Bornylene

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  • Identifiers

    CAS number
    464-17-5

    Molecular formula
    C10H16

    SMILES
    CC1(C2CCC1(C=C2)C)C

    Retention indicies (RI)

    • DB5: 902.0
    • Carbowax: 976.0

  • Odor profile

    Woody 85.68%
    Sweet 52.67%
    Dry 47.67%
    Spicy 47.46%
    Fresh 45.37%
    Green 45.17%
    Herbal 44.93%
    Terpenic 42.07%
    Pine 41.11%
    Camphoreous 40.49%

    Scent© AI

  • Properties

    XLogP3-AA
    3.6

    Molecular weight
    136.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    144°C

    Flash point est.
    29.66 ˚C

  • Synonyms

    • Bornylene
    • 2-Bornene
    • 464-17-5
    • 1,7,7-Trimethylnorbornene
    • 1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPT-2-ENE
    • 1,7,7-Trimethyl-2-norbornene
    • F7WB27RKZC
    • 1,7,7-Trimethylbicyclo(2.2.1)hept-2-ene
    • .ALPHA.-BORNENE
    • UNII-F7WB27RKZC
    • Bicyclo[2.2.1]hept-2-ene, 1,7,7-trimethyl-
    • NSC 193373
    • NSC-193373
    • DTXSID20870545
    • Bicyclo(2.2.1)hept-2-ene, 1,7,7-trimethyl-
    • 2-Bornene (8CI)
    • bornene
    • ALPHA-BORNENE
    • 1,7-Trimethylnorbornene
    • 1,7-Trimethyl-2-norbornene
    • DTXCID80818261
    • TAA38334
    • NSC193373
    • 1,7-Trimethylbicyclo[2.2.1]hept-2-ene
    • Bicyclo[2.2.1]hept-2-ene,7,7-trimethyl-
    • NS00010213
    • EN300-296428
    • Q27277780
    • Bicyclo(2.2.1)hept-2-ene, 1,7,7-trimethyl-(9CI)

  • Applications

    Bornylene (CAS 464-17-5) is a bicyclic monoterpene seldom manufactured at scale, used mainly in research and synthesis: as a substrate/mechanistic probe for nonclassical carbocation chemistry (bornyl–bornylenyl rearrangements), electrophilic additions, epoxidation to bornylene oxide, hydroboration–oxidation, ozonolysis, and other terpene transformations to study stereoselectivity and ring strain; practically, it serves as a building block to access functionalized monoterpenes (borneol/isoborneol-type and camphor-family derivatives), as an intermediate toward terpenoid fragrance/flavor ingredients, a precursor to chiral epoxides/diols, and a model substrate for catalyst and asymmetric method development; on a limited scale, bornylene and its derivatives may also be used as niche mono/co-monomers in materials chemistry or as highly hydrophobic components in extraction studies, but direct industrial use remains modest and is often supplanted by more abundant terpenes such as camphene or α-pinene.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 356.35
    methanol 357.09
    isopropanol 325.93
    water 5.73
    ethyl acetate 656.87
    n-propanol 348.59
    acetone 481.15
    n-butanol 344.58
    acetonitrile 491.14
    DMF 581.24
    toluene 511.96
    isobutanol 276.72
    1,4-dioxane 1053.73
    methyl acetate 617.18
    THF 944.13
    2-butanone 499.63
    n-pentanol 218.33
    sec-butanol 326.21
    n-hexane 148.62
    ethylene glycol 96.31
    NMP 315.59
    cyclohexane 191.02
    DMSO 273.06
    n-butyl acetate 439.07
    n-octanol 216.36
    chloroform 1101.74
    n-propyl acetate 315.08
    acetic acid 242.23
    dichloromethane 811.09
    cyclohexanone 450.51
    propylene glycol 140.07
    isopropyl acetate 543.78
    DMAc 564.2
    2-ethoxyethanol 348.25
    isopentanol 320.8
    n-heptane 136.76
    ethyl formate 299.49
    1,2-dichloroethane 519.29
    n-hexanol 352.54
    2-methoxyethanol 497.36
    isobutyl acetate 269.08
    tetrachloromethane 395.68
    n-pentyl acetate 273.16
    transcutol 1075.53
    n-heptanol 221.67
    ethylbenzene 341.78
    MIBK 392.14
    2-propoxyethanol 554.52
    tert-butanol 417.99
    MTBE 650.66
    2-butoxyethanol 349.8
    propionic acid 265.4
    o-xylene 382.89
    formic acid 115.8
    diethyl ether 616.53
    m-xylene 425.96
    p-xylene 484.61
    chlorobenzene 464.35
    dimethyl carbonate 336.21
    n-octane 69.88
    formamide 272.21
    cyclopentanone 497.24
    2-pentanone 419.34
    anisole 625.18
    cyclopentyl methyl ether 506.78
    gamma-butyrolactone 503.58
    1-methoxy-2-propanol 466.15
    pyridine 649.94
    3-pentanone 420.1
    furfural 497.89
    n-dodecane 53.38
    diethylene glycol 336.38
    diisopropyl ether 361.35
    tert-amyl alcohol 368.22
    acetylacetone 579.28
    n-hexadecane 60.7
    acetophenone 415.89
    methyl propionate 488.11
    isopentyl acetate 448.05
    trichloroethylene 818.96
    n-nonanol 224.97
    cyclohexanol 271.34
    benzyl alcohol 304.67
    2-ethylhexanol 266.93
    isooctanol 207.48
    dipropyl ether 434.54
    1,2-dichlorobenzene 466.96
    ethyl lactate 158.72
    propylene carbonate 347.26
    n-methylformamide 328.94
    2-pentanol 293.56
    n-pentane 155.6
    1-propoxy-2-propanol 453.2
    1-methoxy-2-propyl acetate 589.06
    2-(2-methoxypropoxy) propanol 405.12
    mesitylene 345.61
    ε-caprolactone 425.43
    p-cymene 273.03
    epichlorohydrin 610.52
    1,1,1-trichloroethane 764.89
    2-aminoethanol 205.08
    morpholine-4-carbaldehyde 599.26
    sulfolane 353.4
    2,2,4-trimethylpentane 102.8
    2-methyltetrahydrofuran 622.19
    n-hexyl acetate 370.03
    isooctane 111.1
    2-(2-butoxyethoxy)ethanol 479.58
    sec-butyl acetate 318.54
    tert-butyl acetate 593.56
    decalin 143.49
    glycerin 166.21
    diglyme 834.14
    acrylic acid 215.71
    isopropyl myristate 220.54
    n-butyric acid 354.25
    acetyl acetate 533.13
    di(2-ethylhexyl) phthalate 179.42
    ethyl propionate 377.6
    nitromethane 479.93
    1,2-diethoxyethane 655.91
    benzonitrile 351.91
    trioctyl phosphate 123.35
    1-bromopropane 409.89
    gamma-valerolactone 660.58
    n-decanol 180.38
    triethyl phosphate 219.1
    4-methyl-2-pentanol 263.47
    propionitrile 448.08
    vinylene carbonate 387.51
    1,1,2-trichlorotrifluoroethane 374.56
    DMS 410.47
    cumene 287.19
    2-octanol 160.8
    2-hexanone 299.75
    octyl acetate 239.48
    limonene 295.82
    1,2-dimethoxyethane 680.74
    ethyl orthosilicate 237.54
    tributyl phosphate 154.68
    diacetone alcohol 417.64
    N,N-dimethylaniline 440.02
    acrylonitrile 465.87
    aniline 473.15
    1,3-propanediol 282.14
    bromobenzene 543.5
    dibromomethane 558.65
    1,1,2,2-tetrachloroethane 693.51
    2-methyl-cyclohexyl acetate 313.43
    tetrabutyl urea 172.05
    diisobutyl methanol 221.92
    2-phenylethanol 383.55
    styrene 377.34
    dioctyl adipate 248.83
    dimethyl sulfate 324.2
    ethyl butyrate 406.09
    methyl lactate 230.93
    butyl lactate 200.3
    diethyl carbonate 313.8
    propanediol butyl ether 243.69
    triethyl orthoformate 333.63
    p-tert-butyltoluene 297.44
    methyl 4-tert-butylbenzoate 411.22
    morpholine 866.53
    tert-butylamine 364.05
    n-dodecanol 144.76
    dimethoxymethane 597.26
    ethylene carbonate 363.38
    cyrene 227.75
    2-ethoxyethyl acetate 425.53
    2-ethylhexyl acetate 381.9
    1,2,4-trichlorobenzene 490.25
    4-methylpyridine 624.94
    dibutyl ether 315.66
    2,6-dimethyl-4-heptanol 221.92
    DEF 425.63
    dimethyl isosorbide 607.6
    tetrachloroethylene 535.58
    eugenol 340.46
    triacetin 388.95
    span 80 302.69
    1,4-butanediol 113.24
    1,1-dichloroethane 633.45
    2-methyl-1-pentanol 230.52
    methyl formate 240.04
    2-methyl-1-butanol 294.91
    n-decane 83.92
    butyronitrile 372.26
    3,7-dimethyl-1-octanol 270.47
    1-chlorooctane 193.98
    1-chlorotetradecane 108.65
    n-nonane 77.1
    undecane 65.26
    tert-butylcyclohexane 146.06
    cyclooctane 121.95
    cyclopentanol 259.88
    tetrahydropyran 724.38
    tert-amyl methyl ether 467.83
    2,5,8-trioxanonane 625.59
    1-hexene 266.64
    2-isopropoxyethanol 281.27
    2,2,2-trifluoroethanol 174.95
    methyl butyrate 370.26

    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
Abies cephalonica Abies cephalonica Loud., fam. Pinaceae 0.05%
Shanqiu Anaphalis margaritacea (L.) Benth.et Hook.(Shanqiu),fam.Asteraceae (Comp.) 0.47%
Rhanterium Rhanterium epapposum Oliv. 0.15%
Zingiber cassumunar root (Indonesia) 1 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.01%
Zingiber cassumunar root (Indonesia) 2 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.7%
Annual wormwood (France) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.01%
Cypress (Algeria) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.01%
Betel leaf Sanchi (India) Piper betle L. var. Sanchi, fam. Piperaceae 1.18%
Pinus koraiensis (China) Pinus koraiensis Sieb. et Zucc., fam. Pinaceae 0.26%
Styrax (China) 8024-01-9 Liquidamber formosana Hance, fam. Hamamelidaceae 0.14%
Dendrobium chrysatoxum flower (China) Dendrobium chrysatoxum Lindl., fam. Orchidaceae 1.11%
Ocimum gratissimum (India) 1 Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 0.56%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.02%
Lippia scaberrima (South Africa) 1a Lippia scaberrima Sond., fam. Verbeneceae (local: Beukesbossie) 0.25%
Lippia scaberrima (South Africa) 1b Lippia scaberrima Sond., fam. Verbenaceae (local: Beukesbossie) 0.05%
Cypress, Leyland (Poland) Cupressocyparis leylandii (Dall. et Jacks.) Dall., fam. Cupressaceae 0.01%