Bicyclo[2.2.2]oct-5-ene-2-carbonitrile, 5-methyl-7-(1-methylethyl)-

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  • Identifiers

    CAS number
    68311-05-7

    Molecular formula
    C13H19N

    SMILES
    CC1=CC2C(CC1CC2C(C)C)C#N

  • Odor profile

    Fragrance
    Green 73.89%
    Woody 65.85%
    Spicy 53.92%
    Herbal 43.91%
    Leafy 34.34%
    Earthy 31.91%
    Citrus 31.84%
    Fresh 30.34%
    Aldehydic 27.16%
    Dry 25.82%

     

    Flavor
    Herbal 38.77%
    Bitter 35.74%
    Herb 33.11%
    Woody 31.83%
    Wood 28.19%
    Spice 27.25%
    Cedarleaf 22.29%
    Terpentine 21.53%
    Green tea 20.36%
    Sandalwood 20.05%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    8.18 (weak base)

    Molecular weight
    189.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    289°C

    Flash point

    • 108.06 ˚C est.

  • Synonyms

    • 68311-05-7
    • EINECS 269-744-3
    • Bicyclo[2.2.2]oct-5-ene-2-carbonitrile, 5-methyl-7-(1-methylethyl)-
    • 7-Isopropyl-5-methylbicyclo(2.2.2)oct-5-ene-2-carbonitrile
    • 7-isopropyl-5-methylbicyclo[2.2.2]oct-5-ene-2-carbonitrile
    • DTXSID80867572
    • 2-Methyl-5-isopropylbicyclo(2.2.2)oct-2-ene-8-nitrile
    • Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, 5-methyl-7-(1-methylethyl)-
    • 5-methyl-7-propan-2-ylbicyclo[2.2.2]oct-5-ene-2-carbonitrile
    • SCHEMBL7950438
    • DTXCID50815747
    • ZKFIXNXVHDGDTA-UHFFFAOYSA-N
    • NS00012746
    • 269-744-3

  • Applications

    Bicyclo[2.2.2]oct-5-ene-2-carbonitrile, 5-methyl-7-(1-methylethyl)- (CAS 68311-05-7) is primarily used as a synthetic building block and intermediate in organic synthesis. It is commonly evaluated as a precursor for pharmaceutical and agrochemical development and provides a rigid nitrile-containing scaffold for the construction of heterocycles and for SAR studies. In the materials arena, the compound may serve as a functionalizable building block for specialty polymers and crosslinking formulations, including coatings and adhesives, where the nitrile group enables further transformations or crosslinking. It may also be used in advanced polymer and plastics formulations after suitable functionalization, acting as a nitrile-containing monomer or comonomer in niche systems. Finally, because of its well-defined bicyclic structure, it is often considered as an intermediate for route development and scale-up in synthetic chemistry, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 40.09
    methanol 37.23
    isopropanol 34.86
    water 0.67
    ethyl acetate 122.01
    n-propanol 43.46
    acetone 163.34
    n-butanol 39.61
    acetonitrile 110.58
    DMF 226.93
    toluene 111.14
    isobutanol 34.32
    1,4-dioxane 224.6
    methyl acetate 138.07
    THF 318.51
    2-butanone 143.34
    n-pentanol 25.2
    sec-butanol 27.19
    n-hexane 3.84
    ethylene glycol 20.8
    NMP 243.19
    cyclohexane 16.99
    DMSO 164.95
    n-butyl acetate 111.86
    n-octanol 35.41
    chloroform 457.67
    n-propyl acetate 70.41
    acetic acid 81.51
    dichloromethane 445.37
    cyclohexanone 263.04
    propylene glycol 21.64
    isopropyl acetate 74.04
    DMAc 149.76
    2-ethoxyethanol 44.58
    isopentanol 34.69
    n-heptane 8.45
    ethyl formate 104.26
    1,2-dichloroethane 224.72
    n-hexanol 55.67
    2-methoxyethanol 80.3
    isobutyl acetate 53.2
    tetrachloromethane 69.93
    n-pentyl acetate 69.89
    transcutol 203.8
    n-heptanol 35.25
    ethylbenzene 46.85
    MIBK 65.81
    2-propoxyethanol 97.51
    tert-butanol 39.28
    MTBE 32.84
    2-butoxyethanol 65.27
    propionic acid 72.71
    o-xylene 65.95
    formic acid 27.5
    diethyl ether 52.15
    m-xylene 72.89
    p-xylene 66.03
    chlorobenzene 169.11
    dimethyl carbonate 74.36
    n-octane 4.43
    formamide 51.76
    cyclopentanone 360.2
    2-pentanone 103.39
    anisole 83.86
    cyclopentyl methyl ether 101.76
    gamma-butyrolactone 368.13
    1-methoxy-2-propanol 70.01
    pyridine 254.5
    3-pentanone 93.2
    furfural 298.15
    n-dodecane 4.95
    diethylene glycol 78.58
    diisopropyl ether 20.37
    tert-amyl alcohol 25.69
    acetylacetone 181.09
    n-hexadecane 5.83
    acetophenone 98.18
    methyl propionate 104.49
    isopentyl acetate 95.14
    trichloroethylene 463.09
    n-nonanol 33.69
    cyclohexanol 55.13
    benzyl alcohol 71.22
    2-ethylhexanol 41.83
    isooctanol 30.29
    dipropyl ether 50.17
    1,2-dichlorobenzene 157.32
    ethyl lactate 47.87
    propylene carbonate 216.7
    n-methylformamide 103.27
    2-pentanol 23.15
    n-pentane 4.73
    1-propoxy-2-propanol 77.62
    1-methoxy-2-propyl acetate 120.78
    2-(2-methoxypropoxy) propanol 76.73
    mesitylene 45.11
    ε-caprolactone 193.36
    p-cymene 45.09
    epichlorohydrin 302.86
    1,1,1-trichloroethane 212.26
    2-aminoethanol 30.51
    morpholine-4-carbaldehyde 223.47
    sulfolane 314.31
    2,2,4-trimethylpentane 3.38
    2-methyltetrahydrofuran 160.92
    n-hexyl acetate 93.0
    isooctane 3.4
    2-(2-butoxyethoxy)ethanol 92.6
    sec-butyl acetate 49.97
    tert-butyl acetate 73.94
    decalin 10.1
    glycerin 35.24
    diglyme 176.33
    acrylic acid 85.42
    isopropyl myristate 44.55
    n-butyric acid 97.73
    acetyl acetate 117.83
    di(2-ethylhexyl) phthalate 56.43
    ethyl propionate 66.63
    nitromethane 202.51
    1,2-diethoxyethane 80.98
    benzonitrile 140.92
    trioctyl phosphate 41.3
    1-bromopropane 91.76
    gamma-valerolactone 358.34
    n-decanol 27.01
    triethyl phosphate 50.61
    4-methyl-2-pentanol 20.01
    propionitrile 89.66
    vinylene carbonate 234.67
    1,1,2-trichlorotrifluoroethane 164.02
    DMS 114.14
    cumene 34.72
    2-octanol 23.77
    2-hexanone 68.55
    octyl acetate 55.36
    limonene 55.02
    1,2-dimethoxyethane 97.99
    ethyl orthosilicate 44.67
    tributyl phosphate 46.89
    diacetone alcohol 77.92
    N,N-dimethylaniline 56.72
    acrylonitrile 129.03
    aniline 93.75
    1,3-propanediol 41.41
    bromobenzene 185.76
    dibromomethane 247.01
    1,1,2,2-tetrachloroethane 290.74
    2-methyl-cyclohexyl acetate 82.51
    tetrabutyl urea 56.89
    diisobutyl methanol 30.55
    2-phenylethanol 89.95
    styrene 57.42
    dioctyl adipate 66.8
    dimethyl sulfate 110.88
    ethyl butyrate 84.3
    methyl lactate 61.52
    butyl lactate 64.76
    diethyl carbonate 69.57
    propanediol butyl ether 63.93
    triethyl orthoformate 58.72
    p-tert-butyltoluene 41.24
    methyl 4-tert-butylbenzoate 93.94
    morpholine 182.08
    tert-butylamine 24.04
    n-dodecanol 22.34
    dimethoxymethane 117.27
    ethylene carbonate 179.25
    cyrene 95.1
    2-ethoxyethyl acetate 108.14
    2-ethylhexyl acetate 81.44
    1,2,4-trichlorobenzene 179.21
    4-methylpyridine 202.19
    dibutyl ether 38.68
    2,6-dimethyl-4-heptanol 30.55
    DEF 98.61
    dimethyl isosorbide 172.22
    tetrachloroethylene 181.74
    eugenol 91.44
    triacetin 113.52
    span 80 76.25
    1,4-butanediol 19.83
    1,1-dichloroethane 199.54
    2-methyl-1-pentanol 26.84
    methyl formate 110.26
    2-methyl-1-butanol 30.27
    n-decane 7.26
    butyronitrile 87.45
    3,7-dimethyl-1-octanol 35.72
    1-chlorooctane 30.76
    1-chlorotetradecane 15.69
    n-nonane 6.27
    undecane 5.8
    tert-butylcyclohexane 8.36
    cyclooctane 6.62
    cyclopentanol 71.71
    tetrahydropyran 173.84
    tert-amyl methyl ether 26.19
    2,5,8-trioxanonane 131.19
    1-hexene 17.31
    2-isopropoxyethanol 38.98
    2,2,2-trifluoroethanol 51.85
    methyl butyrate 85.41

    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