Methyl 4-chloroacetoacetate

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  • Identifiers

    CAS number
    32807-28-6

    Molecular formula
    C5H7ClO3

    SMILES
    COC(=O)CC(=O)CCl

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Fruity 60.37%
    Caramellic 54.98%
    Sweet 37.4%
    Buttery 36.86%
    Winey 36.76%
    Burnt 32.19%
    Fatty 30.34%
    Nutty 27.5%
    Creamy 27.35%
    Ethereal 27.28%

     

    Flavor
    Fruity 56.82%
    Odorless 25.94%
    Cheese 25.4%
    Cooked 24.44%
    Roquefort cheese 20.8%
    Nutty 20.75%
    Marshmallow 20.7%
    Creamy 20.67%
    Stinky 20.62%
    Mild 20.59%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    7.13 (neutral)

    Molecular weight
    150.56 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    215°C

    Flash point

    • 90.83 ˚C est.

  • Synonyms

    • Methyl 4-chloroacetoacetate
    • Methyl 4-chloro-3-oxobutyrate
    • Butanoic acid, 4-chloro-3-oxo-, methyl ester
    • 4-chloro-3-oxobutanoic acid methyl ester
    • FVC6V863Y2
    • DTXSID0067719
    • Methyl .omega.-chloroacetoacetate
    • .gamma.-Chloroacetoacetic acid, methyl ester
    • RefChem:157604
    • Methyl omega-chloroacetoacetate
    • DTXCID7038579
    • gamma-Chloroacetoacetic acid, methyl ester
    • HFLMYYLFSNEOOT-UHFFFAOYSA-N
    • 32807-28-6
    • Methyl 4-chloro-3-oxobutanoate
    • methyl 4-chloro-3-oxo-butanoate
    • 4-Chloroacetoacetic Acid Methyl Ester
    • MFCD00000938
    • methyl-4-chloroacetoacetate
    • ACETOACETIC ACID, 4-CHLORO-, METHYL ESTER
    • 4-Chloro-3-oxo-butyric acid methyl ester
    • Methyl gamma-chloroacetoacetate
    • EINECS 251-230-5
    • BRN 1759939
    • methyl chloroacetoacetate
    • methyl 4-chloro-acetoacetate
    • UNII-FVC6V863Y2
    • SCHEMBL56154
    • 3-03-00-01207 (Beilstein Handbook Reference)
    • methyl-gamma-chloroacetoacetate
    • Methyl4-chloro-3-oxobutanoate
    • CHEMBL173804
    • methyl 4-chloro-3-oxo-butyrate
    • 4-chloro-acetoaceticacimethylester
    • Methyl .gamma.-chloroacetoacetate
    • Methyl 4-chloro-3-oxobutanoate #
    • Methyl 4-chloroacetoacetate, 97%
    • BB_SC-11229
    • STR04472
    • BBL027316
    • SBB061676
    • STL185651
    • AKOS000119618
    • FM25435
    • 4-chloro aceto acetic acid methyl ester
    • 4-chloro-3-oxobutanoic acid, methyl ester
    • 4-chloro-3-oxobutanoic acid. methyl ester
    • DB-048271
    • CS-0044248
    • methyl 4-chloranyl-3-oxidanylidene-butanoate
    • NS00029354
    • ST51047669
    • EN300-19679
    • 07M286
    • S12341
    • A821427
    • F013919
    • F0001-0971
    • 32807-28-6

  • Applications

    Methyl 4-chloroacetoacetate is a versatile beta-keto ester that serves as an intermediate and building block in organic synthesis. In medicinal chemistry, it is commonly evaluated for the preparation of heterocycles and related pharmacophores, enabling routes to pyrazoles, pyrimidines, and other bioactive cores. In the agrochemical sector, it may be used as a precursor to intermediates for herbicides and fungicides. It also finds use in general organic synthesis as an electrophilic substrate for SN2 substitutions at the 4-chloro position and for Knoevenagel-type condensations and Michael-type additions to access beta-dicarbonyl derived products. Additionally, it may be employed in polymer or materials chemistry as a functionalized building block for specialty monomers or crosslinkable esters, subject to formulation needs. Finally, it is typically handled as an intermediate under standard chemical regulations, with use limited by local guidelines.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 295.64
    methanol 539.71
    isopropanol 270.94
    water 230.21
    ethyl acetate 206.29
    n-propanol 174.92
    acetone 794.54
    n-butanol 139.56
    acetonitrile 532.86
    DMF 2022.66
    toluene 53.5
    isobutanol 145.2
    1,4-dioxane 479.97
    methyl acetate 364.96
    THF 487.63
    2-butanone 321.83
    n-pentanol 87.85
    sec-butanol 181.02
    n-hexane 14.72
    ethylene glycol 271.69
    NMP 1333.25
    cyclohexane 20.59
    DMSO 1370.66
    n-butyl acetate 55.73
    n-octanol 52.03
    chloroform 382.69
    n-propyl acetate 97.78
    acetic acid 492.54
    dichloromethane 417.93
    cyclohexanone 304.08
    propylene glycol 203.74
    isopropyl acetate 107.56
    DMAc 1997.7
    2-ethoxyethanol 313.09
    isopentanol 118.12
    n-heptane 9.27
    ethyl formate 242.45
    1,2-dichloroethane 274.05
    n-hexanol 53.34
    2-methoxyethanol 661.17
    isobutyl acetate 58.07
    tetrachloromethane 69.51
    n-pentyl acetate 44.26
    transcutol 387.17
    n-heptanol 31.45
    ethylbenzene 42.41
    MIBK 109.08
    2-propoxyethanol 171.77
    tert-butanol 341.77
    MTBE 181.78
    2-butoxyethanol 93.24
    propionic acid 222.55
    o-xylene 70.7
    formic acid 447.13
    diethyl ether 155.12
    m-xylene 51.69
    p-xylene 67.15
    chlorobenzene 88.19
    dimethyl carbonate 187.91
    n-octane 4.81
    formamide 697.81
    cyclopentanone 429.29
    2-pentanone 188.81
    anisole 164.2
    cyclopentyl methyl ether 178.09
    gamma-butyrolactone 492.52
    1-methoxy-2-propanol 411.37
    pyridine 253.07
    3-pentanone 175.57
    furfural 555.21
    n-dodecane 5.84
    diethylene glycol 255.33
    diisopropyl ether 38.14
    tert-amyl alcohol 228.97
    acetylacetone 296.08
    n-hexadecane 6.48
    acetophenone 172.89
    methyl propionate 242.52
    isopentyl acetate 55.95
    trichloroethylene 467.63
    n-nonanol 46.53
    cyclohexanol 150.12
    benzyl alcohol 133.54
    2-ethylhexanol 40.08
    isooctanol 30.04
    dipropyl ether 54.77
    1,2-dichlorobenzene 107.93
    ethyl lactate 99.69
    propylene carbonate 229.4
    n-methylformamide 706.72
    2-pentanol 90.16
    n-pentane 14.55
    1-propoxy-2-propanol 109.99
    1-methoxy-2-propyl acetate 97.99
    2-(2-methoxypropoxy) propanol 161.62
    mesitylene 37.5
    ε-caprolactone 226.13
    p-cymene 29.59
    epichlorohydrin 449.99
    1,1,1-trichloroethane 239.55
    2-aminoethanol 273.78
    morpholine-4-carbaldehyde 890.54
    sulfolane 647.92
    2,2,4-trimethylpentane 9.87
    2-methyltetrahydrofuran 292.65
    n-hexyl acetate 75.91
    isooctane 6.15
    2-(2-butoxyethoxy)ethanol 159.18
    sec-butyl acetate 65.18
    tert-butyl acetate 113.42
    decalin 13.79
    glycerin 361.84
    diglyme 353.76
    acrylic acid 262.91
    isopropyl myristate 37.73
    n-butyric acid 171.47
    acetyl acetate 162.34
    di(2-ethylhexyl) phthalate 46.93
    ethyl propionate 119.18
    nitromethane 1160.83
    1,2-diethoxyethane 103.17
    benzonitrile 148.45
    trioctyl phosphate 32.21
    1-bromopropane 114.93
    gamma-valerolactone 570.11
    n-decanol 36.52
    triethyl phosphate 60.98
    4-methyl-2-pentanol 54.34
    propionitrile 209.56
    vinylene carbonate 236.22
    1,1,2-trichlorotrifluoroethane 491.92
    DMS 107.51
    cumene 37.65
    2-octanol 25.71
    2-hexanone 110.2
    octyl acetate 48.79
    limonene 43.63
    1,2-dimethoxyethane 603.02
    ethyl orthosilicate 54.72
    tributyl phosphate 40.3
    diacetone alcohol 195.46
    N,N-dimethylaniline 167.14
    acrylonitrile 327.6
    aniline 143.23
    1,3-propanediol 282.97
    bromobenzene 74.79
    dibromomethane 231.06
    1,1,2,2-tetrachloroethane 389.05
    2-methyl-cyclohexyl acetate 63.81
    tetrabutyl urea 76.78
    diisobutyl methanol 30.28
    2-phenylethanol 73.51
    styrene 56.61
    dioctyl adipate 69.4
    dimethyl sulfate 429.74
    ethyl butyrate 68.58
    methyl lactate 222.23
    butyl lactate 55.53
    diethyl carbonate 63.74
    propanediol butyl ether 109.98
    triethyl orthoformate 60.84
    p-tert-butyltoluene 29.2
    methyl 4-tert-butylbenzoate 123.01
    morpholine 513.55
    tert-butylamine 176.92
    n-dodecanol 30.22
    dimethoxymethane 576.02
    ethylene carbonate 173.25
    cyrene 214.17
    2-ethoxyethyl acetate 77.32
    2-ethylhexyl acetate 43.8
    1,2,4-trichlorobenzene 139.43
    4-methylpyridine 287.36
    dibutyl ether 53.52
    2,6-dimethyl-4-heptanol 30.28
    DEF 425.12
    dimethyl isosorbide 219.22
    tetrachloroethylene 250.16
    eugenol 126.28
    triacetin 128.19
    span 80 98.76
    1,4-butanediol 125.41
    1,1-dichloroethane 264.04
    2-methyl-1-pentanol 84.36
    methyl formate 574.66
    2-methyl-1-butanol 120.86
    n-decane 8.54
    butyronitrile 169.34
    3,7-dimethyl-1-octanol 52.33
    1-chlorooctane 31.1
    1-chlorotetradecane 16.23
    n-nonane 7.97
    undecane 6.79
    tert-butylcyclohexane 13.11
    cyclooctane 7.25
    cyclopentanol 201.0
    tetrahydropyran 233.13
    tert-amyl methyl ether 136.74
    2,5,8-trioxanonane 273.1
    1-hexene 42.62
    2-isopropoxyethanol 173.43
    2,2,2-trifluoroethanol 339.77
    methyl butyrate 163.1

    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