Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, 1-methyl-4-(1-methylethyl)-, methyl ester

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  • Identifiers

    CAS number
    67392-15-8

    Molecular formula
    C14H22O2

    SMILES
    CC(C)C12CCC(C=C1)(C(C2)C(=O)OC)C

  • Odor profile

    Fragrance
    Woody 81.71%
    Herbal 50.18%
    Spicy 44.48%
    Dry 43.67%
    Amber 43.24%
    Balsamic 42.67%
    Cedar 40.59%
    Fruity 40.1%
    Green 35.48%
    Pine 34.21%

     

    Flavor
    Woody 43.0%
    Herbal 38.31%
    Fruity 35.61%
    Green 30.14%
    Bitter 29.73%
    Fruit 28.2%
    Herb 26.78%
    Pine 26.1%
    Wood 25.74%
    Balsam 24.45%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    7.44 (neutral)

    Molecular weight
    222.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    254°C

    Flash point

    • 123.23 ˚C est.

  • Synonyms

    • 67392-15-8
    • Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, 1-methyl-4-(1-methylethyl)-, methyl ester
    • Bicyclo(2.2.2)oct-5-ene-2-carboxylic acid, 1-methyl-4-(1-methylethyl)-, methyl ester
    • Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, 1(or 4)-methyl-4(or 1)-(1-methylethyl)-, methyl ester
    • Methyl 4-isopropyl-1-methylbicyclo(2.2.2)oct-5-ene-2-carboxylate
    • Bicyclo(2.2.2)oct-5-ene-2-carboxylic acid, 1(or 4)-methyl-4(or 1)-(1-methylethyl)-, methyl ester
    • EINECS 266-678-7
    • SCHEMBL1491168
    • DTXSID20867273
    • NXAJZPARDMDLKH-UHFFFAOYSA-N
    • EINECS 273-453-7
    • Methyl 1-methyl-4-(1-methylethyl)bicyclo(2.2.2)oct-2-ene-6-carboxylate
    • NS00012913
    • Methyl 1-methyl-4-isopropylbicyclo(2.2.2)oct-5-enecarboxylate
    • 2-Bicyclo(2.2.2)octen-5(6)-carbomethoxy, 1-methyl-4-isopropyl-
    • Bicyclo(2.2.2)oct-5-enecarboxylic acid, 1-methyl-4-isopropyl-, methyl ester
    • Methyl 4(or 1)-isopropyl-1(or 4)-methylbicyclo(2.2.2)oct-5-ene-2-carboxylate
    • 68966-86-9

  • Applications

    Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid, 1-methyl-4-(1-methylethyl)-, methyl ester (CAS 67392-15-8) is primarily used as an organic synthesis intermediate to access bicyclic frameworks in medicinal chemistry and agrochemical research; it is also evaluated as a ROMP (ring-opening metathesis polymerization) monomer for the production of specialty polymers and high-performance coatings, where its rigid bicyclic skeleton and ester functionality enable tailoring of properties. In coatings, inks, and adhesives, it can serve as a reactive crosslinkable component to reinforce resin networks. In research settings, it can act as a building block for developing chiral ligands or catalysts for asymmetric synthesis. Additionally, it may be explored as a precursor to high-performance resins and functional polymers for advanced materials applications such as electronics or composites, subject to formulation constraints and regulatory considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 92.52
    methanol 89.23
    isopropanol 106.19
    water 0.79
    ethyl acetate 168.84
    n-propanol 104.99
    acetone 164.07
    n-butanol 92.22
    acetonitrile 129.14
    DMF 392.87
    toluene 266.57
    isobutanol 89.11
    1,4-dioxane 477.55
    methyl acetate 197.02
    THF 511.41
    2-butanone 194.41
    n-pentanol 51.37
    sec-butanol 80.06
    n-hexane 5.11
    ethylene glycol 24.14
    NMP 301.84
    cyclohexane 30.72
    DMSO 134.59
    n-butyl acetate 125.02
    n-octanol 47.01
    chloroform 861.14
    n-propyl acetate 89.41
    acetic acid 84.01
    dichloromethane 576.24
    cyclohexanone 332.12
    propylene glycol 36.28
    isopropyl acetate 119.33
    DMAc 282.91
    2-ethoxyethanol 75.25
    isopentanol 83.17
    n-heptane 5.93
    ethyl formate 106.11
    1,2-dichloroethane 301.26
    n-hexanol 102.35
    2-methoxyethanol 169.85
    isobutyl acetate 69.91
    tetrachloromethane 107.14
    n-pentyl acetate 85.11
    transcutol 293.58
    n-heptanol 58.25
    ethylbenzene 98.1
    MIBK 107.64
    2-propoxyethanol 171.67
    tert-butanol 125.89
    MTBE 109.96
    2-butoxyethanol 109.46
    propionic acid 91.72
    o-xylene 153.73
    formic acid 37.02
    diethyl ether 101.18
    m-xylene 176.67
    p-xylene 148.03
    chlorobenzene 271.74
    dimethyl carbonate 92.74
    n-octane 3.72
    formamide 79.31
    cyclopentanone 383.67
    2-pentanone 137.1
    anisole 162.23
    cyclopentyl methyl ether 182.26
    gamma-butyrolactone 372.74
    1-methoxy-2-propanol 158.27
    pyridine 380.02
    3-pentanone 132.86
    furfural 311.28
    n-dodecane 3.87
    diethylene glycol 113.0
    diisopropyl ether 39.9
    tert-amyl alcohol 86.05
    acetylacetone 180.93
    n-hexadecane 4.74
    acetophenone 145.14
    methyl propionate 155.84
    isopentyl acetate 129.99
    trichloroethylene 671.55
    n-nonanol 46.8
    cyclohexanol 129.0
    benzyl alcohol 121.06
    2-ethylhexanol 61.99
    isooctanol 48.7
    dipropyl ether 52.94
    1,2-dichlorobenzene 235.73
    ethyl lactate 55.33
    propylene carbonate 213.61
    n-methylformamide 140.35
    2-pentanol 60.28
    n-pentane 7.98
    1-propoxy-2-propanol 124.17
    1-methoxy-2-propyl acetate 167.75
    2-(2-methoxypropoxy) propanol 109.34
    mesitylene 101.36
    ε-caprolactone 257.02
    p-cymene 59.75
    epichlorohydrin 403.32
    1,1,1-trichloroethane 341.55
    2-aminoethanol 53.96
    morpholine-4-carbaldehyde 341.41
    sulfolane 288.56
    2,2,4-trimethylpentane 7.78
    2-methyltetrahydrofuran 284.57
    n-hexyl acetate 114.51
    isooctane 6.55
    2-(2-butoxyethoxy)ethanol 133.15
    sec-butyl acetate 76.88
    tert-butyl acetate 127.15
    decalin 17.33
    glycerin 56.03
    diglyme 248.76
    acrylic acid 88.92
    isopropyl myristate 48.95
    n-butyric acid 127.34
    acetyl acetate 132.48
    di(2-ethylhexyl) phthalate 61.12
    ethyl propionate 91.23
    nitromethane 179.25
    1,2-diethoxyethane 109.87
    benzonitrile 188.98
    trioctyl phosphate 41.94
    1-bromopropane 148.31
    gamma-valerolactone 442.07
    n-decanol 34.91
    triethyl phosphate 56.53
    4-methyl-2-pentanol 49.85
    propionitrile 141.31
    vinylene carbonate 229.8
    1,1,2-trichlorotrifluoroethane 220.21
    DMS 137.42
    cumene 64.76
    2-octanol 38.25
    2-hexanone 87.55
    octyl acetate 62.01
    limonene 70.31
    1,2-dimethoxyethane 179.15
    ethyl orthosilicate 55.09
    tributyl phosphate 47.08
    diacetone alcohol 134.97
    N,N-dimethylaniline 105.8
    acrylonitrile 181.57
    aniline 220.7
    1,3-propanediol 86.07
    bromobenzene 290.82
    dibromomethane 352.77
    1,1,2,2-tetrachloroethane 530.79
    2-methyl-cyclohexyl acetate 97.49
    tetrabutyl urea 59.96
    diisobutyl methanol 41.4
    2-phenylethanol 145.15
    styrene 115.66
    dioctyl adipate 70.94
    dimethyl sulfate 128.42
    ethyl butyrate 88.65
    methyl lactate 81.59
    butyl lactate 75.88
    diethyl carbonate 71.39
    propanediol butyl ether 85.72
    triethyl orthoformate 71.73
    p-tert-butyltoluene 59.44
    methyl 4-tert-butylbenzoate 133.15
    morpholine 439.99
    tert-butylamine 82.83
    n-dodecanol 26.54
    dimethoxymethane 208.6
    ethylene carbonate 186.69
    cyrene 124.49
    2-ethoxyethyl acetate 129.59
    2-ethylhexyl acetate 103.89
    1,2,4-trichlorobenzene 270.55
    4-methylpyridine 361.04
    dibutyl ether 43.23
    2,6-dimethyl-4-heptanol 41.4
    DEF 160.91
    dimethyl isosorbide 222.22
    tetrachloroethylene 317.89
    eugenol 124.49
    triacetin 126.56
    span 80 98.38
    1,4-butanediol 27.89
    1,1-dichloroethane 341.71
    2-methyl-1-pentanol 57.71
    methyl formate 113.85
    2-methyl-1-butanol 77.48
    n-decane 6.28
    butyronitrile 129.6
    3,7-dimethyl-1-octanol 52.43
    1-chlorooctane 33.82
    1-chlorotetradecane 15.31
    n-nonane 5.07
    undecane 4.8
    tert-butylcyclohexane 13.57
    cyclooctane 9.82
    cyclopentanol 138.25
    tetrahydropyran 349.25
    tert-amyl methyl ether 78.15
    2,5,8-trioxanonane 172.28
    1-hexene 25.26
    2-isopropoxyethanol 63.78
    2,2,2-trifluoroethanol 55.75
    methyl butyrate 110.17

    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