Tetrahydro-5-isopropenyl-2-methyl-2-vinylfuran

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    13679-86-2

    Molecular formula
    C10H16O

    SMILES
    CC(=C)C1CCC(O1)(C)C=C

    Safety labels

    Flammable
    Flammable

  • Odor profile

    Herbal 85.75%
    Green 77.69%
    Mint 76.52%
    Fresh 67.51%
    Spicy 58.83%
    Cooling 56.8%
    Camphoreous 55.34%
    Citrus 52.71%
    Sweet 51.85%
    Woody 51.18%

    Scent© AI

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.82 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    171°C

    Flash point est.
    46.58 ˚C

    Solubility expt.

    • Soluble in oils
    • Soluble (in ethanol)

  • Synonyms

    • 13679-86-2
    • 2-Isopropenyl-5-methyl-5-vinyltetrahydrofuran
    • Furan, 2-ethenyltetrahydro-2-methyl-5-(1-methylethenyl)-
    • 2-ethenyl-2-methyl-5-prop-1-en-2-yloxolane
    • Anhydrolinalool oxide
    • Dehydroxylinalool Oxide
    • Tetrahydro-5-isopropenyl-2-methyl-2-vinylfuran
    • cis-anhydro linalool oxide
    • 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran
    • 2-Ethenyltetrahydro-2-methyl-5-(1-methylethenyl)furan
    • 2-Methyl-2-vinyl-5-isopropenyltetrahydrofuran
    • 2-ethenyl-2-methyl-5-(prop-1-en-2-yl)oxolane
    • 2-Ethenyl-2-methyl-5-(1-methylethenyl)tetrahydrofuran
    • UNII-F2S8JZM40P
    • FEMA No. 3759
    • FEMA 3759
    • EINECS 237-184-9
    • MFCD00065422
    • F2S8JZM40P
    • Furan, tetrahydro-5-isopropenyl-2-methyl-2-vinyl-
    • SCHEMBL872776
    • 2-methyl-5-(prop-1-en-2-yl)-2-vinyltetrahydrofuran
    • 5-ISOPROPENYL-2-METHYL-2-VINYL TETRAHYDROFURAN
    • FEMA3759
    • DTXSID20864429
    • CHEBI:171918
    • AKOS006283215
    • 5-Isopropenyl-2-methyl-2-vinyl-oxolan
    • BS-20804
    • DB-042357
    • CS-0205438
    • I0744
    • NS00013210
    • D91198
    • Tetrahydro-5-isopropenyl-2-methyl-2-vinyl-Furan
    • 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran, 9CI
    • Q67879781
    • 2-Ethenyltetrahydro-2-methyl-5-(1-methylethenyl)-Furan
    • 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran, AldrichCPR
    • (2R,5S)-2-Methyl-5-(prop-1-en-2-yl)-2-vinyltetrahydrofuran
    • 2-Ethenyltetrahydro-2-methyl-5-(1-methylethenyl)furan, 9CI

  • Applications

    Tetrahydro-5-isopropenyl-2-methyl-2-vinylfuran is used as a versatile terpenoid building block in fine organic synthesis (intermediate for flavors and fragrances, precursor to functionalized tetrahydrofuran scaffolds in pharma and agrochemical discovery), as a reactive diluent/monomer or crosslinker bearing two alkenes for UV- and thermally curable coatings, inks and 3D-printing resins (thiol–ene click, free-radical polymerization, hydrosilylation, olefin metathesis), as a substrate for selective transformations (epoxidation, hydroboration–oxidation, ozonolysis, hydroformylation) to access polyfunctional derivatives, in surface modification and photografting to improve adhesion, and as a model substrate in studies of radical additions and alkene functionalization; in fragrance research, its derivatives can impart fresh, green citrus–woody furan-terpene nuances to experimental accords.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 759.57
    methanol 625.17
    isopropanol 791.81
    water 4.57
    ethyl acetate 624.07
    n-propanol 727.32
    acetone 434.03
    n-butanol 826.68
    acetonitrile 589.2
    DMF 415.33
    toluene 610.4
    isobutanol 694.94
    1,4-dioxane 1035.18
    methyl acetate 558.22
    THF 1092.45
    2-butanone 635.0
    n-pentanol 619.41
    sec-butanol 839.37
    n-hexane 254.26
    ethylene glycol 156.31
    NMP 406.1
    cyclohexane 307.77
    DMSO 357.56
    n-butyl acetate 633.82
    n-octanol 584.34
    chloroform 2351.96
    n-propyl acetate 370.88
    acetic acid 328.53
    dichloromethane 1735.51
    cyclohexanone 686.28
    propylene glycol 304.89
    isopropyl acetate 459.77
    DMAc 593.74
    2-ethoxyethanol 573.61
    isopentanol 789.0
    n-heptane 270.85
    ethyl formate 374.89
    1,2-dichloroethane 711.13
    n-hexanol 1009.22
    2-methoxyethanol 657.53
    isobutyl acetate 308.62
    tetrachloromethane 516.02
    n-pentyl acetate 417.14
    transcutol 1399.82
    n-heptanol 499.34
    ethylbenzene 397.79
    MIBK 426.54
    2-propoxyethanol 900.11
    tert-butanol 944.28
    MTBE 895.63
    2-butoxyethanol 579.49
    propionic acid 394.22
    o-xylene 442.88
    formic acid 115.19
    diethyl ether 761.28
    m-xylene 460.53
    p-xylene 490.38
    chlorobenzene 573.15
    dimethyl carbonate 170.34
    n-octane 111.48
    formamide 151.28
    cyclopentanone 575.87
    2-pentanone 524.11
    anisole 591.58
    cyclopentyl methyl ether 661.05
    gamma-butyrolactone 538.76
    1-methoxy-2-propanol 668.03
    pyridine 693.56
    3-pentanone 436.92
    furfural 581.38
    n-dodecane 105.29
    diethylene glycol 497.12
    diisopropyl ether 318.13
    tert-amyl alcohol 843.63
    acetylacetone 460.57
    n-hexadecane 114.24
    acetophenone 451.89
    methyl propionate 410.17
    isopentyl acetate 626.15
    trichloroethylene 1178.52
    n-nonanol 485.08
    cyclohexanol 661.53
    benzyl alcohol 469.47
    2-ethylhexanol 616.68
    isooctanol 391.11
    dipropyl ether 556.87
    1,2-dichlorobenzene 535.87
    ethyl lactate 218.57
    propylene carbonate 444.27
    n-methylformamide 249.1
    2-pentanol 660.78
    n-pentane 254.52
    1-propoxy-2-propanol 706.62
    1-methoxy-2-propyl acetate 533.06
    2-(2-methoxypropoxy) propanol 564.33
    mesitylene 313.75
    ε-caprolactone 652.73
    p-cymene 348.82
    epichlorohydrin 811.48
    1,1,1-trichloroethane 986.2
    2-aminoethanol 361.43
    morpholine-4-carbaldehyde 609.33
    sulfolane 495.41
    2,2,4-trimethylpentane 158.57
    2-methyltetrahydrofuran 1005.04
    n-hexyl acetate 666.52
    isooctane 129.47
    2-(2-butoxyethoxy)ethanol 691.68
    sec-butyl acetate 336.58
    tert-butyl acetate 478.22
    decalin 176.55
    glycerin 286.42
    diglyme 1041.61
    acrylic acid 277.92
    isopropyl myristate 334.5
    n-butyric acid 573.68
    acetyl acetate 364.45
    di(2-ethylhexyl) phthalate 279.62
    ethyl propionate 362.48
    nitromethane 398.91
    1,2-diethoxyethane 662.47
    benzonitrile 600.95
    trioctyl phosphate 212.57
    1-bromopropane 839.05
    gamma-valerolactone 686.39
    n-decanol 361.17
    triethyl phosphate 238.94
    4-methyl-2-pentanol 444.16
    propionitrile 624.7
    vinylene carbonate 433.53
    1,1,2-trichlorotrifluoroethane 526.65
    DMS 355.38
    cumene 319.44
    2-octanol 379.04
    2-hexanone 439.33
    octyl acetate 396.77
    limonene 465.11
    1,2-dimethoxyethane 832.1
    ethyl orthosilicate 249.44
    tributyl phosphate 244.55
    diacetone alcohol 469.12
    N,N-dimethylaniline 457.13
    acrylonitrile 514.4
    aniline 556.27
    1,3-propanediol 446.1
    bromobenzene 640.68
    dibromomethane 1255.41
    1,1,2,2-tetrachloroethane 1086.7
    2-methyl-cyclohexyl acetate 433.7
    tetrabutyl urea 279.59
    diisobutyl methanol 331.61
    2-phenylethanol 553.49
    styrene 426.92
    dioctyl adipate 365.32
    dimethyl sulfate 210.76
    ethyl butyrate 481.22
    methyl lactate 221.8
    butyl lactate 306.25
    diethyl carbonate 333.5
    propanediol butyl ether 513.0
    triethyl orthoformate 350.04
    p-tert-butyltoluene 335.94
    methyl 4-tert-butylbenzoate 471.58
    morpholine 1008.22
    tert-butylamine 793.06
    n-dodecanol 289.18
    dimethoxymethane 410.21
    ethylene carbonate 379.62
    cyrene 367.84
    2-ethoxyethyl acetate 459.38
    2-ethylhexyl acetate 518.91
    1,2,4-trichlorobenzene 598.62
    4-methylpyridine 805.91
    dibutyl ether 541.4
    2,6-dimethyl-4-heptanol 331.61
    DEF 482.87
    dimethyl isosorbide 725.53
    tetrachloroethylene 667.58
    eugenol 415.57
    triacetin 499.94
    span 80 503.95
    1,4-butanediol 250.96
    1,1-dichloroethane 992.75
    2-methyl-1-pentanol 618.6
    methyl formate 182.8
    2-methyl-1-butanol 742.8
    n-decane 159.68
    butyronitrile 775.3
    3,7-dimethyl-1-octanol 551.97
    1-chlorooctane 410.14
    1-chlorotetradecane 191.15
    n-nonane 160.44
    undecane 124.83
    tert-butylcyclohexane 190.42
    cyclooctane 139.09
    cyclopentanol 595.15
    tetrahydropyran 1024.69
    tert-amyl methyl ether 651.84
    2,5,8-trioxanonane 748.72
    1-hexene 524.18
    2-isopropoxyethanol 482.38
    2,2,2-trifluoroethanol 143.51
    methyl butyrate 427.1

    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
Aristolochia asclepiadifolia root Aristolochia asclepiadifolia, fam. Aristolochiaceae 0.02%
Lemon balm (Spain) 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Bergamot (Italy) 3 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bitter orange leaf (Petitgrain) (Spain) 1 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.1%
Clary sage (U.S.A.) 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 0.1%
Clary sage (France) 2 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 0.01%
Clary sage (Russia) 1 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 0.01%
Rhus coriaria Rhus coriaria L., fam. Anarcadiaceae 0.02%
Ho leaf (Japan) 1a 8022-91-1 Cinnamomum camphora Sieb. linaloolifera Fujita, fam. Lauraceae 2.65%
Ho leaf (Japan) 1b 8022-91-1 Cinnamomum camphora Sieb. linaloolifera Fujita, fam. Lauraceae 0.4%
Lime (Mexican, West Indian, Key) (Peru) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.24%
Lime (Mexican, West Indian, Key) (Ivory Coast) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.18%
Lime (Mexican, West Indian, Key) 7 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.03%
Lemon balm (Italy) 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.01%
Myrtle leaf (Turkey) 2 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.1%