5-Norbornene-2-methylolacrylate

Overview IFRA Request a quote

  • Identifiers

    CAS number
    95-39-6

    Molecular formula
    C11H14O2

    SMILES
    C=CC(=O)OC[C@@H]1C[C@H]2C[C@@H]1C=C2

    Safety labels

  • Odor profile

    Fragrance
    Fruity 82.62%
    Green 73.46%
    Sweet 43.5%
    Woody 39.73%
    Herbal 38.65%
    Floral 35.12%
    Fresh 33.11%
    Balsamic 30.77%
    Pineapple 29.67%
    Tropical 27.57%

     

    Flavor
    Bitter 30.8%
    Odorless 24.41%
    Fruity 22.58%
    Orange flower 19.19%
    Ethyl benzoate 19.17%
    Nitrile 19.1%
    Shrimp 19.08%
    Lovage 19.05%
    Cotton candy 18.97%
    Fenugreek 18.91%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    7.12 (neutral)

    Molecular weight
    178.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point

    • 103-105 °C

    Flash point

    • 107.43 ˚C est.

    Solubility expt.

    • Sol in most organic solvents

  • Synonyms

    • Cyclol acrylate
    • 5-NORBORNENE-2-METHYLOLACRYLATE
    • UNII-YR5K75EW22
    • YR5K75EW22
    • HSDB 5290
    • Acrylic acid, 5-norbornen-2-ylmethyl ester
    • 5-Norbornene-2-methanol, acrylate
    • Bicyclo(2.2.1)hept-2-en-5-ylmethyl acrylate
    • EINECS 202-415-4
    • Bicyclo(2.2.1)hept-5-ene-2-methylol acrylate
    • Acrylic acid, 5-norbornen-2-methyl ester
    • AI3-26532
    • 2,5-Endomethylene-delta(3)-tetrahydrobenzyl acrylate
    • 2,5-endo-Methylene-delta(sup 3)-tetrahydrobenzyl acrylate
    • 5-NORBORNENE-2-METHYLOL ACRYLATE
    • 5-NORBORNENE-2-METHYLOLACRYLATE [HSDB]
    • 2,5-ENDOMETHYLENE-.DELTA.3-TETRAHYDROBENZYL ACRYLATE
    • RefChem:103292
    • 5Norbornene2methanol, acrylate
    • Acrylic acid, 5norbornen2methyl ester
    • Acrylic acid, 5norbornen2ylmethyl ester
    • Bicyclo(2.2.1)hept2en5ylmethyl acrylate
    • Bicyclo(2.2.1)hept5ene2methylol acrylate
    • (Bicyclo(2.2.1)hept5en2yl)methyl acrylate
    • 2,5Endomethylenedelta(3)tetrahydrobenzyl acrylate
    • 2,5endoMethylenedelta(sup 3)tetrahydrobenzyl acrylate
    • 2Propenoic acid, bicyclo(2.2.1)hept5en2ylmethyl ester
    • 2,5-ENDOMETHYLENE-DELTA3-TETRAHYDROBENZYL ACRYLATE
    • 2-Propenoic acid, bicyclo(2.2.1)hept-5-3N-2-ylmethyl ester.
    • 202-415-4
    • 95-39-6
    • SCHEMBL6520682
    • (Bicyclo(2.2.1)hept-5-en-2-yl)methyl acrylate
    • Q27294673
    • 95-39-6

  • Applications

    5-Norbornene-2-methylolacrylate is a functional monomer bearing a norbornene ring and an acrylate group, typically enabling radical polymerization or ROMP to produce polymers with rigid backbones and crosslinkable sites. The methylol group provides a handle for crosslinking and postfunctionalization with polyurethane or epoxy systems, enhancing hardness and chemical resistance of coatings and adhesives. Common applications include use as a reactive monomer in coatings and inks (UV-curable coatings and reactive inks), in specialty polymers and plastics (resins for industrial plastics), in adhesive formulations (crosslinked networks for high-strength bonds), and in electronics/optics-related resin formulations where stable, high-performance networks are beneficial. It is also evaluated as an intermediate in the synthesis of specialty polymers and networks with defined architectures, subject to formulation requirements and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 486.4
    methanol 508.09
    isopropanol 365.18
    water 0.63
    ethyl acetate 604.89
    n-propanol 337.73
    acetone 417.93
    n-butanol 375.29
    acetonitrile 334.31
    DMF 302.99
    toluene 254.68
    isobutanol 268.69
    1,4-dioxane 730.82
    methyl acetate 450.06
    THF 772.56
    2-butanone 444.13
    n-pentanol 241.25
    sec-butanol 304.62
    n-hexane 14.21
    ethylene glycol 62.51
    NMP 173.22
    cyclohexane 30.48
    DMSO 257.49
    n-butyl acetate 331.16
    n-octanol 90.97
    chloroform 1006.45
    n-propyl acetate 307.3
    acetic acid 366.01
    dichloromethane 791.59
    cyclohexanone 408.99
    propylene glycol 109.7
    isopropyl acetate 382.06
    DMAc 333.8
    2-ethoxyethanol 368.12
    isopentanol 382.81
    n-heptane 8.9
    ethyl formate 261.02
    1,2-dichloroethane 442.21
    n-hexanol 245.15
    2-methoxyethanol 561.66
    isobutyl acetate 220.68
    tetrachloromethane 72.73
    n-pentyl acetate 143.06
    transcutol 1617.49
    n-heptanol 95.23
    ethylbenzene 130.95
    MIBK 299.82
    2-propoxyethanol 447.81
    tert-butanol 384.3
    MTBE 389.32
    2-butoxyethanol 218.59
    propionic acid 230.65
    o-xylene 140.26
    formic acid 123.15
    diethyl ether 458.56
    m-xylene 187.52
    p-xylene 161.81
    chlorobenzene 267.51
    dimethyl carbonate 155.21
    n-octane 5.52
    formamide 220.59
    cyclopentanone 379.42
    2-pentanone 403.27
    anisole 306.28
    cyclopentyl methyl ether 315.02
    gamma-butyrolactone 403.94
    1-methoxy-2-propanol 521.15
    pyridine 482.73
    3-pentanone 255.16
    furfural 421.1
    n-dodecane 7.03
    diethylene glycol 333.93
    diisopropyl ether 142.09
    tert-amyl alcohol 298.95
    acetylacetone 419.59
    n-hexadecane 8.07
    acetophenone 273.83
    methyl propionate 337.88
    isopentyl acetate 322.64
    trichloroethylene 894.64
    n-nonanol 83.54
    cyclohexanol 239.46
    benzyl alcohol 237.91
    2-ethylhexanol 131.5
    isooctanol 93.3
    dipropyl ether 118.25
    1,2-dichlorobenzene 220.03
    ethyl lactate 138.16
    propylene carbonate 302.61
    n-methylformamide 209.11
    2-pentanol 286.58
    n-pentane 18.59
    1-propoxy-2-propanol 294.04
    1-methoxy-2-propyl acetate 379.39
    2-(2-methoxypropoxy) propanol 259.13
    mesitylene 111.13
    ε-caprolactone 379.61
    p-cymene 68.4
    epichlorohydrin 591.89
    1,1,1-trichloroethane 361.99
    2-aminoethanol 150.97
    morpholine-4-carbaldehyde 364.26
    sulfolane 275.2
    2,2,4-trimethylpentane 19.8
    2-methyltetrahydrofuran 524.11
    n-hexyl acetate 211.87
    isooctane 20.72
    2-(2-butoxyethoxy)ethanol 390.87
    sec-butyl acetate 255.15
    tert-butyl acetate 339.38
    decalin 24.19
    glycerin 146.07
    diglyme 595.48
    acrylic acid 181.33
    isopropyl myristate 82.31
    n-butyric acid 444.41
    acetyl acetate 321.14
    di(2-ethylhexyl) phthalate 91.06
    ethyl propionate 252.97
    nitromethane 503.53
    1,2-diethoxyethane 409.99
    benzonitrile 271.15
    trioctyl phosphate 57.87
    1-bromopropane 259.95
    gamma-valerolactone 520.87
    n-decanol 63.67
    triethyl phosphate 89.23
    4-methyl-2-pentanol 206.09
    propionitrile 272.31
    vinylene carbonate 294.76
    1,1,2-trichlorotrifluoroethane 361.58
    DMS 230.66
    cumene 93.71
    2-octanol 68.35
    2-hexanone 273.04
    octyl acetate 99.57
    limonene 85.74
    1,2-dimethoxyethane 521.74
    ethyl orthosilicate 88.06
    tributyl phosphate 80.01
    diacetone alcohol 352.6
    N,N-dimethylaniline 167.86
    acrylonitrile 298.94
    aniline 274.27
    1,3-propanediol 290.81
    bromobenzene 273.21
    dibromomethane 489.79
    1,1,2,2-tetrachloroethane 656.95
    2-methyl-cyclohexyl acetate 159.1
    tetrabutyl urea 86.82
    diisobutyl methanol 93.34
    2-phenylethanol 232.82
    styrene 166.0
    dioctyl adipate 117.74
    dimethyl sulfate 136.8
    ethyl butyrate 208.72
    methyl lactate 160.03
    butyl lactate 137.83
    diethyl carbonate 154.11
    propanediol butyl ether 220.89
    triethyl orthoformate 135.22
    p-tert-butyltoluene 63.26
    methyl 4-tert-butylbenzoate 173.38
    morpholine 707.05
    tert-butylamine 227.45
    n-dodecanol 49.79
    dimethoxymethane 392.12
    ethylene carbonate 257.89
    cyrene 184.87
    2-ethoxyethyl acetate 276.09
    2-ethylhexyl acetate 228.1
    1,2,4-trichlorobenzene 255.47
    4-methylpyridine 460.47
    dibutyl ether 123.27
    2,6-dimethyl-4-heptanol 93.34
    DEF 307.99
    dimethyl isosorbide 321.96
    tetrachloroethylene 381.11
    eugenol 188.8
    triacetin 237.26
    span 80 186.16
    1,4-butanediol 105.93
    1,1-dichloroethane 489.62
    2-methyl-1-pentanol 261.99
    methyl formate 161.36
    2-methyl-1-butanol 302.47
    n-decane 10.07
    butyronitrile 309.03
    3,7-dimethyl-1-octanol 123.44
    1-chlorooctane 54.91
    1-chlorotetradecane 24.59
    n-nonane 8.15
    undecane 8.16
    tert-butylcyclohexane 23.87
    cyclooctane 12.29
    cyclopentanol 198.0
    tetrahydropyran 605.83
    tert-amyl methyl ether 251.82
    2,5,8-trioxanonane 396.0
    1-hexene 94.99
    2-isopropoxyethanol 294.64
    2,2,2-trifluoroethanol 128.48
    methyl butyrate 325.47

    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