S-sec-Butyl 3-methylbut-2-enethioate

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    34322-09-3

    Molecular formula
    C9H16OS

    SMILES
    CCC(C)SC(=O)C=C(C)C

  • Odor profile

    Green 83.45%
    Sulfurous 82.26%
    Tropical 76.92%
    Fruity 76.05%
    Herbal 64.84%
    Vegetable 59.01%
    Spicy 49.61%
    Black currant 46.7%
    Grapefruit 44.87%
    Onion 41.59%

    Scent© AI

  • Properties

    XLogP3-AA
    3.4

    Molecular weight
    172.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    223°C

    Flash point est.
    83.21 ˚C

  • Synonyms

    • S-sec-Butyl 3-methylbut-2-enethioate
    • 34322-09-3
    • S-sec-Butyl 3-methyl-2-butenethioate
    • S-butan-2-yl 3-methylbut-2-enethioate
    • sec-Butyl S-senecthioate
    • AJD6235QYA
    • 2-Butenethioic acid, 3-methyl-, S-(1-methylpropyl) ester
    • 3-Methylthiocrotonic acid, S-sec-butyl ester
    • sec-Butyl 3-methyl-2-butenethioate
    • EINECS 251-938-4
    • sec-Butyl-3-methylbut-2-ene thioate
    • S-(1-Methylpropyl) 3-methylbut-2-enethioate
    • DTXSID60865713
    • UNII-AJD6235QYA
    • S-2-BUTYL 3-METHYLBUT-2-ENETHIOATE
    • SCHEMBL3504673
    • DTXCID00814088
    • GGGWOXLORXHXFZ-UHFFFAOYSA-N
    • S-s-butyl 3-methylbut-2-enethioate
    • AKOS006271519
    • sec-butyl-3-methyl but-2-ene thioate
    • NS00012048
    • Q27273956

  • Applications

    S-sec-Butyl 3-methylbut-2-enethioate (CAS 34322-09-3) is an aliphatic thioester valued as an activated acylating agent and versatile intermediate: it undergoes efficient transthioesterification and S→N/O acyl transfer to form amides and esters under mild conditions; serves as a precursor to ketones via thioester-based coupling and to aldehydes via Fukuyama-type reduction; and delivers the 3-methylbut-2-enoyl unit into pharmaceutical, agrochemical, and functional-material scaffolds; in fundamental studies it is used as a model substrate to probe acyl-transfer mechanisms/kinetics, esterase/thioesterase activity, and to mimic the reactivity of biological acyl‑CoA thioesters; in aroma chemistry, trace-level aliphatic thioesters can provide sulfur-driven lift (tropical fruit, wine, savory) or act as hydrolysis-triggered pro-odorants, making this compound suitable for fragrance/flavor R&D and odor libraries; it is also useful in dynamic covalent chemistry (assembly/polymer modification via transthioesterification) and as an analytical reference when developing GC/LC‑MS methods for hydrolysis-prone sulfur compounds.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1113.25
    methanol 894.79
    isopropanol 1204.9
    water 1.04
    ethyl acetate 670.73
    n-propanol 1047.18
    acetone 1104.45
    n-butanol 1116.15
    acetonitrile 823.82
    DMF 1371.19
    toluene 716.16
    isobutanol 890.12
    1,4-dioxane 1593.99
    methyl acetate 685.78
    THF 2558.86
    2-butanone 1031.19
    n-pentanol 787.73
    sec-butanol 1185.61
    n-hexane 385.57
    ethylene glycol 166.87
    NMP 1427.14
    cyclohexane 738.92
    DMSO 842.5
    n-butyl acetate 933.9
    n-octanol 682.95
    chloroform 2948.91
    n-propyl acetate 487.74
    acetic acid 854.9
    dichloromethane 1625.29
    cyclohexanone 1975.11
    propylene glycol 407.19
    isopropyl acetate 464.38
    DMAc 828.22
    2-ethoxyethanol 540.09
    isopentanol 885.82
    n-heptane 294.13
    ethyl formate 547.16
    1,2-dichloroethane 970.15
    n-hexanol 1406.29
    2-methoxyethanol 905.97
    isobutyl acetate 383.65
    tetrachloromethane 486.24
    n-pentyl acetate 517.0
    transcutol 1439.9
    n-heptanol 552.85
    ethylbenzene 444.28
    MIBK 535.31
    2-propoxyethanol 1153.55
    tert-butanol 1279.86
    MTBE 962.07
    2-butoxyethanol 606.9
    propionic acid 692.89
    o-xylene 440.38
    formic acid 179.21
    diethyl ether 867.68
    m-xylene 513.84
    p-xylene 542.67
    chlorobenzene 884.88
    dimethyl carbonate 206.12
    n-octane 116.79
    formamide 215.48
    cyclopentanone 1738.84
    2-pentanone 924.4
    anisole 614.42
    cyclopentyl methyl ether 1171.98
    gamma-butyrolactone 1464.73
    1-methoxy-2-propanol 904.36
    pyridine 1433.16
    3-pentanone 591.78
    furfural 1318.52
    n-dodecane 84.21
    diethylene glycol 612.48
    diisopropyl ether 316.53
    tert-amyl alcohol 1173.44
    acetylacetone 697.79
    n-hexadecane 97.2
    acetophenone 553.73
    methyl propionate 504.22
    isopentyl acetate 817.95
    trichloroethylene 2080.12
    n-nonanol 554.96
    cyclohexanol 1393.69
    benzyl alcohol 569.68
    2-ethylhexanol 773.83
    isooctanol 433.5
    dipropyl ether 602.68
    1,2-dichlorobenzene 685.88
    ethyl lactate 278.09
    propylene carbonate 1006.36
    n-methylformamide 562.94
    2-pentanol 903.71
    n-pentane 339.57
    1-propoxy-2-propanol 949.1
    1-methoxy-2-propyl acetate 656.68
    2-(2-methoxypropoxy) propanol 559.99
    mesitylene 338.72
    ε-caprolactone 1337.41
    p-cymene 339.38
    epichlorohydrin 1482.57
    1,1,1-trichloroethane 1376.79
    2-aminoethanol 437.34
    morpholine-4-carbaldehyde 1242.79
    sulfolane 1469.97
    2,2,4-trimethylpentane 143.2
    2-methyltetrahydrofuran 1869.08
    n-hexyl acetate 913.53
    isooctane 120.43
    2-(2-butoxyethoxy)ethanol 775.0
    sec-butyl acetate 387.33
    tert-butyl acetate 587.31
    decalin 229.63
    glycerin 388.24
    diglyme 1088.18
    acrylic acid 563.28
    isopropyl myristate 349.87
    n-butyric acid 1069.71
    acetyl acetate 419.7
    di(2-ethylhexyl) phthalate 325.47
    ethyl propionate 385.66
    nitromethane 985.43
    1,2-diethoxyethane 641.54
    benzonitrile 891.14
    trioctyl phosphate 244.51
    1-bromopropane 905.43
    gamma-valerolactone 1868.51
    n-decanol 404.16
    triethyl phosphate 259.12
    4-methyl-2-pentanol 451.11
    propionitrile 800.83
    vinylene carbonate 822.35
    1,1,2-trichlorotrifluoroethane 1011.53
    DMS 433.03
    cumene 298.07
    2-octanol 481.54
    2-hexanone 728.6
    octyl acetate 449.25
    limonene 562.29
    1,2-dimethoxyethane 1012.64
    ethyl orthosilicate 264.86
    tributyl phosphate 291.76
    diacetone alcohol 721.21
    N,N-dimethylaniline 406.69
    acrylonitrile 769.66
    aniline 741.74
    1,3-propanediol 650.21
    bromobenzene 912.76
    dibromomethane 1353.97
    1,1,2,2-tetrachloroethane 1828.31
    2-methyl-cyclohexyl acetate 554.54
    tetrabutyl urea 383.03
    diisobutyl methanol 402.79
    2-phenylethanol 743.42
    styrene 516.57
    dioctyl adipate 425.74
    dimethyl sulfate 298.74
    ethyl butyrate 502.39
    methyl lactate 325.36
    butyl lactate 468.76
    diethyl carbonate 342.9
    propanediol butyl ether 751.37
    triethyl orthoformate 395.52
    p-tert-butyltoluene 333.86
    methyl 4-tert-butylbenzoate 524.34
    morpholine 1957.94
    tert-butylamine 901.86
    n-dodecanol 300.8
    dimethoxymethane 639.13
    ethylene carbonate 701.43
    cyrene 532.72
    2-ethoxyethyl acetate 533.35
    2-ethylhexyl acetate 650.31
    1,2,4-trichlorobenzene 888.27
    4-methylpyridine 1543.88
    dibutyl ether 578.37
    2,6-dimethyl-4-heptanol 402.79
    DEF 754.45
    dimethyl isosorbide 898.67
    tetrachloroethylene 1076.09
    eugenol 522.14
    triacetin 536.23
    span 80 700.59
    1,4-butanediol 298.94
    1,1-dichloroethane 1348.4
    2-methyl-1-pentanol 702.25
    methyl formate 437.09
    2-methyl-1-butanol 881.6
    n-decane 148.08
    butyronitrile 1115.48
    3,7-dimethyl-1-octanol 594.91
    1-chlorooctane 458.46
    1-chlorotetradecane 187.16
    n-nonane 162.24
    undecane 108.44
    tert-butylcyclohexane 201.59
    cyclooctane 231.31
    cyclopentanol 1271.97
    tetrahydropyran 2191.55
    tert-amyl methyl ether 706.23
    2,5,8-trioxanonane 723.08
    1-hexene 822.53
    2-isopropoxyethanol 456.08
    2,2,2-trifluoroethanol 263.29
    methyl butyrate 572.69

    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
Galbanum 4 9000-24-2 Ferula galbaniflua Boiss. et Buhse, fam. Apiaceae (Umbelliferae) 0.01%