4-Pentenyl isothiocyanate

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  • Identifiers

    CAS number
    18060-79-2

    Molecular formula
    C6H9NS

    SMILES
    C=CCCCN=C=S

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1086.0

  • Odor profile

    Green 88.11%
    Pungent 86.02%
    Radish 77.73%
    Vegetable 45.96%
    Fatty 36.49%
    Cabbage 34.5%
    Sulfurous 31.18%
    Metallic 28.9%
    Alliaceous 26.85%
    Tomato 24.05%

    Scent© AI

  • Properties

    XLogP3-AA
    3.1

    Molecular weight
    127.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point

    • 182.00 to 183.00 °C. @ 760.00 mm Hg

    Flash point est.
    66.25 ˚C

    Solubility expt.

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

  • Synonyms

    • 4-Pentenyl isothiocyanate
    • 18060-79-2
    • 5-isothiocyanatopent-1-ene
    • 1-Pentene, 5-isothiocyanato-
    • Isothiocyanic Acid 4-Penten-1-yl Ester
    • 4-Penten-1-yl Isothiocyanate
    • 5-Isothiocyanato-1-pentene
    • 5-isothiocyano-1-pentene
    • UNII-HL8X1CRR9B
    • HL8X1CRR9B
    • CHEMBL3593943
    • FEMA NO. 4427
    • DBISBKDNOKIADM-UHFFFAOYSA-
    • DTXSID70170986
    • 4-PENTENYL ISOTHIOCYANATE [FHFI]
    • ISOTHIOCYANIC ACID, 4-PENTENYL ESTER
    • MFCD00191527
    • SCHEMBL1647187
    • DTXCID0093477
    • CHEBI:138749
    • BDBM50104734
    • NSC782922
    • AKOS025294758
    • HY-W269799
    • NSC-782922
    • BS-43918
    • DB-044400
    • CS-0315092
    • I0444
    • NS00120923
    • T71958
    • Q27279987

  • Applications

    4-Pentenyl isothiocyanate (CAS 18060-79-2) is a versatile electrophile used to install isothiocyanate functionality via rapid thiourea formation with amines for drug discovery, as a reactive probe for nucleophilic residues on proteins (cysteine/lysine) in chemical biology, and for amine derivatization in LC–MS; its terminal alkene enables orthogonal transformations such as thiol–ene coupling, olefin metathesis, hydroboration–oxidation, and epoxidation, allowing construction of bifunctional linkers, crosslinkable polymer networks, surface/nanomaterial immobilization, and post-polymerization modification; it serves as a building block to access sulfur-containing heterocycles and urea/thiourea scaffolds, to optimize antimicrobial, antifungal, insecticidal, and anticancer leads in agrochemical–pharmaceutical research, and as a model for natural isothiocyanates (e.g., allyl/sulforaphane) in mechanistic and flavor–sensory studies; leveraging both the –N=C=S and alkene handles, it supports sensor development via thiourea chemistry, soft covalent protein labeling, and photo/chemically crosslinkable materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 48.18
    methanol 53.3
    isopropanol 30.78
    water 0.11
    ethyl acetate 83.8
    n-propanol 41.91
    acetone 175.87
    n-butanol 39.79
    acetonitrile 75.72
    DMF 285.81
    toluene 93.96
    isobutanol 30.2
    1,4-dioxane 214.33
    methyl acetate 91.95
    THF 281.83
    2-butanone 116.85
    n-pentanol 39.22
    sec-butanol 32.39
    n-hexane 10.41
    ethylene glycol 16.63
    NMP 246.93
    cyclohexane 30.21
    DMSO 314.62
    n-butyl acetate 94.89
    n-octanol 17.54
    chloroform 313.12
    n-propyl acetate 71.49
    acetic acid 99.6
    dichloromethane 272.41
    cyclohexanone 162.19
    propylene glycol 18.85
    isopropyl acetate 52.75
    DMAc 249.63
    2-ethoxyethanol 78.63
    isopentanol 38.35
    n-heptane 10.02
    ethyl formate 54.76
    1,2-dichloroethane 215.74
    n-hexanol 44.17
    2-methoxyethanol 110.38
    isobutyl acetate 51.37
    tetrachloromethane 48.78
    n-pentyl acetate 42.51
    transcutol 358.43
    n-heptanol 18.6
    ethylbenzene 40.28
    MIBK 54.44
    2-propoxyethanol 95.61
    tert-butanol 47.57
    MTBE 70.1
    2-butoxyethanol 48.99
    propionic acid 45.49
    o-xylene 54.12
    formic acid 30.12
    diethyl ether 80.32
    m-xylene 49.49
    p-xylene 53.99
    chlorobenzene 137.73
    dimethyl carbonate 44.75
    n-octane 2.98
    formamide 47.92
    cyclopentanone 205.36
    2-pentanone 86.14
    anisole 99.84
    cyclopentyl methyl ether 96.09
    gamma-butyrolactone 169.72
    1-methoxy-2-propanol 68.78
    pyridine 246.84
    3-pentanone 82.12
    furfural 248.19
    n-dodecane 2.53
    diethylene glycol 80.92
    diisopropyl ether 23.19
    tert-amyl alcohol 42.44
    acetylacetone 135.05
    n-hexadecane 2.96
    acetophenone 104.0
    methyl propionate 67.18
    isopentyl acetate 81.22
    trichloroethylene 447.64
    n-nonanol 18.46
    cyclohexanol 45.27
    benzyl alcohol 67.97
    2-ethylhexanol 35.21
    isooctanol 16.93
    dipropyl ether 58.14
    1,2-dichlorobenzene 124.18
    ethyl lactate 34.52
    propylene carbonate 88.94
    n-methylformamide 73.13
    2-pentanol 25.71
    n-pentane 10.38
    1-propoxy-2-propanol 68.47
    1-methoxy-2-propyl acetate 102.7
    2-(2-methoxypropoxy) propanol 83.48
    mesitylene 32.39
    ε-caprolactone 114.55
    p-cymene 29.7
    epichlorohydrin 232.51
    1,1,1-trichloroethane 174.65
    2-aminoethanol 28.08
    morpholine-4-carbaldehyde 232.22
    sulfolane 238.81
    2,2,4-trimethylpentane 7.25
    2-methyltetrahydrofuran 150.45
    n-hexyl acetate 51.57
    isooctane 4.85
    2-(2-butoxyethoxy)ethanol 96.56
    sec-butyl acetate 48.2
    tert-butyl acetate 65.2
    decalin 12.22
    glycerin 35.13
    diglyme 201.91
    acrylic acid 56.74
    isopropyl myristate 26.06
    n-butyric acid 64.16
    acetyl acetate 82.67
    di(2-ethylhexyl) phthalate 34.89
    ethyl propionate 54.06
    nitromethane 188.8
    1,2-diethoxyethane 129.37
    benzonitrile 97.27
    trioctyl phosphate 19.48
    1-bromopropane 98.25
    gamma-valerolactone 240.61
    n-decanol 14.33
    triethyl phosphate 38.79
    4-methyl-2-pentanol 19.42
    propionitrile 53.58
    vinylene carbonate 93.46
    1,1,2-trichlorotrifluoroethane 192.37
    DMS 81.46
    cumene 26.52
    2-octanol 11.56
    2-hexanone 78.49
    octyl acetate 30.72
    limonene 45.54
    1,2-dimethoxyethane 178.54
    ethyl orthosilicate 37.18
    tributyl phosphate 28.55
    diacetone alcohol 66.02
    N,N-dimethylaniline 71.98
    acrylonitrile 74.67
    aniline 83.28
    1,3-propanediol 38.25
    bromobenzene 164.77
    dibromomethane 181.59
    1,1,2,2-tetrachloroethane 305.79
    2-methyl-cyclohexyl acetate 65.39
    tetrabutyl urea 41.94
    diisobutyl methanol 23.39
    2-phenylethanol 72.89
    styrene 66.54
    dioctyl adipate 50.91
    dimethyl sulfate 88.04
    ethyl butyrate 69.44
    methyl lactate 40.54
    butyl lactate 37.24
    diethyl carbonate 48.2
    propanediol butyl ether 46.25
    triethyl orthoformate 54.94
    p-tert-butyltoluene 27.67
    methyl 4-tert-butylbenzoate 60.67
    morpholine 200.44
    tert-butylamine 32.8
    n-dodecanol 11.83
    dimethoxymethane 123.66
    ethylene carbonate 69.19
    cyrene 83.36
    2-ethoxyethyl acetate 80.56
    2-ethylhexyl acetate 70.3
    1,2,4-trichlorobenzene 166.03
    4-methylpyridine 185.7
    dibutyl ether 39.02
    2,6-dimethyl-4-heptanol 23.39
    DEF 109.8
    dimethyl isosorbide 149.52
    tetrachloroethylene 206.65
    eugenol 71.88
    triacetin 79.31
    span 80 62.11
    1,4-butanediol 19.39
    1,1-dichloroethane 148.72
    2-methyl-1-pentanol 39.43
    methyl formate 66.35
    2-methyl-1-butanol 34.9
    n-decane 3.75
    butyronitrile 55.68
    3,7-dimethyl-1-octanol 24.84
    1-chlorooctane 18.67
    1-chlorotetradecane 9.19
    n-nonane 3.37
    undecane 2.98
    tert-butylcyclohexane 9.3
    cyclooctane 9.06
    cyclopentanol 49.93
    tetrahydropyran 173.51
    tert-amyl methyl ether 54.49
    2,5,8-trioxanonane 159.92
    1-hexene 34.86
    2-isopropoxyethanol 56.13
    2,2,2-trifluoroethanol 34.44
    methyl butyrate 72.76

    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) 2.3%
Kohlrabi, green (seed) Brassica oleraceae var. gongylodes, fam. Brassicaceae (Cruciferae) 0.1%
Rocket leaf 2 headspace Eruca sativa L., fam. Brassicaceae 3.2%