Ethyl 5-norbornene-2-carboxylate

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  • Identifiers

    CAS number
    10138-32-6

    Molecular formula
    C10H14O2

    SMILES
    CCOC(=O)C1CC2CC1C=C2

  • Odor profile

    Fragrance
    Fruity 92.14%
    Green 80.63%
    Floral 56.75%
    Sweet 43.01%
    Woody 42.94%
    Herbal 39.59%
    Jasmin 36.41%
    Fresh 32.03%
    Apple 31.13%
    Balsamic 29.86%

     

    Flavor
    Bitter 47.69%
    Fruity 36.27%
    Fruit 25.7%
    Plant 20.48%
    Cedarleaf 20.23%
    Tarragon 20.19%
    Floral 19.96%
    Alkaline 19.95%
    Shrimp 19.82%
    Old wood 19.82%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    7.11 (neutral)

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    208°C

    Flash point

    • 94.02 ˚C est.

    Solubility expt.

    • very slightly soluble
    • Soluble (in ethanol)

  • Synonyms

    • 10138-32-6
    • ETHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE
    • Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, ethyl ester
    • Ethyl 5-norbornene-2-carboxylate
    • 5-Norbornene-2-carboxylic acid, ethyl ester
    • NSC 26489
    • QEA96R4A1Z
    • BICYCLO(2.2.1)HEPT-5-ENE-2-CARBOXYLIC ACID, ETHYL ESTER
    • DTXSID30884451
    • NSC-26489
    • NSC-62714
    • WLN: L55 A CUTJ FVO2
    • ethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate
    • UNII-QEA96R4A1Z
    • ETHYL BICYCLO(2.2.1)HEPT-5-ENE-2-CARBOXYLATE
    • NSC26489
    • 2,5-Endomethylene-3-cyclohexene carboxylic acid, ethyl ester
    • 5-ethoxycarbonylnorbornene
    • NCIOpen2_000131
    • 2-ethoxycarbonyl-5-norbornene
    • SCHEMBL200507
    • FEMA NO. 4790
    • FCCGTJAGEHZPBF-UHFFFAOYSA-N
    • DTXCID701023892
    • NSC62714
    • AKOS015917768
    • AC-4862
    • AS-75467
    • DB-058601
    • 5-NORBORNENECARBOXYLIC ACID ETHYL ESTER
    • E77868

  • Applications

    Ethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (CAS 10138-32-6) is a high-strain norbornyl ester that serves as a versatile building block in advanced organic synthesis: its bicyclic framework undergoes ring-opening additions, hydrogen abstractions and Baeyer-Villiger rearrangements, while the ethyl ester handle can be smoothly hydrolyzed, amidated or trans-esterified to give functional acids, amides and salts; consequently the molecule is employed as a monomer or pre-monomer for Ring-Opening Metathesis Polymerization, producing high-modulus, heat-resistant polynorbornene materials for specialty coatings, adhesives and epoxy curing systems; in pharmaceutical research its rigid non-aromatic scaffold orients pharmacophores for enzyme inhibitors, antiviral leads and selective cytotoxins, and also serves as a precursor to chiral resolving auxiliaries; in agrochemistry it is incorporated into the synthesis of pyridazinone pesticides and plant growth regulators; additional studies explore its use as a balsamic-woody fragrance ingredient, a corrosion-control additive, and a mechanistic probe in Diels-Alder chemistry, highlighting the broad applicability of this compact yet reactive compound.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 601.52
    methanol 719.06
    isopropanol 561.41
    water 8.62
    ethyl acetate 291.2
    n-propanol 499.48
    acetone 447.48
    n-butanol 476.9
    acetonitrile 463.56
    DMF 638.91
    toluene 261.61
    isobutanol 441.14
    1,4-dioxane 602.2
    methyl acetate 336.66
    THF 672.69
    2-butanone 389.03
    n-pentanol 376.14
    sec-butanol 474.55
    n-hexane 42.42
    ethylene glycol 179.52
    NMP 502.43
    cyclohexane 73.36
    DMSO 454.97
    n-butyl acetate 276.46
    n-octanol 268.48
    chloroform 2149.07
    n-propyl acetate 249.95
    acetic acid 634.98
    dichloromethane 1468.13
    cyclohexanone 548.1
    propylene glycol 268.06
    isopropyl acetate 215.21
    DMAc 437.82
    2-ethoxyethanol 386.77
    isopentanol 425.16
    n-heptane 30.5
    ethyl formate 317.98
    1,2-dichloroethane 595.97
    n-hexanol 344.12
    2-methoxyethanol 583.34
    isobutyl acetate 183.55
    tetrachloromethane 235.16
    n-pentyl acetate 215.24
    transcutol 976.46
    n-heptanol 210.4
    ethylbenzene 185.07
    MIBK 241.2
    2-propoxyethanol 456.38
    tert-butanol 495.2
    MTBE 301.2
    2-butoxyethanol 328.76
    propionic acid 413.24
    o-xylene 186.95
    formic acid 244.09
    diethyl ether 250.68
    m-xylene 204.79
    p-xylene 255.6
    chlorobenzene 463.06
    dimethyl carbonate 165.35
    n-octane 23.03
    formamide 302.38
    cyclopentanone 551.33
    2-pentanone 311.66
    anisole 335.04
    cyclopentyl methyl ether 297.23
    gamma-butyrolactone 625.2
    1-methoxy-2-propanol 444.08
    pyridine 658.77
    3-pentanone 222.77
    furfural 693.14
    n-dodecane 28.5
    diethylene glycol 405.19
    diisopropyl ether 105.0
    tert-amyl alcohol 392.55
    acetylacetone 332.83
    n-hexadecane 31.35
    acetophenone 324.5
    methyl propionate 248.11
    isopentyl acetate 270.46
    trichloroethylene 1283.99
    n-nonanol 215.23
    cyclohexanol 400.54
    benzyl alcohol 342.63
    2-ethylhexanol 193.2
    isooctanol 180.42
    dipropyl ether 139.64
    1,2-dichlorobenzene 416.56
    ethyl lactate 189.16
    propylene carbonate 451.75
    n-methylformamide 383.3
    2-pentanol 333.45
    n-pentane 48.25
    1-propoxy-2-propanol 315.73
    1-methoxy-2-propyl acetate 257.83
    2-(2-methoxypropoxy) propanol 310.1
    mesitylene 135.62
    ε-caprolactone 473.34
    p-cymene 117.3
    epichlorohydrin 683.09
    1,1,1-trichloroethane 627.83
    2-aminoethanol 347.04
    morpholine-4-carbaldehyde 545.86
    sulfolane 644.04
    2,2,4-trimethylpentane 37.6
    2-methyltetrahydrofuran 470.23
    n-hexyl acetate 367.81
    isooctane 36.07
    2-(2-butoxyethoxy)ethanol 419.25
    sec-butyl acetate 178.74
    tert-butyl acetate 230.66
    decalin 53.88
    glycerin 328.77
    diglyme 601.8
    acrylic acid 422.84
    isopropyl myristate 144.89
    n-butyric acid 510.4
    acetyl acetate 236.59
    di(2-ethylhexyl) phthalate 162.55
    ethyl propionate 217.49
    nitromethane 636.98
    1,2-diethoxyethane 275.75
    benzonitrile 508.3
    trioctyl phosphate 117.18
    1-bromopropane 377.31
    gamma-valerolactone 659.55
    n-decanol 163.19
    triethyl phosphate 122.64
    4-methyl-2-pentanol 216.46
    propionitrile 408.83
    vinylene carbonate 493.35
    1,1,2-trichlorotrifluoroethane 600.0
    DMS 253.66
    cumene 147.03
    2-octanol 168.76
    2-hexanone 262.32
    octyl acetate 186.64
    limonene 141.22
    1,2-dimethoxyethane 509.64
    ethyl orthosilicate 117.03
    tributyl phosphate 132.18
    diacetone alcohol 296.85
    N,N-dimethylaniline 229.44
    acrylonitrile 510.07
    aniline 355.79
    1,3-propanediol 437.9
    bromobenzene 483.3
    dibromomethane 974.33
    1,1,2,2-tetrachloroethane 1044.22
    2-methyl-cyclohexyl acetate 194.96
    tetrabutyl urea 162.87
    diisobutyl methanol 125.22
    2-phenylethanol 306.76
    styrene 236.73
    dioctyl adipate 194.46
    dimethyl sulfate 233.95
    ethyl butyrate 204.72
    methyl lactate 220.6
    butyl lactate 210.33
    diethyl carbonate 175.23
    propanediol butyl ether 387.38
    triethyl orthoformate 155.22
    p-tert-butyltoluene 108.06
    methyl 4-tert-butylbenzoate 287.43
    morpholine 607.85
    tert-butylamine 327.36
    n-dodecanol 127.84
    dimethoxymethane 336.09
    ethylene carbonate 379.79
    cyrene 276.73
    2-ethoxyethyl acetate 257.77
    2-ethylhexyl acetate 200.75
    1,2,4-trichlorobenzene 473.12
    4-methylpyridine 579.89
    dibutyl ether 194.12
    2,6-dimethyl-4-heptanol 125.22
    DEF 303.0
    dimethyl isosorbide 392.91
    tetrachloroethylene 671.9
    eugenol 306.77
    triacetin 309.28
    span 80 284.87
    1,4-butanediol 246.81
    1,1-dichloroethane 750.6
    2-methyl-1-pentanol 339.79
    methyl formate 324.24
    2-methyl-1-butanol 396.07
    n-decane 42.71
    butyronitrile 456.24
    3,7-dimethyl-1-octanol 229.56
    1-chlorooctane 165.86
    1-chlorotetradecane 71.03
    n-nonane 40.76
    undecane 33.8
    tert-butylcyclohexane 51.25
    cyclooctane 28.14
    cyclopentanol 421.81
    tetrahydropyran 488.34
    tert-amyl methyl ether 206.7
    2,5,8-trioxanonane 435.46
    1-hexene 160.74
    2-isopropoxyethanol 287.16
    2,2,2-trifluoroethanol 266.86
    methyl butyrate 288.94

    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