4-Penten-2-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    13891-87-7

    Molecular formula
    C5H8O

    SMILES
    CC(=O)CC=C

  • Odor profile

    Pungent 68.13%
    Fruity 61.63%
    Green 60.94%
    Ethereal 53.37%
    Sharp 43.93%
    Spicy 42.31%
    Alliaceous 41.7%
    Gassy 36.83%
    Radish 36.82%
    Metallic 36.58%

    Scent© AI

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    7.8 (neutral)

    Molecular weight
    84.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    104°C

    Flash point est.
    7.79 ˚C

  • Synonyms

    • 4-Penten-2-one
    • pent-4-en-2-one
    • 13891-87-7
    • Allyl methyl ketone
    • Vinyl acetone
    • 4CUM84CQ9J
    • vinylacetone
    • Methyl allyl ketone
    • 1-Penten-4-one
    • UNII-4CUM84CQ9J
    • CH3C(O)CH2CH=CH2
    • CHEBI:87508
    • PNJWIWWMYCMZRO-UHFFFAOYSA-
    • DTXSID50160840
    • LMFA12000034
    • AKOS005138063
    • DB-361504
    • EN300-126905
    • Q27159683
    • InChI=1/C5H8O/c1-3-4-5(2)6/h3H,1,4H2,2H3

  • Applications

    4-Penten-2-one (CAS 13891-87-7) is a terminal-alkene ketone that serves as a highly versatile bifunctional building block: it is used as an intermediate to access alcohols and diols via hydroboration–oxidation and epoxide opening, to form epoxides or thioethers through epoxidation/thiol–ene chemistry, to generate acetoacetaldehyde by ozonolysis, to create conjugated enones by olefin metathesis (notably cross-metathesis with acrylates and other alkenes), and to introduce new functionality by hydrosilylation or hydroformylation; it also enables ketone tagging onto materials and polymers (radical grafting, thiol–ene, hydrosilylation) for post-functionalization (oxime/hydrazone formation), serves as a precursor in the synthesis of pharmaceuticals, agrochemicals, fragrance/flavor ingredients, and surfactants, and is employed as a probe/analytical standard to study chemoselective hydrogenation of C=C vs C=O, for catalyst screening, and for flow-process development owing to the orthogonal reactivity of its two functional groups.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 772.76
    methanol 1063.01
    isopropanol 556.32
    water 57.05
    ethyl acetate 350.84
    n-propanol 547.94
    acetone 494.71
    n-butanol 484.17
    acetonitrile 431.44
    DMF 661.01
    toluene 106.94
    isobutanol 376.52
    1,4-dioxane 577.85
    methyl acetate 359.93
    THF 707.96
    2-butanone 383.16
    n-pentanol 336.88
    sec-butanol 451.51
    n-hexane 179.22
    ethylene glycol 323.76
    NMP 658.66
    cyclohexane 133.89
    DMSO 384.78
    n-butyl acetate 218.67
    n-octanol 265.45
    chloroform 514.42
    n-propyl acetate 171.41
    acetic acid 889.6
    dichloromethane 383.12
    cyclohexanone 438.85
    propylene glycol 324.11
    isopropyl acetate 185.84
    DMAc 579.02
    2-ethoxyethanol 418.7
    isopentanol 328.77
    n-heptane 108.36
    ethyl formate 223.98
    1,2-dichloroethane 219.68
    n-hexanol 474.83
    2-methoxyethanol 675.15
    isobutyl acetate 116.16
    tetrachloromethane 126.01
    n-pentyl acetate 157.98
    transcutol 1275.91
    n-heptanol 177.56
    ethylbenzene 79.8
    MIBK 177.24
    2-propoxyethanol 554.48
    tert-butanol 590.48
    MTBE 360.95
    2-butoxyethanol 253.47
    propionic acid 501.21
    o-xylene 110.72
    formic acid 412.01
    diethyl ether 409.32
    m-xylene 99.7
    p-xylene 106.01
    chlorobenzene 137.73
    dimethyl carbonate 106.96
    n-octane 38.08
    formamide 281.7
    cyclopentanone 454.59
    2-pentanone 306.23
    anisole 183.81
    cyclopentyl methyl ether 373.14
    gamma-butyrolactone 496.18
    1-methoxy-2-propanol 482.98
    pyridine 264.98
    3-pentanone 244.43
    furfural 383.77
    n-dodecane 32.83
    diethylene glycol 477.34
    diisopropyl ether 128.53
    tert-amyl alcohol 459.05
    acetylacetone 285.79
    n-hexadecane 34.93
    acetophenone 159.01
    methyl propionate 282.5
    isopentyl acetate 184.28
    trichloroethylene 351.2
    n-nonanol 220.07
    cyclohexanol 414.6
    benzyl alcohol 170.12
    2-ethylhexanol 236.53
    isooctanol 131.2
    dipropyl ether 226.24
    1,2-dichlorobenzene 131.54
    ethyl lactate 122.2
    propylene carbonate 251.97
    n-methylformamide 353.0
    2-pentanol 337.69
    n-pentane 148.69
    1-propoxy-2-propanol 392.45
    1-methoxy-2-propyl acetate 233.38
    2-(2-methoxypropoxy) propanol 299.14
    mesitylene 71.74
    ε-caprolactone 387.19
    p-cymene 74.62
    epichlorohydrin 367.68
    1,1,1-trichloroethane 263.33
    2-aminoethanol 433.1
    morpholine-4-carbaldehyde 618.79
    sulfolane 452.43
    2,2,4-trimethylpentane 63.13
    2-methyltetrahydrofuran 558.71
    n-hexyl acetate 316.47
    isooctane 39.79
    2-(2-butoxyethoxy)ethanol 412.89
    sec-butyl acetate 119.14
    tert-butyl acetate 195.31
    decalin 60.11
    glycerin 410.48
    diglyme 545.2
    acrylic acid 408.62
    isopropyl myristate 123.48
    n-butyric acid 459.63
    acetyl acetate 199.48
    di(2-ethylhexyl) phthalate 117.96
    ethyl propionate 160.75
    nitromethane 692.07
    1,2-diethoxyethane 328.34
    benzonitrile 177.43
    trioctyl phosphate 86.47
    1-bromopropane 203.01
    gamma-valerolactone 560.64
    n-decanol 160.13
    triethyl phosphate 80.99
    4-methyl-2-pentanol 165.0
    propionitrile 297.5
    vinylene carbonate 222.84
    1,1,2-trichlorotrifluoroethane 350.92
    DMS 198.19
    cumene 71.09
    2-octanol 137.45
    2-hexanone 226.93
    octyl acetate 164.17
    limonene 138.93
    1,2-dimethoxyethane 495.8
    ethyl orthosilicate 86.33
    tributyl phosphate 109.05
    diacetone alcohol 272.78
    N,N-dimethylaniline 138.35
    acrylonitrile 285.43
    aniline 190.16
    1,3-propanediol 458.34
    bromobenzene 113.15
    dibromomethane 278.46
    1,1,2,2-tetrachloroethane 294.36
    2-methyl-cyclohexyl acetate 148.72
    tetrabutyl urea 145.07
    diisobutyl methanol 112.43
    2-phenylethanol 192.76
    styrene 92.21
    dioctyl adipate 159.01
    dimethyl sulfate 149.08
    ethyl butyrate 145.94
    methyl lactate 188.91
    butyl lactate 142.34
    diethyl carbonate 96.16
    propanediol butyl ether 308.33
    triethyl orthoformate 117.05
    p-tert-butyltoluene 76.16
    methyl 4-tert-butylbenzoate 176.68
    morpholine 646.4
    tert-butylamine 390.33
    n-dodecanol 120.97
    dimethoxymethane 352.3
    ethylene carbonate 190.17
    cyrene 213.09
    2-ethoxyethyl acetate 211.12
    2-ethylhexyl acetate 149.93
    1,2,4-trichlorobenzene 167.39
    4-methylpyridine 283.16
    dibutyl ether 235.01
    2,6-dimethyl-4-heptanol 112.43
    DEF 361.07
    dimethyl isosorbide 357.42
    tetrachloroethylene 226.76
    eugenol 177.58
    triacetin 257.98
    span 80 296.04
    1,4-butanediol 224.7
    1,1-dichloroethane 281.74
    2-methyl-1-pentanol 262.56
    methyl formate 255.26
    2-methyl-1-butanol 347.63
    n-decane 55.64
    butyronitrile 295.7
    3,7-dimethyl-1-octanol 226.85
    1-chlorooctane 147.06
    1-chlorotetradecane 62.5
    n-nonane 58.92
    undecane 41.12
    tert-butylcyclohexane 67.11
    cyclooctane 48.88
    cyclopentanol 423.96
    tetrahydropyran 530.27
    tert-amyl methyl ether 296.58
    2,5,8-trioxanonane 414.84
    1-hexene 274.53
    2-isopropoxyethanol 285.91
    2,2,2-trifluoroethanol 272.17
    methyl butyrate 197.2

    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

Botanical

Name CAS Botanical Proportion
Tamarind 1 dried fruit Tamarindus indica L., fam. Leguminosae 0.05%