3-Butenyl isothiocyanate

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  • Identifiers

    CAS number
    3386-97-8

    Molecular formula
    C5H7NS

    SMILES
    C=CCCN=C=S

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1006.0
    • Carbowax: 1463.0

  • Odor profile

    Pungent 89.25%
    Green 83.67%
    Radish 80.62%
    Vegetable 42.57%
    Sulfurous 34.6%
    Cabbage 34.09%
    Alliaceous 33.66%
    Garlic 26.94%
    Metallic 26.62%
    Sharp 25.45%

    Scent© AI

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.18 (weak base)

    Molecular weight
    113.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point

    • 163.00 to 164.00 °C. @ 760.00 mm Hg

    Flash point est.
    61.86 ˚C

    Solubility expt.

    • 0.46 mg/mL at 20 °C
    • Very slightly soluble in water; freely soluble in ether
    • Soluble (in ethanol)

  • Synonyms

    • 3-Butenyl isothiocyanate
    • 3386-97-8
    • 4-isothiocyanatobut-1-ene
    • Isothiocyanic Acid 3-Buten-1-yl Ester
    • 1-Butene, 4-isothiocyanato-
    • 3-Buten-1-yl Isothiocyanate
    • Isothiocyanic acid, 3-butenyl ester
    • 4-Isothiocyanato-1-butene
    • UNII-13O98H1EW1
    • 13O98H1EW1
    • EINECS 222-209-8
    • But-3-enyl isothiocyanate
    • 1-Butene 4-isothiocyanate
    • CHEMBL3593942
    • FEMA NO. 4418
    • DTXSID30187494
    • 3-BUTENYL ISOTHIOCYANATE [FHFI]
    • Isothiocyanic acid, 3-butenyl ester (6CI,7CI,8CI); 4-Isothiocyanato-1-butene
    • MFCD00191660
    • 1-Butene-4-isothiocyanate
    • 4-Isothiocyanato-1-butene #
    • SCHEMBL434534
    • DTXCID40109985
    • CHEBI:138747
    • BDBM50104735
    • NSC782921
    • AKOS000276673
    • 4-Isothiocyanato-1-butene, AldrichCPR
    • NSC-782921
    • I0443
    • NS00022069
    • EN300-216195
    • Q27251535
    • Z1255360772
    • 222-209-8

  • Applications

    3-Butenyl isothiocyanate (CAS 3386-97-8) is a naturally occurring isothiocyanate formed from glucosinolate hydrolysis in Brassicaceae plants, used at trace levels in flavor formulations to impart pungent, sulfurous–green mustard/wasabi/horseradish notes; as a reference standard and comparator in analytical workflows (GC–MS/HPLC) for glucosinolate-derived volatiles; as a soft electrophile in organic synthesis to install an –NCS functionality or convert primary amines into thiourea derivatives for intermediates and surface/material functionalization; and in agricultural and life‑science research as a biofumigant component with antimicrobial, antifungal, insecticidal and nematicidal activity and as a probe of phase‑II enzyme induction, Nrf2/Keap1 signaling and protein thiol reactivity, with its volatility, sharp odor and irritancy motivating appropriate handling, packaging and formulation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 40.92
    methanol 37.28
    isopropanol 30.83
    water 0.05
    ethyl acetate 75.96
    n-propanol 33.68
    acetone 188.61
    n-butanol 33.81
    acetonitrile 85.73
    DMF 210.08
    toluene 89.01
    isobutanol 25.72
    1,4-dioxane 179.87
    methyl acetate 91.82
    THF 268.7
    2-butanone 117.03
    n-pentanol 34.38
    sec-butanol 31.78
    n-hexane 14.47
    ethylene glycol 10.65
    NMP 200.35
    cyclohexane 50.98
    DMSO 408.18
    n-butyl acetate 106.03
    n-octanol 34.49
    chloroform 354.41
    n-propyl acetate 73.22
    acetic acid 91.96
    dichloromethane 324.54
    cyclohexanone 172.33
    propylene glycol 16.97
    isopropyl acetate 44.93
    DMAc 176.98
    2-ethoxyethanol 61.26
    isopentanol 31.59
    n-heptane 19.98
    ethyl formate 56.38
    1,2-dichloroethane 217.99
    n-hexanol 43.42
    2-methoxyethanol 81.33
    isobutyl acetate 47.43
    tetrachloromethane 49.73
    n-pentyl acetate 55.08
    transcutol 384.94
    n-heptanol 23.45
    ethylbenzene 47.07
    MIBK 49.71
    2-propoxyethanol 76.31
    tert-butanol 49.43
    MTBE 57.75
    2-butoxyethanol 48.47
    propionic acid 41.55
    o-xylene 54.17
    formic acid 18.11
    diethyl ether 68.83
    m-xylene 50.02
    p-xylene 63.36
    chlorobenzene 138.52
    dimethyl carbonate 34.69
    n-octane 7.59
    formamide 35.38
    cyclopentanone 212.72
    2-pentanone 80.39
    anisole 96.09
    cyclopentyl methyl ether 96.43
    gamma-butyrolactone 163.77
    1-methoxy-2-propanol 59.17
    pyridine 246.51
    3-pentanone 73.46
    furfural 219.42
    n-dodecane 7.01
    diethylene glycol 60.86
    diisopropyl ether 22.31
    tert-amyl alcohol 40.89
    acetylacetone 123.15
    n-hexadecane 8.04
    acetophenone 96.81
    methyl propionate 59.45
    isopentyl acetate 81.76
    trichloroethylene 433.06
    n-nonanol 33.16
    cyclohexanol 50.5
    benzyl alcohol 65.93
    2-ethylhexanol 41.8
    isooctanol 21.6
    dipropyl ether 68.44
    1,2-dichlorobenzene 114.32
    ethyl lactate 32.43
    propylene carbonate 93.69
    n-methylformamide 62.19
    2-pentanol 26.1
    n-pentane 13.86
    1-propoxy-2-propanol 70.65
    1-methoxy-2-propyl acetate 90.43
    2-(2-methoxypropoxy) propanol 90.17
    mesitylene 33.84
    ε-caprolactone 109.57
    p-cymene 37.36
    epichlorohydrin 214.5
    1,1,1-trichloroethane 190.94
    2-aminoethanol 20.42
    morpholine-4-carbaldehyde 178.36
    sulfolane 239.12
    2,2,4-trimethylpentane 7.55
    2-methyltetrahydrofuran 150.39
    n-hexyl acetate 79.33
    isooctane 5.62
    2-(2-butoxyethoxy)ethanol 112.61
    sec-butyl acetate 45.26
    tert-butyl acetate 57.91
    decalin 17.3
    glycerin 26.38
    diglyme 222.22
    acrylic acid 48.61
    isopropyl myristate 39.92
    n-butyric acid 56.16
    acetyl acetate 75.15
    di(2-ethylhexyl) phthalate 42.76
    ethyl propionate 51.97
    nitromethane 175.32
    1,2-diethoxyethane 136.25
    benzonitrile 105.74
    trioctyl phosphate 27.17
    1-bromopropane 113.06
    gamma-valerolactone 195.21
    n-decanol 26.75
    triethyl phosphate 42.39
    4-methyl-2-pentanol 19.06
    propionitrile 56.18
    vinylene carbonate 88.95
    1,1,2-trichlorotrifluoroethane 160.02
    DMS 78.53
    cumene 30.22
    2-octanol 19.21
    2-hexanone 83.3
    octyl acetate 46.94
    limonene 58.16
    1,2-dimethoxyethane 166.76
    ethyl orthosilicate 40.99
    tributyl phosphate 36.92
    diacetone alcohol 64.56
    N,N-dimethylaniline 70.79
    acrylonitrile 80.13
    aniline 83.96
    1,3-propanediol 28.94
    bromobenzene 170.61
    dibromomethane 237.62
    1,1,2,2-tetrachloroethane 314.62
    2-methyl-cyclohexyl acetate 72.44
    tetrabutyl urea 58.01
    diisobutyl methanol 30.31
    2-phenylethanol 69.3
    styrene 74.3
    dioctyl adipate 68.58
    dimethyl sulfate 74.76
    ethyl butyrate 77.96
    methyl lactate 34.59
    butyl lactate 45.37
    diethyl carbonate 55.1
    propanediol butyl ether 57.14
    triethyl orthoformate 59.02
    p-tert-butyltoluene 35.61
    methyl 4-tert-butylbenzoate 69.11
    morpholine 164.83
    tert-butylamine 34.14
    n-dodecanol 23.17
    dimethoxymethane 98.26
    ethylene carbonate 62.95
    cyrene 78.26
    2-ethoxyethyl acetate 84.09
    2-ethylhexyl acetate 72.68
    1,2,4-trichlorobenzene 140.49
    4-methylpyridine 186.17
    dibutyl ether 72.34
    2,6-dimethyl-4-heptanol 30.31
    DEF 91.26
    dimethyl isosorbide 147.48
    tetrachloroethylene 180.72
    eugenol 72.74
    triacetin 92.93
    span 80 83.12
    1,4-butanediol 17.09
    1,1-dichloroethane 170.13
    2-methyl-1-pentanol 33.67
    methyl formate 61.66
    2-methyl-1-butanol 28.62
    n-decane 10.45
    butyronitrile 58.77
    3,7-dimethyl-1-octanol 41.03
    1-chlorooctane 39.19
    1-chlorotetradecane 18.73
    n-nonane 10.09
    undecane 8.19
    tert-butylcyclohexane 12.05
    cyclooctane 15.61
    cyclopentanol 53.26
    tetrahydropyran 167.71
    tert-amyl methyl ether 47.74
    2,5,8-trioxanonane 176.15
    1-hexene 41.38
    2-isopropoxyethanol 47.42
    2,2,2-trifluoroethanol 26.39
    methyl butyrate 74.87

    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
Horseradish Armoracia lapathifolia Gilib., fam. Brassicaceae (Cruciferae) 0.01%
Mustard seed (China) 2 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 0.18%
Kohlrabi, green (seed) Brassica oleraceae var. gongylodes, fam. Brassicaceae (Cruciferae) 27.6%
Rocket leaf 1 Eruca sativa L., fam. Brassicaceae 0.04%