(5E)-5-Ethylidenebicyclo[2.2.1]hept-2-ene

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  • Identifiers

    CAS number
    16219-75-3

    Molecular formula
    C9H12

    SMILES
    CC=C1CC2CC1C=C2

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Woody 56.3%
    Herbal 53.32%
    Spicy 52.86%
    Fruity 50.34%
    Citrus 46.69%
    Fresh 40.37%
    Green 39.61%
    Sweet 39.04%
    Oily 32.03%
    Floral 29.27%

     

    Flavor
    Spice 39.83%
    Woody 34.49%
    Wood 34.22%
    Herbal 33.86%
    Sweet 24.07%
    Herb 23.77%
    Spicy 23.09%
    Mint 22.6%
    Terpentine 22.26%
    Balsamic 21.59%

     

    Odor impact est.
    High

    Odor threshold

    • Odor Threshold Low: 0.07 [mmHg]. Odor threshold (detection or recognition not specified), from CHEMINFO
    • An odor threshold of 0.014 ppm has been reported.

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    9.95 (weak base)

    Molecular weight
    120.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -112 °F (USCG, 1999)
    • FP: -80 °C
    • -80 °C
    • -112 °F

    Boiling point

    • 297.7 °F at 760 mmHg (USCG, 1999)
    • 67 °C @ 50 MM HG
    • 148 °C
    • 298 °F

    Flash point

    • 29.58 ˚C est.
    • 79 °F (NTP, 1992)
    • 38 °C
    • 38.33 °C, open cup
    • 38 °C o.c.
    • 79 °F
    • (oc) 101 °F

    Solubility expt.

    • less than 1 mg/mL at 64 °F (NTP, 1992)
    • Solubility in water: none

  • Synonyms

    • 16219-75-3
    • 5-ETHYLIDENE-2-NORBORNENE
    • (5E)-5-Ethylidenebicyclo[2.2.1]hept-2-ene
    • Ethylidene-2-norbornene
    • ethylidene-norbornene
    • DTXSID1025306
    • ENB
    • 5-ethylidene 2-norbornene
    • CHEMBL3188004
    • AKOS028109999
    • FE34580
    • 5-ethylidenebicy-clo[2.2.1]hept-2-ene
    • 5-Ethylidene-2-norbornene, sum of endo and exo, stabilizer with BHT

  • Applications

    (5E)-5-Ethylidenebicyclo[2.2.1]hept-2-ene (CAS 16219-75-3) is predominantly used as a non-conjugated diene monomer in EPDM rubber production, providing cure sites for sulfur- or peroxide-based vulcanization and improving heat, oil, and weather resistance. It serves as a reactive monomer in EPDM formulations for automotive seals, hoses, and gaskets. It is also employed as a feedstock for ROMP-based polymerization to produce specialty poly(norbornene) and functionalized polymers used in coatings and adhesives. Additionally, ENB acts as a precursor for synthesizing functional norbornene derivatives used as crosslinkers or building blocks in advanced polymer systems. In some contexts it is used as an intermediate in chemical synthesis and formulation strategies requiring controlled unsaturation, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 546.11
    methanol 409.0
    isopropanol 474.69
    water 1.05
    ethyl acetate 932.52
    n-propanol 526.92
    acetone 823.49
    n-butanol 556.5
    acetonitrile 686.57
    DMF 521.78
    toluene 809.88
    isobutanol 414.21
    1,4-dioxane 1533.24
    methyl acetate 717.54
    THF 1749.34
    2-butanone 788.75
    n-pentanol 402.61
    sec-butanol 440.01
    n-hexane 316.14
    ethylene glycol 110.35
    NMP 585.86
    cyclohexane 388.96
    DMSO 522.24
    n-butyl acetate 829.54
    n-octanol 347.24
    chloroform 1706.47
    n-propyl acetate 456.74
    acetic acid 349.48
    dichloromethane 1376.71
    cyclohexanone 980.8
    propylene glycol 180.3
    isopropyl acetate 622.7
    DMAc 487.94
    2-ethoxyethanol 474.21
    isopentanol 521.71
    n-heptane 299.93
    ethyl formate 347.57
    1,2-dichloroethane 836.29
    n-hexanol 854.82
    2-methoxyethanol 624.93
    isobutyl acetate 368.83
    tetrachloromethane 452.97
    n-pentyl acetate 404.27
    transcutol 1733.66
    n-heptanol 355.3
    ethylbenzene 333.5
    MIBK 575.66
    2-propoxyethanol 1082.65
    tert-butanol 583.09
    MTBE 792.44
    2-butoxyethanol 511.43
    propionic acid 346.72
    o-xylene 400.1
    formic acid 92.54
    diethyl ether 1122.08
    m-xylene 538.48
    p-xylene 354.18
    chlorobenzene 643.64
    dimethyl carbonate 284.6
    n-octane 108.86
    formamide 133.1
    cyclopentanone 987.47
    2-pentanone 789.13
    anisole 587.01
    cyclopentyl methyl ether 1012.96
    gamma-butyrolactone 836.28
    1-methoxy-2-propanol 665.19
    pyridine 1001.85
    3-pentanone 680.35
    furfural 701.56
    n-dodecane 88.26
    diethylene glycol 534.59
    diisopropyl ether 467.23
    tert-amyl alcohol 440.94
    acetylacetone 733.32
    n-hexadecane 98.36
    acetophenone 403.55
    methyl propionate 618.81
    isopentyl acetate 713.47
    trichloroethylene 1223.7
    n-nonanol 321.21
    cyclohexanol 532.55
    benzyl alcohol 346.72
    2-ethylhexanol 541.8
    isooctanol 289.98
    dipropyl ether 812.79
    1,2-dichlorobenzene 509.39
    ethyl lactate 195.53
    propylene carbonate 489.73
    n-methylformamide 280.26
    2-pentanol 456.28
    n-pentane 301.58
    1-propoxy-2-propanol 799.27
    1-methoxy-2-propyl acetate 737.76
    2-(2-methoxypropoxy) propanol 483.25
    mesitylene 369.13
    ε-caprolactone 783.83
    p-cymene 265.12
    epichlorohydrin 1051.29
    1,1,1-trichloroethane 976.47
    2-aminoethanol 215.4
    morpholine-4-carbaldehyde 813.74
    sulfolane 732.6
    2,2,4-trimethylpentane 141.2
    2-methyltetrahydrofuran 1283.63
    n-hexyl acetate 619.43
    isooctane 157.43
    2-(2-butoxyethoxy)ethanol 669.87
    sec-butyl acetate 388.9
    tert-butyl acetate 643.06
    decalin 184.77
    glycerin 227.71
    diglyme 1147.66
    acrylic acid 261.21
    isopropyl myristate 285.09
    n-butyric acid 551.41
    acetyl acetate 539.38
    di(2-ethylhexyl) phthalate 209.86
    ethyl propionate 434.76
    nitromethane 558.65
    1,2-diethoxyethane 849.95
    benzonitrile 465.69
    trioctyl phosphate 166.99
    1-bromopropane 812.55
    gamma-valerolactone 1018.05
    n-decanol 259.85
    triethyl phosphate 219.45
    4-methyl-2-pentanol 337.49
    propionitrile 599.39
    vinylene carbonate 463.11
    1,1,2-trichlorotrifluoroethane 557.75
    DMS 426.37
    cumene 240.32
    2-octanol 233.53
    2-hexanone 524.07
    octyl acetate 335.25
    limonene 398.71
    1,2-dimethoxyethane 787.51
    ethyl orthosilicate 229.29
    tributyl phosphate 198.8
    diacetone alcohol 529.57
    N,N-dimethylaniline 358.46
    acrylonitrile 544.79
    aniline 600.91
    1,3-propanediol 329.1
    bromobenzene 788.27
    dibromomethane 1052.71
    1,1,2,2-tetrachloroethane 976.05
    2-methyl-cyclohexyl acetate 398.0
    tetrabutyl urea 229.73
    diisobutyl methanol 311.09
    2-phenylethanol 527.25
    styrene 412.28
    dioctyl adipate 306.62
    dimethyl sulfate 294.36
    ethyl butyrate 531.32
    methyl lactate 254.25
    butyl lactate 252.47
    diethyl carbonate 322.52
    propanediol butyl ether 367.71
    triethyl orthoformate 359.58
    p-tert-butyltoluene 273.79
    methyl 4-tert-butylbenzoate 386.17
    morpholine 1282.71
    tert-butylamine 479.7
    n-dodecanol 214.51
    dimethoxymethane 711.42
    ethylene carbonate 438.01
    cyrene 316.19
    2-ethoxyethyl acetate 551.41
    2-ethylhexyl acetate 583.62
    1,2,4-trichlorobenzene 586.47
    4-methylpyridine 895.38
    dibutyl ether 534.71
    2,6-dimethyl-4-heptanol 311.09
    DEF 649.29
    dimethyl isosorbide 671.43
    tetrachloroethylene 669.6
    eugenol 361.42
    triacetin 441.05
    span 80 398.49
    1,4-butanediol 152.19
    1,1-dichloroethane 982.29
    2-methyl-1-pentanol 381.09
    methyl formate 223.5
    2-methyl-1-butanol 462.08
    n-decane 132.88
    butyronitrile 623.61
    3,7-dimethyl-1-octanol 400.37
    1-chlorooctane 328.42
    1-chlorotetradecane 165.91
    n-nonane 138.35
    undecane 104.31
    tert-butylcyclohexane 178.54
    cyclooctane 206.23
    cyclopentanol 485.6
    tetrahydropyran 1362.5
    tert-amyl methyl ether 553.78
    2,5,8-trioxanonane 766.01
    1-hexene 560.47
    2-isopropoxyethanol 437.14
    2,2,2-trifluoroethanol 142.72
    methyl butyrate 463.17

    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