1,2-Epoxycyclopentane

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  • Identifiers

    CAS number
    285-67-6

    Molecular formula
    C5H8O

    SMILES
    C1C[C@@H]2[C@H](C1)O2

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 34.09%
    Woody 30.75%
    Floral 27.99%
    Animal 27.47%
    Fishy 25.87%
    Solvent 23.18%
    Fresh 22.88%
    Earthy 22.7%
    Mint 22.59%
    Ethereal 22.56%

     

    Flavor
    Bitter 31.5%
    Animal 29.73%
    Sweet 25.54%
    Alkaline 24.74%
    Amine 23.48%
    Ammoniacal 23.22%
    Cauliflower 22.4%
    Shrimp 21.68%
    Roasted 21.16%
    Cereal 20.0%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    5.4 (weak acid)

    Molecular weight
    84.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    101°C

    Flash point

    • -2.73 ˚C est.

  • Synonyms

    • Epoxycyclopentane
    • Cyclopentane, 1,2-epoxy-
    • Cyclopentene, oxide
    • U3EKO505C5
    • Cyclopentane oxide
    • Cyclopentene epoxide
    • cis-1,2-Epoxycyclopentane
    • HSDB 5421
    • EINECS 206-005-6
    • 1,2-EPOXYCYCLOPENTANE, CIS-
    • 1,2-EPOXYCYCLOPENTANE [HSDB]
    • NSC 148216
    • NSC-148216
    • NSC-196230
    • BRN 0102495
    • AI3-25407
    • 5-17-01-00190 (Beilstein Handbook Reference)
    • cis1,2Epoxycyclopentane
    • Cyclopentane, 1,2epoxy
    • RefChem:411833
    • 6Oxabicyclo(3.1.0)hexane
    • 206-005-6
    • 1,2-EPOXYCYCLOPENTANE
    • 285-67-6
    • CYCLOPENTENE OXIDE
    • (1R,5S)-6-oxabicyclo[3.1.0]hexane
    • 3ZS
    • UNII-U3EKO505C5
    • SCHEMBL3322733
    • (+-)-6-Oxabicyclo(3.1.0)hexane
    • AKOS025117561
    • 6-OXABICYCLO(3.1.0)HEXANE, (+/-)-
    • A819492
    • Q27290640
    • 285-67-6

  • Applications

    1,2-Epoxycyclopentane is primarily used as a reactive intermediate in organic synthesis, enabling ring-opening reactions with nucleophiles to furnish cyclopentyl-containing beta-hydroxy derivatives, amines, and diols. It serves as a building block for epoxy resin and coating formulations, providing a cyclopentyl epoxide moiety that can be opened to form crosslinked networks. It can function as a monomer or co-monomer in polymer synthesis to introduce cyclic aliphatic segments into polyethers or polyols. In pharmaceutical development, it is commonly evaluated as a synthetic intermediate to access cyclopentyl-containing compounds. It is also considered in specialty chemical syntheses, including potential agrochemical intermediates, as a versatile cyclopentyl epoxide building block. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 321.04
    methanol 361.94
    isopropanol 206.94
    water 2.85
    ethyl acetate 141.03
    n-propanol 208.01
    acetone 198.3
    n-butanol 176.13
    acetonitrile 212.21
    DMF 200.73
    toluene 58.21
    isobutanol 140.96
    1,4-dioxane 233.06
    methyl acetate 151.08
    THF 311.77
    2-butanone 161.18
    n-pentanol 124.02
    sec-butanol 153.47
    n-hexane 27.86
    ethylene glycol 148.76
    NMP 169.87
    cyclohexane 32.25
    DMSO 216.32
    n-butyl acetate 111.83
    n-octanol 83.57
    chloroform 591.06
    n-propyl acetate 102.03
    acetic acid 434.29
    dichloromethane 403.38
    cyclohexanone 169.05
    propylene glycol 178.18
    isopropyl acetate 92.6
    DMAc 150.07
    2-ethoxyethanol 191.07
    isopentanol 138.96
    n-heptane 27.1
    ethyl formate 103.42
    1,2-dichloroethane 181.21
    n-hexanol 140.67
    2-methoxyethanol 298.63
    isobutyl acetate 75.55
    tetrachloromethane 82.21
    n-pentyl acetate 76.13
    transcutol 614.46
    n-heptanol 75.98
    ethylbenzene 39.26
    MIBK 84.95
    2-propoxyethanol 239.91
    tert-butanol 170.88
    MTBE 115.32
    2-butoxyethanol 154.01
    propionic acid 214.95
    o-xylene 44.16
    formic acid 178.42
    diethyl ether 133.49
    m-xylene 43.19
    p-xylene 53.56
    chlorobenzene 103.95
    dimethyl carbonate 56.01
    n-octane 11.12
    formamide 170.45
    cyclopentanone 228.12
    2-pentanone 127.16
    anisole 91.91
    cyclopentyl methyl ether 127.36
    gamma-butyrolactone 268.99
    1-methoxy-2-propanol 226.22
    pyridine 208.25
    3-pentanone 93.91
    furfural 242.8
    n-dodecane 11.11
    diethylene glycol 235.34
    diisopropyl ether 47.86
    tert-amyl alcohol 134.08
    acetylacetone 131.88
    n-hexadecane 11.98
    acetophenone 88.56
    methyl propionate 108.56
    isopentyl acetate 101.03
    trichloroethylene 391.28
    n-nonanol 73.61
    cyclohexanol 123.79
    benzyl alcohol 94.23
    2-ethylhexanol 78.74
    isooctanol 61.4
    dipropyl ether 96.11
    1,2-dichlorobenzene 98.51
    ethyl lactate 72.36
    propylene carbonate 153.79
    n-methylformamide 155.6
    2-pentanol 114.42
    n-pentane 29.77
    1-propoxy-2-propanol 168.61
    1-methoxy-2-propyl acetate 120.13
    2-(2-methoxypropoxy) propanol 139.27
    mesitylene 31.36
    ε-caprolactone 159.17
    p-cymene 37.94
    epichlorohydrin 261.1
    1,1,1-trichloroethane 186.83
    2-aminoethanol 213.42
    morpholine-4-carbaldehyde 207.86
    sulfolane 221.72
    2,2,4-trimethylpentane 17.02
    2-methyltetrahydrofuran 205.17
    n-hexyl acetate 113.46
    isooctane 15.17
    2-(2-butoxyethoxy)ethanol 205.99
    sec-butyl acetate 71.24
    tert-butyl acetate 92.04
    decalin 18.71
    glycerin 228.07
    diglyme 322.15
    acrylic acid 217.86
    isopropyl myristate 49.75
    n-butyric acid 224.44
    acetyl acetate 104.52
    di(2-ethylhexyl) phthalate 53.85
    ethyl propionate 84.1
    nitromethane 315.84
    1,2-diethoxyethane 152.49
    benzonitrile 108.79
    trioctyl phosphate 38.4
    1-bromopropane 128.1
    gamma-valerolactone 260.33
    n-decanol 55.34
    triethyl phosphate 48.67
    4-methyl-2-pentanol 72.51
    propionitrile 154.29
    vinylene carbonate 140.77
    1,1,2-trichlorotrifluoroethane 266.74
    DMS 88.45
    cumene 34.17
    2-octanol 49.75
    2-hexanone 100.92
    octyl acetate 60.64
    limonene 52.92
    1,2-dimethoxyethane 207.98
    ethyl orthosilicate 48.0
    tributyl phosphate 48.72
    diacetone alcohol 120.45
    N,N-dimethylaniline 63.67
    acrylonitrile 190.09
    aniline 102.65
    1,3-propanediol 217.04
    bromobenzene 100.58
    dibromomethane 280.4
    1,1,2,2-tetrachloroethane 299.24
    2-methyl-cyclohexyl acetate 75.19
    tetrabutyl urea 53.8
    diisobutyl methanol 55.81
    2-phenylethanol 94.35
    styrene 52.14
    dioctyl adipate 70.29
    dimethyl sulfate 76.52
    ethyl butyrate 85.42
    methyl lactate 95.56
    butyl lactate 79.9
    diethyl carbonate 66.68
    propanediol butyl ether 177.41
    triethyl orthoformate 71.1
    p-tert-butyltoluene 35.79
    methyl 4-tert-butylbenzoate 91.7
    morpholine 261.2
    tert-butylamine 124.6
    n-dodecanol 43.49
    dimethoxymethane 135.76
    ethylene carbonate 114.87
    cyrene 105.85
    2-ethoxyethyl acetate 112.87
    2-ethylhexyl acetate 79.12
    1,2,4-trichlorobenzene 119.85
    4-methylpyridine 131.46
    dibutyl ether 83.43
    2,6-dimethyl-4-heptanol 55.81
    DEF 117.4
    dimethyl isosorbide 154.45
    tetrachloroethylene 211.26
    eugenol 94.64
    triacetin 131.88
    span 80 124.99
    1,4-butanediol 104.67
    1,1-dichloroethane 223.25
    2-methyl-1-pentanol 97.66
    methyl formate 108.3
    2-methyl-1-butanol 126.45
    n-decane 16.91
    butyronitrile 141.43
    3,7-dimethyl-1-octanol 85.59
    1-chlorooctane 48.72
    1-chlorotetradecane 24.46
    n-nonane 16.14
    undecane 13.24
    tert-butylcyclohexane 18.71
    cyclooctane 13.82
    cyclopentanol 154.07
    tetrahydropyran 193.26
    tert-amyl methyl ether 85.33
    2,5,8-trioxanonane 211.69
    1-hexene 75.69
    2-isopropoxyethanol 142.36
    2,2,2-trifluoroethanol 148.38
    methyl butyrate 102.63

    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