 55.6
    trichloroethylene 232.04
    n-nonanol 28.61
    cyclohexanol 60.42
    benzyl alcohol 82.13
    2-ethylhexanol 32.21
    isooctanol 22.02
    dipropyl ether 30.27
    1,2-dichlorobenzene 50.43
    ethyl lactate 69.44
    propylene carbonate 124.62
    n-methylformamide 258.26
    2-pentanol 51.91
    n-pentane 0.87
    1-propoxy-2-propanol 107.25
    1-methoxy-2-propyl acetate 97.1
    2-(2-methoxypropoxy) propanol 141.17
    mesitylene 11.69
    ε-caprolactone 115.25
    p-cymene 14.13
    epichlorohydrin 274.58
    1,1,1-trichloroethane 78.24
    2-aminoethanol 216.37
    morpholine-4-carbaldehyde 357.52
    sulfolane 322.65
    2,2,4-trimethylpentane 2.09
    2-methyltetrahydrofuran 140.83
    n-hexyl acetate 59.42
    isooctane 1.73
    2-(2-butoxyethoxy)ethanol 174.73
    sec-butyl acetate 42.41
    tert-butyl acetate 74.29
    decalin 3.55
    glycerin 315.78
    diglyme 303.31
    acrylic acid 169.48
    isopropyl myristate 25.25
    n-butyric acid 120.69
    acetyl acetate 74.61
    di(2-ethylhexyl) phthalate 37.06
    ethyl propionate 60.48
    nitromethane 525.94
    1,2-diethoxyethane 89.79
    benzonitrile 72.55
    trioctyl phosphate 22.16
    1-bromopropane 34.87
    gamma-valerolactone 288.87
    n-decanol 22.14
    triethyl phosphate 38.58
    4-methyl-2-pentanol 37.79
    propionitrile 94.37
    vinylene carbonate 117.18
    1,1,2-trichlorotrifluoroethane 283.54
    DMS 86.79
    cumene 17.38
    2-octanol 15.58
    2-hexanone 74.9
    octyl acetate 32.68
    limonene 18.41
    1,2-dimethoxyethane 320.42
    ethyl orthosilicate 33.59
    tributyl phosphate 33.12
    diacetone alcohol 152.62
    N,N-dimethylaniline 69.55
    acrylonitrile 139.63
    aniline 53.21
    1,3-propanediol 215.62
    bromobenzene 29.12
    dibromomethane 77.75
    1,1,2,2-tetrachloroethane 233.71
    2-methyl-cyclohexyl acetate 51.2
    tetrabutyl urea 48.49
    diisobutyl methanol 21.9
    2-phenylethanol 62.83
    styrene 20.45
    dioctyl adipate 50.2
    dimethyl sulfate 178.95
    ethyl butyrate 45.57
    methyl lactate 124.11
    butyl lactate 45.69
    diethyl carbonate 42.98
    propanediol butyl ether 117.78
    triethyl orthoformate 41.41
    p-tert-butyltoluene 14.36
    methyl 4-tert-butylbenzoate 80.16
    morpholine 322.22
    tert-butylamine 71.53
    n-dodecanol 17.31
    dimethoxymethane 243.76
    ethylene carbonate 88.19
    cyrene 132.55
    2-ethoxyethyl acetate 60.69
    2-ethylhexyl acetate 39.4
    1,2,4-trichlorobenzene 70.92
    4-methylpyridine 100.61
    dibutyl ether 31.53
    2,6-dimethyl-4-heptanol 21.9
    DEF 139.79
    dimethyl isosorbide 192.53
    tetrachloroethylene 99.33
    eugenol 89.08
    triacetin 99.85
    span 80 91.57
    1,4-butanediol 92.93
    1,1-dichloroethane 94.81
    2-methyl-1-pentanol 68.22
    methyl formate 179.42
    2-methyl-1-butanol 76.68
    n-decane 2.15
    butyronitrile 77.54
    3,7-dimethyl-1-octanol 37.67
    1-chlorooctane 13.57
    1-chlorotetradecane 6.4
    n-nonane 1.76
    undecane 1.76
    tert-butylcyclohexane 4.14
    cyclooctane 0.55
    cyclopentanol 87.94
    tetrahydropyran 112.71
    tert-amyl methyl ether 55.96
    2,5,8-trioxanonane 231.42
    1-hexene 13.84
    2-isopropoxyethanol 127.99
    2,2,2-trifluoroethanol 106.26
    methyl butyrate 82.88

    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