2-Vinyl-3,5-dimethylfuran

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  • Identifiers

    CAS number
    59417-62-8

    Molecular formula
    C8H10O

    SMILES
    CC1=CC(=C(O1)C=C)C

    Retention indicies (RI)

    • Carbowax: 1245.0

  • Odor profile

    Fragrance
    Nutty 52.88%
    Spicy 50.77%
    Roasted 49.04%
    Sweet 47.39%
    Green 45.49%
    Herbal 42.55%
    Musty 39.66%
    Burnt 36.86%
    Phenolic 34.81%
    Earthy 34.43%

     

    Flavor
    Nutty 51.12%
    Roasted 44.85%
    Cocoa 40.66%
    Burnt 35.31%
    Coffee 33.21%
    Musty 33.03%
    Meaty 31.81%
    Roast 30.88%
    Hazelnut 29.13%
    Earthy 28.58%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    7.09 (neutral)

    Molecular weight
    122.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    161°C

    Flash point

    • 26.25 ˚C est.

  • Synonyms

    • 2-vinyl-3,5-dimethylfuran
    • SCHEMBL3929231

  • Applications

    2‑Vinyl‑3,5‑dimethylfuran (CAS 59417‑62‑8) is a versatile, electron‑rich diene building block used in selective Diels–Alder constructions to access bicyclic frameworks, maleimide/anhydride adducts, and oxygenated polycycles for pharmaceutical and agrochemical discovery; its vinyl handle enables radical and controlled copolymerization with styrenics, acrylates, and maleimides to yield copolymers combining aromatic–heteroaromatic character for soft electronics, scratch‑resistant coatings, and curable networks; the reversible DA chemistry of the furan ring underpins self‑healing polymers, reworkable adhesives, and thermally triggered 3D‑printing resins; in materials chemistry it serves as a functional monomer for surface grafting, tuning energy levels in conjugated systems, and initiating light‑mediated grafting; in synthesis it is a convenient precursor for selective oxidation to conjugated aldehydes/ketones, ring‑opening to 1,4‑dicarbonyls, and transition‑metal‑mediated additions/couplings (Heck, hydroboration–oxidation, metathesis) to build libraries of substituted heterocycles; moreover, the furan motif aligns with green‑chemistry strategies via potential bio‑derived sourcing and provides a useful probe in mechanistic and spectroscopic studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1767.66
    methanol 2305.27
    isopropanol 1344.73
    water 23.88
    ethyl acetate 1399.34
    n-propanol 1614.4
    acetone 1366.11
    n-butanol 1720.23
    acetonitrile 1211.65
    DMF 1616.11
    toluene 1121.82
    isobutanol 1416.75
    1,4-dioxane 2828.65
    methyl acetate 1264.91
    THF 3179.89
    2-butanone 1343.93
    n-pentanol 1340.76
    sec-butanol 1507.37
    n-hexane 1052.03
    ethylene glycol 541.33
    NMP 1604.11
    cyclohexane 879.54
    DMSO 1339.2
    n-butyl acetate 1059.12
    n-octanol 942.49
    chloroform 3520.73
    n-propyl acetate 865.5
    acetic acid 793.56
    dichloromethane 3628.75
    cyclohexanone 1745.41
    propylene glycol 551.15
    isopropyl acetate 945.42
    DMAc 1386.89
    2-ethoxyethanol 1732.55
    isopentanol 1529.51
    n-heptane 522.55
    ethyl formate 816.26
    1,2-dichloroethane 2045.66
    n-hexanol 1657.01
    2-methoxyethanol 2170.85
    isobutyl acetate 636.72
    tetrachloromethane 1126.18
    n-pentyl acetate 834.92
    transcutol 2605.24
    n-heptanol 772.85
    ethylbenzene 727.5
    MIBK 1009.61
    2-propoxyethanol 2208.07
    tert-butanol 1697.21
    MTBE 1983.72
    2-butoxyethanol 1035.78
    propionic acid 844.31
    o-xylene 772.04
    formic acid 386.95
    diethyl ether 2510.77
    m-xylene 856.95
    p-xylene 820.15
    chlorobenzene 1140.51
    dimethyl carbonate 606.82
    n-octane 259.21
    formamide 438.75
    cyclopentanone 1780.42
    2-pentanone 1340.59
    anisole 1222.6
    cyclopentyl methyl ether 2190.82
    gamma-butyrolactone 1754.87
    1-methoxy-2-propanol 1707.81
    pyridine 1344.61
    3-pentanone 1172.78
    furfural 1368.29
    n-dodecane 194.47
    diethylene glycol 1369.94
    diisopropyl ether 936.26
    tert-amyl alcohol 1679.48
    acetylacetone 1132.85
    n-hexadecane 214.73
    acetophenone 781.4
    methyl propionate 1193.1
    isopentyl acetate 917.31
    trichloroethylene 2570.42
    n-nonanol 777.9
    cyclohexanol 1458.5
    benzyl alcohol 820.05
    2-ethylhexanol 968.48
    isooctanol 626.46
    dipropyl ether 1239.29
    1,2-dichlorobenzene 1020.86
    ethyl lactate 445.53
    propylene carbonate 903.34
    n-methylformamide 898.16
    2-pentanol 1337.92
    n-pentane 808.75
    1-propoxy-2-propanol 1295.72
    1-methoxy-2-propyl acetate 901.98
    2-(2-methoxypropoxy) propanol 797.39
    mesitylene 612.31
    ε-caprolactone 1485.9
    p-cymene 447.81
    epichlorohydrin 2452.7
    1,1,1-trichloroethane 2037.47
    2-aminoethanol 890.62
    morpholine-4-carbaldehyde 1772.07
    sulfolane 1862.97
    2,2,4-trimethylpentane 413.49
    2-methyltetrahydrofuran 2871.39
    n-hexyl acetate 1320.13
    isooctane 340.33
    2-(2-butoxyethoxy)ethanol 1162.84
    sec-butyl acetate 666.16
    tert-butyl acetate 1062.05
    decalin 475.07
    glycerin 680.42
    diglyme 1836.95
    acrylic acid 614.03
    isopropyl myristate 530.27
    n-butyric acid 1158.74
    acetyl acetate 682.06
    di(2-ethylhexyl) phthalate 408.03
    ethyl propionate 931.01
    nitromethane 1116.27
    1,2-diethoxyethane 1385.6
    benzonitrile 861.77
    trioctyl phosphate 344.04
    1-bromopropane 1851.16
    gamma-valerolactone 1948.47
    n-decanol 576.02
    triethyl phosphate 397.19
    4-methyl-2-pentanol 819.09
    propionitrile 1180.72
    vinylene carbonate 849.62
    1,1,2-trichlorotrifluoroethane 1133.34
    DMS 741.42
    cumene 565.56
    2-octanol 665.59
    2-hexanone 1041.61
    octyl acetate 656.53
    limonene 675.25
    1,2-dimethoxyethane 2361.28
    ethyl orthosilicate 432.14
    tributyl phosphate 411.35
    diacetone alcohol 1001.61
    N,N-dimethylaniline 901.93
    acrylonitrile 1080.2
    aniline 979.25
    1,3-propanediol 1147.31
    bromobenzene 1233.66
    dibromomethane 2746.7
    1,1,2,2-tetrachloroethane 2254.69
    2-methyl-cyclohexyl acetate 660.19
    tetrabutyl urea 496.33
    diisobutyl methanol 496.34
    2-phenylethanol 898.6
    styrene 817.04
    dioctyl adipate 581.38
    dimethyl sulfate 780.34
    ethyl butyrate 769.53
    methyl lactate 545.88
    butyl lactate 495.9
    diethyl carbonate 516.75
    propanediol butyl ether 817.85
    triethyl orthoformate 561.89
    p-tert-butyltoluene 470.52
    methyl 4-tert-butylbenzoate 770.8
    morpholine 2655.57
    tert-butylamine 1457.32
    n-dodecanol 453.9
    dimethoxymethane 1828.98
    ethylene carbonate 818.52
    cyrene 717.05
    2-ethoxyethyl acetate 928.88
    2-ethylhexyl acetate 785.24
    1,2,4-trichlorobenzene 1094.43
    4-methylpyridine 1576.75
    dibutyl ether 1101.28
    2,6-dimethyl-4-heptanol 496.34
    DEF 1466.4
    dimethyl isosorbide 1201.6
    tetrachloroethylene 1663.72
    eugenol 720.02
    triacetin 719.07
    span 80 674.6
    1,4-butanediol 701.31
    1,1-dichloroethane 2186.62
    2-methyl-1-pentanol 1330.45
    methyl formate 772.05
    2-methyl-1-butanol 1571.18
    n-decane 305.06
    butyronitrile 1368.64
    3,7-dimethyl-1-octanol 835.81
    1-chlorooctane 839.64
    1-chlorotetradecane 357.6
    n-nonane 347.15
    undecane 234.35
    tert-butylcyclohexane 509.84
    cyclooctane 443.19
    cyclopentanol 1414.29
    tetrahydropyran 2787.08
    tert-amyl methyl ether 1708.25
    2,5,8-trioxanonane 1215.25
    1-hexene 1569.56
    2-isopropoxyethanol 1256.67
    2,2,2-trifluoroethanol 364.82
    methyl butyrate 1019.84

    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
Mastic gum (Greece) 2 61789-92-2 Pistacia lentiscus L., var. Chia, fam. Anacardiaceae 0.01%