Benzyl 5-oxopyrrolidine-2-carboxylate

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  • Identifiers

    CAS number
    60555-57-9

    Molecular formula
    C12H13NO3

    SMILES
    C1CC(=O)NC1C(=O)OCC2=CC=CC=C2

    Safety labels

  • Odor profile

    Fragrance
    Sweet 50.69%
    Caramellic 34.69%
    Fruity 31.86%
    Nutty 31.48%
    Odorless 30.31%
    Spicy 29.56%
    Buttery 23.05%
    Bitter 23.03%
    Burnt 22.86%
    Balsamic 22.22%

     

    Flavor
    Bitter 55.01%
    Fruity 30.72%
    Odorless 25.02%
    Sweet 23.15%
    Balsam 22.86%
    Grape 22.27%
    Strawberry 21.54%
    Orange flower 21.17%
    Faint 20.88%
    Orange blossom 20.54%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    6.43 (neutral)

    Molecular weight
    219.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    447°C

    Flash point

    • 194.61 ˚C est.

  • Synonyms

    • benzyl 5-oxopyrrolidine-2-carboxylate
    • 60555-57-9
    • MFCD03654596
    • Benzyl (S)-5-oxopyrrolidine-2-carboxylate
    • Enamine_003588
    • Oprea1_130188
    • MLS000564812
    • SCHEMBL841868
    • CHEMBL1313337
    • DTXSID00975966
    • HMS1404D02
    • HMS2442F21
    • LKA95161
    • benzyl5-oxopyrrolidine-2-carboxylate
    • AB8226
    • benzyl 5-oxo-2-pyrrolidinecarboxylate
    • IDI1_007231
    • NCGC00246146-01
    • SMR000152026
    • NS00054647
    • EN300-221965
    • 5-Oxo-pyrrolidine-2-carboxylic acid benzyl ester
    • SR-01000035720
    • SR-01000035720-1
    • Benzyl 5-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylate
    • 60555-57-9

  • Applications

    Benzyl 5-oxopyrrolidine-2-carboxylate (CAS 60555-57-9) is a synthetic intermediate and building block used in pharmaceutical synthesis, enabling construction of lactam-containing and nitrogen-rich heterocyclic scaffolds for drug candidates. It is commonly employed in peptide chemistry as a gamma-lactam amino acid derivative with protecting functionality, helping to control sequence and protect reactive groups. Additionally, its versatility allows conversion to more complex intermediates, making it a core building block for lactam libraries and other heterocyclic systems in medicinal chemistry research. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 84.3
    methanol 268.03
    isopropanol 37.13
    water 3.02
    ethyl acetate 82.29
    n-propanol 43.46
    acetone 77.64
    n-butanol 43.0
    acetonitrile 119.87
    DMF 174.58
    toluene 8.41
    isobutanol 27.24
    1,4-dioxane 99.23
    methyl acetate 89.82
    THF 102.26
    2-butanone 77.95
    n-pentanol 44.15
    sec-butanol 34.28
    n-hexane 0.27
    ethylene glycol 39.4
    NMP 45.47
    cyclohexane 0.31
    DMSO 182.79
    n-butyl acetate 38.06
    n-octanol 10.78
    chloroform 98.57
    n-propyl acetate 53.69
    acetic acid 183.37
    dichloromethane 130.54
    cyclohexanone 57.47
    propylene glycol 32.15
    isopropyl acetate 44.07
    DMAc 322.14
    2-ethoxyethanol 186.09
    isopentanol 49.7
    n-heptane 0.34
    ethyl formate 68.83
    1,2-dichloroethane 70.53
    n-hexanol 22.54
    2-methoxyethanol 250.51
    isobutyl acetate 32.95
    tetrachloromethane 2.82
    n-pentyl acetate 17.85
    transcutol 513.79
    n-heptanol 12.84
    ethylbenzene 9.05
    MIBK 43.89
    2-propoxyethanol 94.66
    tert-butanol 47.96
    MTBE 27.12
    2-butoxyethanol 53.9
    propionic acid 56.97
    o-xylene 8.52
    formic acid 198.24
    diethyl ether 27.02
    m-xylene 7.67
    p-xylene 12.97
    chlorobenzene 19.37
    dimethyl carbonate 47.68
    n-octane 0.29
    formamide 397.51
    cyclopentanone 61.94
    2-pentanone 50.85
    anisole 48.58
    cyclopentyl methyl ether 22.31
    gamma-butyrolactone 97.91
    1-methoxy-2-propanol 125.16
    pyridine 83.74
    3-pentanone 34.76
    furfural 148.9
    n-dodecane 0.46
    diethylene glycol 124.68
    diisopropyl ether 5.83
    tert-amyl alcohol 42.34
    acetylacetone 93.96
    n-hexadecane 0.52
    acetophenone 61.12
    methyl propionate 64.2
    isopentyl acetate 39.84
    trichloroethylene 164.62
    n-nonanol 12.0
    cyclohexanol 17.9
    benzyl alcohol 56.43
    2-ethylhexanol 13.43
    isooctanol 12.41
    dipropyl ether 10.85
    1,2-dichlorobenzene 24.86
    ethyl lactate 40.98
    propylene carbonate 63.41
    n-methylformamide 132.69
    2-pentanol 23.69
    n-pentane 0.21
    1-propoxy-2-propanol 49.82
    1-methoxy-2-propyl acetate 60.96
    2-(2-methoxypropoxy) propanol 73.23
    mesitylene 5.05
    ε-caprolactone 61.28
    p-cymene 6.1
    epichlorohydrin 158.35
    1,1,1-trichloroethane 22.78
    2-aminoethanol 66.59
    morpholine-4-carbaldehyde 143.47
    sulfolane 84.89
    2,2,4-trimethylpentane 0.57
    2-methyltetrahydrofuran 38.04
    n-hexyl acetate 26.07
    isooctane 0.39
    2-(2-butoxyethoxy)ethanol 100.84
    sec-butyl acetate 37.42
    tert-butyl acetate 41.71
    decalin 0.76
    glycerin 74.6
    diglyme 208.4
    acrylic acid 66.72
    isopropyl myristate 12.49
    n-butyric acid 80.94
    acetyl acetate 56.37
    di(2-ethylhexyl) phthalate 19.01
    ethyl propionate 43.64
    nitromethane 336.47
    1,2-diethoxyethane 70.52
    benzonitrile 51.31
    trioctyl phosphate 10.49
    1-bromopropane 14.7
    gamma-valerolactone 141.84
    n-decanol 9.43
    triethyl phosphate 21.5
    4-methyl-2-pentanol 19.12
    propionitrile 60.18
    vinylene carbonate 69.12
    1,1,2-trichlorotrifluoroethane 123.85
    DMS 43.53
    cumene 7.45
    2-octanol 7.62
    2-hexanone 45.46
    octyl acetate 15.4
    limonene 6.73
    1,2-dimethoxyethane 200.49
    ethyl orthosilicate 19.63
    tributyl phosphate 15.6
    diacetone alcohol 72.79
    N,N-dimethylaniline 30.71
    acrylonitrile 101.58
    aniline 26.75
    1,3-propanediol 105.71
    bromobenzene 17.13
    dibromomethane 46.24
    1,1,2,2-tetrachloroethane 95.21
    2-methyl-cyclohexyl acetate 28.14
    tetrabutyl urea 21.61
    diisobutyl methanol 9.92
    2-phenylethanol 38.68
    styrene 12.87
    dioctyl adipate 23.89
    dimethyl sulfate 72.76
    ethyl butyrate 34.08
    methyl lactate 49.36
    butyl lactate 26.16
    diethyl carbonate 29.72
    propanediol butyl ether 52.22
    triethyl orthoformate 26.29
    p-tert-butyltoluene 5.4
    methyl 4-tert-butylbenzoate 41.2
    morpholine 111.07
    tert-butylamine 14.91
    n-dodecanol 7.42
    dimethoxymethane 136.05
    ethylene carbonate 54.75
    cyrene 63.71
    2-ethoxyethyl acetate 47.57
    2-ethylhexyl acetate 26.91
    1,2,4-trichlorobenzene 31.38
    4-methylpyridine 61.43
    dibutyl ether 13.47
    2,6-dimethyl-4-heptanol 9.92
    DEF 80.09
    dimethyl isosorbide 94.61
    tetrachloroethylene 48.89
    eugenol 52.15
    triacetin 52.9
    span 80 40.74
    1,4-butanediol 51.66
    1,1-dichloroethane 35.11
    2-methyl-1-pentanol 49.94
    methyl formate 98.8
    2-methyl-1-butanol 37.4
    n-decane 0.6
    butyronitrile 54.92
    3,7-dimethyl-1-octanol 15.43
    1-chlorooctane 3.83
    1-chlorotetradecane 2.13
    n-nonane 0.44
    undecane 0.52
    tert-butylcyclohexane 0.73
    cyclooctane 0.19
    cyclopentanol 16.2
    tetrahydropyran 34.21
    tert-amyl methyl ether 25.1
    2,5,8-trioxanonane 139.84
    1-hexene 2.83
    2-isopropoxyethanol 103.63
    2,2,2-trifluoroethanol 71.78
    methyl butyrate 64.08

    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