Ethyl acetoacetate

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  • Identifiers

    CAS number
    141-97-9

    Molecular formula
    C6H10O3

    SMILES
    CCOC(=O)CC(=O)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 94.21%
    Green 76.27%
    Apple 68.37%
    Winey 59.87%
    Sweet 57.92%
    Caramellic 50.19%
    Ethereal 50.07%
    Rummy 44.59%
    Fresh 41.79%
    Pineapple 41.65%

     

    Flavor
    Fruity 88.75%
    Green 67.01%
    Apple 48.53%
    Sweet 45.0%
    Fresh 42.19%
    Fatty 38.56%
    Tropical 36.58%
    Pineapple 36.19%
    Sharp 34.36%
    Fruit 32.67%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    8.02 (weak base)

    Molecular weight
    130.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Melting point expt.

    • less than -112 °F (USCG, 1999)
    • -45 °C

    Boiling point

    • 363 °F at 760 mmHg (USCG, 1999)
    • 180.8 °C AT 760 MM HG
    • 180.00 to 181.00 °C. @ 760.00 mm Hg
    • 180.8 °C

    Flash point

    • 63.03 ˚C est.
    • 135 °F (USCG, 1999)
    • 184 °F CC (84.4 °C)
    • 70 °C c.c.

    Solubility expt.

    • SOL IN ABOUT 35 PARTS WATER
    • SOL IN BENZENE, & CHLOROFORM; MISCIBLE WITH ETHER, & ACETONE
    • water solubility = 1.11X10+5 mg/l @ 17 °C
    • 110 mg/mL at 17 °C
    • Solubility in water, g/100ml at 20 °C: 2.86
    • miscible in alcohol, ether, ethyl acetate, 1 ml in 12 ml water

  • Synonyms

    • ethyl acetoacetate
    • ethyl 3-oxobutanoate
    • 141-97-9
    • ethyl acetylacetate
    • diacetic ether
    • ethyl 3-oxobutyrate
    • Butanoic acid, 3-oxo-, ethyl ester
    • Acetoacetic ester
    • acetoacetic acid, ethyl ester
    • ethyl acetylacetonate
    • 3-oxobutanoic acid ethyl ester
    • Active acetylacetate
    • Ethyl acetyl acetate
    • active acetyl acetate
    • ethyl beta-ketobutyrate
    • Ethylacetacetat
    • ACETOACETIC ACID ETHYL ESTER
    • ethyl-acetoacetate
    • Acetoctan ethylnaty
    • 3-Oxo-butyric acid ethyl ester
    • 1-Ethoxybutane-1,3-dione
    • ETHYLACETOACETATE
    • 3-Oxobutyric Acid Ethyl Ester
    • FEMA No. 2415
    • NSC 8657
    • Ethylester kyseliny acetoctove
    • CCRIS 1343
    • HSDB 402
    • UNII-IZP61H3TB1
    • EAA
    • EINECS 205-516-1
    • IZP61H3TB1
    • ethyl-3-oxobutanoate
    • CHEBI:4893
    • DTXSID2027092
    • AI3-00066
    • butanoic acid, 3-oxo-ethyl ester
    • NSC-8657
    • ETHYL 3-OXYBUTANOATE
    • DTXCID207092
    • ethyl 2-methyl-3-oxopropionate
    • NSC-657
    • EC 205-516-1
    • NSC-37390
    • ETHYL ACETOACETATE (3,4-13C2)
    • Ethylacetacetat [Czech]
    • Acetoctan ethylnaty [Czech]
    • ETHYL ACETOACETATE (2,4-13C2)
    • MFCD00009199
    • Acetoacetic acid ethylester
    • Ethyl acetoacetate (EAA)
    • Ethylester kyseliny acetoctove [Czech]
    • ethylacetoaceate
    • ethyl acetoaceate
    • ethyl acetoacetat
    • ethyl acetoactate
    • etyl acetoacetate
    • EAC
    • Ethyl-3-oxobutyrate
    • ethyl 3-ketobutyrate
    • ethyl 3-oxo-butyrate
    • DIACETIC ESTER
    • ethyl 3-oxo-butanoate
    • ethyl-3-oxo-butanoate
    • acetoacetate ethyl ester
    • ethyl alpha-acetoacetate
    • ethyl 3-keto-n-butanoate
    • Ethyl acetoacetate, 99%
    • bmse000944
    • Ethyl acetoacetate, natural
    • SCHEMBL15500
    • Ethyl 3-hydroxy-2-butenoate
    • Ethyl acetoacetate, >=99%
    • ethyl 3-oxidanylidenebutanoate
    • Ethyl acetoacetate (Standard)
    • WLN: 2OV1V1
    • ETHYL ACETONECARBOXYLATE
    • 3-ketobutyric acid ethyl ester
    • CHEMBL169176
    • ETHYL ACETOACETATE [MI]
    • 3-oxo-butanoic acid ethyl ester
    • ETHYL ACETOACETATE [FCC]
    • FEMA 2415
    • HY-Y1093R
    • ETHYL ACETOACETATE [FHFI]
    • ETHYL ACETOACETATE [HSDB]
    • NSC8657
    • BCP29449
    • HY-Y1093
    • STR00044
    • Tox21_200645
    • BBL012204
    • ETHYL ACETOACETATE (3-13C)
    • s6024
    • STL163546
    • AKOS000118955
    • Ethyl acetoacetate, >=98.0% (GC)
    • Ethyl acetoacetate, analytical standard
    • FE12158
    • Ethyl acetoacetate, >=99%, FCC, FG
    • NCGC00248778-01
    • NCGC00258199-01
    • CAS-141-97-9
    • ETHYL ACETOACETATE (1,3-13C2)
    • Ethyl acetoacetate, natural, >=97%, FG
    • Ethyl acetoacetate, ReagentPlus(R), 99%
    • A0649
    • CS-0016216
    • NS00008361
    • EN300-19204
    • C03500
    • G75780
    • Q47192
    • Ethyl acetoacetate, Vetec(TM) reagent grade, 98%
    • Ethyl acetoacetate, Lonza quality, >=99.0% (GC)
    • Ethyl acetoacetate, puriss. p.a., >=99.0% (GC)
    • F1908-0178
    • Z104473158
    • InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H
    • 205-516-1

  • Applications

    Ethyl acetoacetate (EAA, CAS 141-97-9) is a versatile, fruity-smelling liquid that serves as a key acetoacetylating agent in organic synthesis, enabling the manufacture of pharmaceuticals (e.g., antipyrine, vitamins, semisynthetic cephalosporins), agrochemicals, azo couplers, pigments and dyes, alkyd resins, plasticizers, adhesives and weather-resistant coatings; it also functions as a reaction solvent in acylations, a flavor ingredient imparting apple, peach and pineapple notes in food and beverages, an intermediate for surfactants, UV stabilizers for polymers, metal chelating ligands in catalytic systems, as well as an additive that improves fuel smoothness and an important raw material for ink production.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 420.53
    methanol 739.42
    isopropanol 342.41
    water 91.1
    ethyl acetate 245.4
    n-propanol 266.79
    acetone 582.1
    n-butanol 221.41
    acetonitrile 462.01
    DMF 1077.84
    toluene 63.06
    isobutanol 191.97
    1,4-dioxane 588.76
    methyl acetate 312.93
    THF 687.69
    2-butanone 225.61
    n-pentanol 136.29
    sec-butanol 220.72
    n-hexane 22.33
    ethylene glycol 319.24
    NMP 1007.82
    cyclohexane 38.38
    DMSO 599.73
    n-butyl acetate 70.03
    n-octanol 98.85
    chloroform 387.81
    n-propyl acetate 101.98
    acetic acid 875.08
    dichloromethane 367.38
    cyclohexanone 333.37
    propylene glycol 333.32
    isopropyl acetate 124.65
    DMAc 966.35
    2-ethoxyethanol 289.51
    isopentanol 157.83
    n-heptane 13.24
    ethyl formate 261.22
    1,2-dichloroethane 186.7
    n-hexanol 116.36
    2-methoxyethanol 707.55
    isobutyl acetate 60.86
    tetrachloromethane 47.02
    n-pentyl acetate 63.11
    transcutol 554.48
    n-heptanol 50.32
    ethylbenzene 47.01
    MIBK 111.32
    2-propoxyethanol 279.51
    tert-butanol 393.95
    MTBE 146.99
    2-butoxyethanol 110.44
    propionic acid 390.28
    o-xylene 73.61
    formic acid 423.7
    diethyl ether 164.89
    m-xylene 62.02
    p-xylene 64.1
    chlorobenzene 103.9
    dimethyl carbonate 172.46
    n-octane 6.93
    formamide 447.21
    cyclopentanone 428.62
    2-pentanone 184.9
    anisole 154.11
    cyclopentyl methyl ether 221.85
    gamma-butyrolactone 655.74
    1-methoxy-2-propanol 478.24
    pyridine 218.51
    3-pentanone 141.08
    furfural 594.64
    n-dodecane 10.14
    diethylene glycol 338.78
    diisopropyl ether 43.28
    tert-amyl alcohol 246.46
    acetylacetone 302.39
    n-hexadecane 11.05
    acetophenone 149.86
    methyl propionate 253.29
    isopentyl acetate 63.1
    trichloroethylene 344.44
    n-nonanol 83.53
    cyclohexanol 244.86
    benzyl alcohol 146.11
    2-ethylhexanol 61.29
    isooctanol 41.39
    dipropyl ether 68.23
    1,2-dichlorobenzene 122.75
    ethyl lactate 126.52
    propylene carbonate 339.88
    n-methylformamide 517.23
    2-pentanol 134.9
    n-pentane 21.7
    1-propoxy-2-propanol 160.02
    1-methoxy-2-propyl acetate 138.49
    2-(2-methoxypropoxy) propanol 211.41
    mesitylene 44.26
    ε-caprolactone 315.65
    p-cymene 34.76
    epichlorohydrin 437.77
    1,1,1-trichloroethane 191.84
    2-aminoethanol 354.44
    morpholine-4-carbaldehyde 833.7
    sulfolane 629.49
    2,2,4-trimethylpentane 13.26
    2-methyltetrahydrofuran 324.99
    n-hexyl acetate 138.13
    isooctane 8.94
    2-(2-butoxyethoxy)ethanol 249.26
    sec-butyl acetate 68.39
    tert-butyl acetate 132.96
    decalin 20.22
    glycerin 475.76
    diglyme 365.25
    acrylic acid 399.05
    isopropyl myristate 63.82
    n-butyric acid 339.05
    acetyl acetate 215.18
    di(2-ethylhexyl) phthalate 80.94
    ethyl propionate 134.93
    nitromethane 1070.02
    1,2-diethoxyethane 116.5
    benzonitrile 171.24
    trioctyl phosphate 55.03
    1-bromopropane 91.52
    gamma-valerolactone 684.59
    n-decanol 64.01
    triethyl phosphate 61.45
    4-methyl-2-pentanol 72.4
    propionitrile 226.29
    vinylene carbonate 353.26
    1,1,2-trichlorotrifluoroethane 428.47
    DMS 162.16
    cumene 41.15
    2-octanol 44.3
    2-hexanone 101.09
    octyl acetate 88.42
    limonene 49.92
    1,2-dimethoxyethane 469.57
    ethyl orthosilicate 55.42
    tributyl phosphate 67.91
    diacetone alcohol 228.48
    N,N-dimethylaniline 131.69
    acrylonitrile 336.41
    aniline 140.64
    1,3-propanediol 384.94
    bromobenzene 84.27
    dibromomethane 193.21
    1,1,2,2-tetrachloroethane 294.83
    2-methyl-cyclohexyl acetate 78.73
    tetrabutyl urea 103.56
    diisobutyl methanol 40.79
    2-phenylethanol 104.42
    styrene 59.42
    dioctyl adipate 115.44
    dimethyl sulfate 265.95
    ethyl butyrate 87.72
    methyl lactate 248.52
    butyl lactate 85.03
    diethyl carbonate 83.34
    propanediol butyl ether 184.99
    triethyl orthoformate 68.62
    p-tert-butyltoluene 34.99
    methyl 4-tert-butylbenzoate 155.8
    morpholine 575.4
    tert-butylamine 192.6
    n-dodecanol 51.98
    dimethoxymethane 469.78
    ethylene carbonate 262.0
    cyrene 232.91
    2-ethoxyethyl acetate 102.75
    2-ethylhexyl acetate 47.34
    1,2,4-trichlorobenzene 149.17
    4-methylpyridine 257.98
    dibutyl ether 77.3
    2,6-dimethyl-4-heptanol 40.79
    DEF 325.96
    dimethyl isosorbide 300.46
    tetrachloroethylene 181.59
    eugenol 159.24
    triacetin 197.77
    span 80 184.42
    1,4-butanediol 159.34
    1,1-dichloroethane 198.73
    2-methyl-1-pentanol 109.43
    methyl formate 474.63
    2-methyl-1-butanol 156.26
    n-decane 14.38
    butyronitrile 194.12
    3,7-dimethyl-1-octanol 85.47
    1-chlorooctane 48.21
    1-chlorotetradecane 25.54
    n-nonane 13.62
    undecane 11.8
    tert-butylcyclohexane 19.23
    cyclooctane 11.06
    cyclopentanol 289.13
    tetrahydropyran 317.74
    tert-amyl methyl ether 120.89
    2,5,8-trioxanonane 334.29
    1-hexene 56.53
    2-isopropoxyethanol 173.5
    2,2,2-trifluoroethanol 316.94
    methyl butyrate 170.77

    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