5-Methylenenorbornene

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  • Identifiers

    CAS number
    694-91-7

    Molecular formula
    C8H10

    SMILES
    C=C1CC2CC1C=C2

    Safety labels

    Flammable
    Flammable

  • Odor profile

    Fragrance
    Green 57.71%
    Fruity 55.11%
    Woody 41.2%
    Herbal 39.47%
    Fresh 38.64%
    Spicy 37.0%
    Citrus 36.58%
    Sweet 29.46%
    Floral 27.88%
    Oily 27.71%

     

    Flavor
    Bitter 26.35%
    Spice 25.12%
    Animal 22.55%
    Shrimp 22.24%
    Terpentine 21.55%
    Alkaline 21.52%
    Mint 20.79%
    Herbal 20.4%
    Nitrile 20.18%
    Citric 19.84%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    9.57 (weak base)

    Molecular weight
    106.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    121°C

    Flash point

    • 10.13 ˚C est.

  • Synonyms

    • 5-Methylene-2-norbornene
    • 694-91-7
    • 5-Methylenenorbornene
    • 2-Norbornene, 5-methylene-
    • Bicyclo[2.2.1]hept-2-ene, 5-methylene-
    • 5-Methylenebicyclo[2.2.1]hept-2-ene
    • DTXSID70862374
    • NSC-91504
    • 5-Methylenebicyclo(2.2.1)hept-2-ene
    • Bicyclo(2.2.1)hept-2-ene, 5-methylene-
    • NSC 91504
    • 5Methylenenorbornene
    • 2-METHYLENEBICYCLO(2.2.1)HEPT-5-ENE
    • RefChem:537253
    • BICYCLO(2.2.1)HEPT-2-ENE, 5-METHYLENE-, (1R,4R)-REL-
    • DTXCID40811152
    • Bicyclo(2.2.1)hept2ene, 5methylene
    • 684-694-6
    • EVM7GXX83N
    • 2-Methylene-5-norbornene
    • 5-methylidenebicyclo[2.2.1]hept-2-ene
    • 5-Methylene-2-norbornylene
    • 5-Methylenebicyclo[2.2.1]-2-heptene
    • Bicyclo[2.2.1]hept-2-ene,5-methylene-
    • (1R,4R)-5-Methylenebicyclo[2.2.1]hept-2-ene
    • NSC91504
    • 5-methylene -2-norbornene
    • SCHEMBL21981
    • SCHEMBL9250301
    • SCHEMBL9250305
    • AC9080
    • Q67879636
    • 694-91-7

  • Applications

    5-Methylenenorbornene (CAS 694-91-7) is a strained cyclic olefin commonly used as a ROMP monomer to access polynorbornene-type polymers with tailored properties for high-performance coatings and adhesives. It also serves as a building block in specialty resins and functional polymers, enabling targeted material design. The exocyclic methylene group provides a handle for post-polymerization modification and potential crosslinking in polymer networks, expanding its use in coating formulations and adhesive systems. As an intermediate in organic synthesis, it supports the development of advanced materials and functional monomers. In research and development, it is frequently examined to explore structure–property relationships in ROMP-derived polymers and networks, informing the design of materials for demanding applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1468.96
    methanol 1232.1
    isopropanol 1061.83
    water 3.42
    ethyl acetate 2093.93
    n-propanol 1287.59
    acetone 1184.17
    n-butanol 1237.12
    acetonitrile 1149.03
    DMF 732.64
    toluene 894.89
    isobutanol 767.05
    1,4-dioxane 2348.78
    methyl acetate 1332.18
    THF 2223.71
    2-butanone 1302.07
    n-pentanol 753.12
    sec-butanol 987.73
    n-hexane 273.43
    ethylene glycol 246.54
    NMP 594.7
    cyclohexane 336.8
    DMSO 591.61
    n-butyl acetate 1380.77
    n-octanol 408.75
    chloroform 2689.88
    n-propyl acetate 708.42
    acetic acid 879.88
    dichloromethane 1834.03
    cyclohexanone 1088.85
    propylene glycol 428.6
    isopropyl acetate 1113.2
    DMAc 780.7
    2-ethoxyethanol 956.06
    isopentanol 925.21
    n-heptane 272.19
    ethyl formate 729.26
    1,2-dichloroethane 935.85
    n-hexanol 1055.81
    2-methoxyethanol 1371.51
    isobutyl acetate 456.63
    tetrachloromethane 592.78
    n-pentyl acetate 540.89
    transcutol 3344.18
    n-heptanol 420.05
    ethylbenzene 280.59
    MIBK 716.74
    2-propoxyethanol 1556.12
    tert-butanol 1003.81
    MTBE 1393.06
    2-butoxyethanol 740.11
    propionic acid 849.0
    o-xylene 388.58
    formic acid 318.56
    diethyl ether 2113.0
    m-xylene 567.53
    p-xylene 294.27
    chlorobenzene 655.14
    dimethyl carbonate 447.81
    n-octane 88.37
    formamide 476.93
    cyclopentanone 1083.17
    2-pentanone 1262.6
    anisole 652.29
    cyclopentyl methyl ether 1169.09
    gamma-butyrolactone 1123.61
    1-methoxy-2-propanol 1285.21
    pyridine 1492.74
    3-pentanone 1027.71
    furfural 893.32
    n-dodecane 59.88
    diethylene glycol 931.22
    diisopropyl ether 695.97
    tert-amyl alcohol 790.44
    acetylacetone 1004.41
    n-hexadecane 66.5
    acetophenone 419.14
    methyl propionate 1163.7
    isopentyl acetate 940.66
    trichloroethylene 1631.07
    n-nonanol 380.51
    cyclohexanol 740.12
    benzyl alcohol 429.18
    2-ethylhexanol 627.7
    isooctanol 324.7
    dipropyl ether 1112.1
    1,2-dichlorobenzene 473.35
    ethyl lactate 273.28
    propylene carbonate 669.52
    n-methylformamide 647.02
    2-pentanol 937.1
    n-pentane 356.58
    1-propoxy-2-propanol 1328.36
    1-methoxy-2-propyl acetate 1159.93
    2-(2-methoxypropoxy) propanol 611.81
    mesitylene 340.81
    ε-caprolactone 1064.07
    p-cymene 246.08
    epichlorohydrin 1322.38
    1,1,1-trichloroethane 1137.3
    2-aminoethanol 589.74
    morpholine-4-carbaldehyde 972.13
    sulfolane 596.47
    2,2,4-trimethylpentane 146.41
    2-methyltetrahydrofuran 1600.32
    n-hexyl acetate 684.41
    isooctane 157.62
    2-(2-butoxyethoxy)ethanol 1015.58
    sec-butyl acetate 536.91
    tert-butyl acetate 897.47
    decalin 134.97
    glycerin 473.06
    diglyme 1574.18
    acrylic acid 564.76
    isopropyl myristate 266.31
    n-butyric acid 1334.58
    acetyl acetate 1022.0
    di(2-ethylhexyl) phthalate 202.45
    ethyl propionate 657.66
    nitromethane 1105.49
    1,2-diethoxyethane 1715.02
    benzonitrile 571.03
    trioctyl phosphate 140.38
    1-bromopropane 1056.01
    gamma-valerolactone 1292.15
    n-decanol 281.46
    triethyl phosphate 230.09
    4-methyl-2-pentanol 548.16
    propionitrile 1089.44
    vinylene carbonate 676.11
    1,1,2-trichlorotrifluoroethane 742.58
    DMS 494.28
    cumene 195.34
    2-octanol 273.82
    2-hexanone 675.09
    octyl acetate 320.83
    limonene 377.87
    1,2-dimethoxyethane 1081.47
    ethyl orthosilicate 262.69
    tributyl phosphate 192.67
    diacetone alcohol 709.67
    N,N-dimethylaniline 339.05
    acrylonitrile 950.28
    aniline 874.87
    1,3-propanediol 850.34
    bromobenzene 721.16
    dibromomethane 1358.39
    1,1,2,2-tetrachloroethane 1113.57
    2-methyl-cyclohexyl acetate 385.67
    tetrabutyl urea 212.61
    diisobutyl methanol 368.68
    2-phenylethanol 599.92
    styrene 370.86
    dioctyl adipate 297.74
    dimethyl sulfate 346.13
    ethyl butyrate 778.66
    methyl lactate 418.71
    butyl lactate 333.25
    diethyl carbonate 438.01
    propanediol butyl ether 532.77
    triethyl orthoformate 546.81
    p-tert-butyltoluene 259.24
    methyl 4-tert-butylbenzoate 386.71
    morpholine 2286.1
    tert-butylamine 753.06
    n-dodecanol 218.72
    dimethoxymethane 1099.8
    ethylene carbonate 662.5
    cyrene 312.59
    2-ethoxyethyl acetate 896.51
    2-ethylhexyl acetate 764.23
    1,2,4-trichlorobenzene 530.7
    4-methylpyridine 1139.12
    dibutyl ether 690.2
    2,6-dimethyl-4-heptanol 368.68
    DEF 1060.49
    dimethyl isosorbide 762.95
    tetrachloroethylene 856.58
    eugenol 362.49
    triacetin 505.41
    span 80 490.39
    1,4-butanediol 321.76
    1,1-dichloroethane 1251.26
    2-methyl-1-pentanol 599.01
    methyl formate 409.56
    2-methyl-1-butanol 844.88
    n-decane 104.25
    butyronitrile 1148.62
    3,7-dimethyl-1-octanol 476.98
    1-chlorooctane 275.06
    1-chlorotetradecane 125.96
    n-nonane 107.53
    undecane 76.16
    tert-butylcyclohexane 140.76
    cyclooctane 164.12
    cyclopentanol 646.48
    tetrahydropyran 1969.89
    tert-amyl methyl ether 909.24
    2,5,8-trioxanonane 1017.07
    1-hexene 595.42
    2-isopropoxyethanol 746.79
    2,2,2-trifluoroethanol 330.81
    methyl butyrate 652.06

    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