1-(2,3,6-Trimethylphenyl)-3-buten-2-one

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  • Identifiers

    CAS number
    54789-45-6

    Molecular formula
    C13H16O

    SMILES
    CC1=C(C(=C(C=C1)C)CC(=O)C=C)C

    Retention indicies (RI)

    • Carbowax: 2180.0

  • Odor profile

    Floral 62.21%
    Green 55.96%
    Sweet 36.19%
    Dry 29.07%
    Powdery 28.3%
    Neroli 28.27%
    Honey 28.19%
    Woody 26.6%
    Fatty 26.15%
    Fruity 25.74%

    Scent© AI

  • Properties

    XLogP3-AA
    3.2

    Molecular weight
    188.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    281°C

    Flash point est.
    115.82 ˚C

  • Synonyms

    • 54789-45-6
    • 1-(2,3,6-trimethylphenyl)but-3-en-2-one
    • 1-(2,3,6-TRIMETHYLPHENYL)-3-BUTEN-2-ONE
    • DTXSID90203260
    • DTXCID90125751
    • CHEBI:145959
    • DB-237443
    • 3-Buten-2-one 1-(2,3,6-trimethyl phenyl)

  • Applications

    1-(2,3,6-Trimethylphenyl)-3-buten-2-one (CAS 54789-45-6) is a reactive aromatic enone (Michael acceptor) used mainly as a versatile intermediate in synthesis and catalysis: a building block for 1,4-additions with thiols/amines/alcohols, selective hydrogenation, double-bond epoxidation, cyclizations to heterocycles (chromenes, benzofurans, pyridines), a dienophile in Diels-Alder reactions, and a model substrate for developing asymmetric conjugate additions, transition-metal-catalyzed transformations, and thiol–Michael surface/polymer modifications; it is also employed in medicinal and agrochemical research as a modified chalcone-like motif for SAR libraries, and as a precursor to multi-methylated aryl fragments in fine chemicals and materials where hydrophobicity and UV absorption of the aryl unit are tuned.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 155.38
    methanol 140.92
    isopropanol 130.71
    water 0.43
    ethyl acetate 350.93
    n-propanol 162.87
    acetone 266.4
    n-butanol 145.6
    acetonitrile 237.15
    DMF 474.71
    toluene 293.91
    isobutanol 115.6
    1,4-dioxane 777.84
    methyl acetate 372.36
    THF 666.41
    2-butanone 383.81
    n-pentanol 107.15
    sec-butanol 129.29
    n-hexane 40.93
    ethylene glycol 18.64
    NMP 280.75
    cyclohexane 68.05
    DMSO 162.34
    n-butyl acetate 272.06
    n-octanol 67.14
    chloroform 886.42
    n-propyl acetate 184.61
    acetic acid 77.72
    dichloromethane 822.49
    cyclohexanone 475.0
    propylene glycol 31.06
    isopropyl acetate 171.81
    DMAc 418.32
    2-ethoxyethanol 137.96
    isopentanol 122.88
    n-heptane 32.21
    ethyl formate 173.88
    1,2-dichloroethane 531.08
    n-hexanol 181.17
    2-methoxyethanol 206.14
    isobutyl acetate 129.49
    tetrachloromethane 139.05
    n-pentyl acetate 131.98
    transcutol 383.69
    n-heptanol 71.75
    ethylbenzene 202.92
    MIBK 147.18
    2-propoxyethanol 238.58
    tert-butanol 184.06
    MTBE 256.11
    2-butoxyethanol 123.81
    propionic acid 116.34
    o-xylene 192.95
    formic acid 23.06
    diethyl ether 364.32
    m-xylene 174.12
    p-xylene 239.27
    chlorobenzene 293.05
    dimethyl carbonate 115.43
    n-octane 17.71
    formamide 67.42
    cyclopentanone 490.5
    2-pentanone 260.11
    anisole 330.14
    cyclopentyl methyl ether 272.96
    gamma-butyrolactone 446.72
    1-methoxy-2-propanol 161.11
    pyridine 498.95
    3-pentanone 272.97
    furfural 341.54
    n-dodecane 12.29
    diethylene glycol 107.66
    diisopropyl ether 89.45
    tert-amyl alcohol 161.38
    acetylacetone 237.49
    n-hexadecane 14.44
    acetophenone 237.85
    methyl propionate 274.82
    isopentyl acetate 230.88
    trichloroethylene 805.25
    n-nonanol 68.72
    cyclohexanol 143.27
    benzyl alcohol 171.56
    2-ethylhexanol 122.73
    isooctanol 62.8
    dipropyl ether 184.32
    1,2-dichlorobenzene 247.61
    ethyl lactate 63.97
    propylene carbonate 223.98
    n-methylformamide 173.97
    2-pentanol 93.7
    n-pentane 28.3
    1-propoxy-2-propanol 169.14
    1-methoxy-2-propyl acetate 219.14
    2-(2-methoxypropoxy) propanol 136.26
    mesitylene 104.66
    ε-caprolactone 343.77
    p-cymene 91.49
    epichlorohydrin 607.41
    1,1,1-trichloroethane 459.68
    2-aminoethanol 54.56
    morpholine-4-carbaldehyde 383.87
    sulfolane 288.85
    2,2,4-trimethylpentane 18.78
    2-methyltetrahydrofuran 474.66
    n-hexyl acetate 180.68
    isooctane 14.37
    2-(2-butoxyethoxy)ethanol 156.97
    sec-butyl acetate 145.88
    tert-butyl acetate 172.52
    decalin 42.68
    glycerin 36.55
    diglyme 325.04
    acrylic acid 84.09
    isopropyl myristate 80.96
    n-butyric acid 152.07
    acetyl acetate 172.35
    di(2-ethylhexyl) phthalate 72.49
    ethyl propionate 190.51
    nitromethane 219.78
    1,2-diethoxyethane 268.59
    benzonitrile 201.61
    trioctyl phosphate 47.36
    1-bromopropane 331.63
    gamma-valerolactone 548.08
    n-decanol 53.54
    triethyl phosphate 93.4
    4-methyl-2-pentanol 66.29
    propionitrile 254.73
    vinylene carbonate 223.0
    1,1,2-trichlorotrifluoroethane 192.1
    DMS 177.27
    cumene 120.04
    2-octanol 54.81
    2-hexanone 204.37
    octyl acetate 97.67
    limonene 121.36
    1,2-dimethoxyethane 377.12
    ethyl orthosilicate 95.55
    tributyl phosphate 61.42
    diacetone alcohol 143.14
    N,N-dimethylaniline 206.38
    acrylonitrile 264.31
    aniline 222.67
    1,3-propanediol 85.21
    bromobenzene 320.61
    dibromomethane 550.98
    1,1,2,2-tetrachloroethane 602.06
    2-methyl-cyclohexyl acetate 169.03
    tetrabutyl urea 82.42
    diisobutyl methanol 69.08
    2-phenylethanol 194.39
    styrene 230.59
    dioctyl adipate 105.45
    dimethyl sulfate 139.74
    ethyl butyrate 198.43
    methyl lactate 72.24
    butyl lactate 76.23
    diethyl carbonate 137.03
    propanediol butyl ether 78.3
    triethyl orthoformate 131.58
    p-tert-butyltoluene 88.61
    methyl 4-tert-butylbenzoate 153.37
    morpholine 683.2
    tert-butylamine 127.43
    n-dodecanol 43.28
    dimethoxymethane 318.38
    ethylene carbonate 192.85
    cyrene 130.84
    2-ethoxyethyl acetate 199.47
    2-ethylhexyl acetate 199.94
    1,2,4-trichlorobenzene 268.53
    4-methylpyridine 487.9
    dibutyl ether 130.33
    2,6-dimethyl-4-heptanol 69.08
    DEF 287.06
    dimethyl isosorbide 275.65
    tetrachloroethylene 389.76
    eugenol 149.93
    triacetin 146.72
    span 80 100.62
    1,4-butanediol 38.41
    1,1-dichloroethane 505.65
    2-methyl-1-pentanol 115.82
    methyl formate 137.02
    2-methyl-1-butanol 114.94
    n-decane 20.85
    butyronitrile 218.47
    3,7-dimethyl-1-octanol 74.0
    1-chlorooctane 75.58
    1-chlorotetradecane 32.91
    n-nonane 19.5
    undecane 15.69
    tert-butylcyclohexane 41.34
    cyclooctane 22.02
    cyclopentanol 142.19
    tetrahydropyran 642.55
    tert-amyl methyl ether 188.72
    2,5,8-trioxanonane 224.36
    1-hexene 146.48
    2-isopropoxyethanol 119.79
    2,2,2-trifluoroethanol 43.28
    methyl butyrate 223.48

    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
Averrhoa bilimbi fruit (Malaysia) Averrhoa bilimbi L., fam. Oxalidaceae 0.4%
Tamarind 3 fruit Tamarindus indica L., fam. Leguminosae 0.3%