Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

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  • Identifiers

    CAS number
    50-36-2

    Molecular formula
    C17H21NO4

    SMILES
    CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 54.48%
    Green 30.76%
    Sweet 22.78%
    Fruity 22.5%
    Cooling 22.29%
    Grape 22.2%
    Herbal 22.16%
    Balsamic 21.73%
    Floral 21.38%
    Nutty 20.23%

     

    Flavor
    Bitter 85.5%
    Odorless 28.2%
    Bland 24.77%
    Sweet-like 21.93%
    Cedarleaf 20.95%
    Heather 20.22%
    Broom 20.1%
    Orange flower 19.95%
    Genet 19.83%
    Nitrile 19.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    7.87 (neutral)

    Molecular weight
    303.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 98 °C

    Boiling point

    • BP: 187 °C at 0.1 mm Hg

    Flash point

    • 190.63 ˚C est.

    Solubility expt.

    • Crystals; MP 58-63 °C; freely sol in water or alcohol, slightly sol in ether. /Cocaine nitrate dihydrate/
    • White, granular, crystalline powder; sol in water or alcohol. /Cocaine sulfate/
    • In water, 1.8X10+3 mg/L at 22 °C
    • 1 g/600 mL water at 25 °C;1 g/270 mL water at 80 °C
    • Slightly soluble in water
    • 1 g/6.5 mL alcohol; 1 g/0.7 mL chloroform; 1 g/3.5 mL ether; 1 g/12 mL oil turpentine; 1 g/12 mL olive oil; 1 g/30-50 mL liquid petrolatum
    • For more Solubility (Complete) data for Cocaine (7 total), please visit the HSDB record page.

  • Synonyms

    • Allococaine
    • Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
    • 50-36-2
    • Pseudococaine -
    • (+)-Cocaine
    • Cocainzusatze
    • rac-Allococaine
    • 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-
    • (-)-Cocaine base
    • NCGC00159467-02
    • NCGC00159467-03
    • SCHEMBL21931
    • MLS002320697
    • CHEMBL32363
    • DivK1c_000975
    • Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate #
    • SCHEMBL23086019
    • BDBM86207
    • KBio1_000975
    • NINDS_000975
    • ZPUCINDJVBIVPJ-UHFFFAOYSA-N
    • HMS2272A05
    • 21030-42-2
    • 668-19-9
    • AAA66819
    • NFA70414
    • WAA03042
    • STL565195
    • AKOS025401423
    • NSC_446220
    • CAS_50-36-2
    • IDI1_000975
    • 21206-60-0
    • AC-16037
    • SMR001338843
    • NS00133570
    • L000836
    • methyl 8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylate
    • 8-Azabicyclo[3.2.1]octane-2-carboxylicacid,3-(benzoyloxy)-8-methyl-,methyl ester,(1R,2R,3S,5S)-rel-

  • Applications

    Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (CAS 50-36-2) is primarily used as an intermediate and chiral building block in the synthesis of tropane alkaloid derivatives and related compounds; it is commonly evaluated in medicinal chemistry as a scaffold for lead optimization; it serves as a research reagent in asymmetric synthesis and stereochemical studies; and it may function as a precursor for the development of tropane-based pharmaceutical agents.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 25.15
    methanol 46.58
    isopropanol 18.21
    water 1.02
    ethyl acetate 38.13
    n-propanol 26.78
    acetone 69.63
    n-butanol 26.38
    acetonitrile 41.23
    DMF 147.48
    toluene 31.36
    isobutanol 21.86
    1,4-dioxane 98.54
    methyl acetate 42.4
    THF 120.08
    2-butanone 64.25
    n-pentanol 17.65
    sec-butanol 17.55
    n-hexane 0.26
    ethylene glycol 19.65
    NMP 98.92
    cyclohexane 1.42
    DMSO 168.65
    n-butyl acetate 23.17
    n-octanol 4.71
    chloroform 602.85
    n-propyl acetate 22.14
    acetic acid 119.77
    dichloromethane 470.07
    cyclohexanone 115.28
    propylene glycol 20.12
    isopropyl acetate 23.49
    DMAc 181.37
    2-ethoxyethanol 60.54
    isopentanol 27.34
    n-heptane 0.23
    ethyl formate 43.8
    1,2-dichloroethane 212.74
    n-hexanol 13.84
    2-methoxyethanol 108.24
    isobutyl acetate 15.87
    tetrachloromethane 22.76
    n-pentyl acetate 14.06
    transcutol 158.66
    n-heptanol 8.27
    ethylbenzene 10.25
    MIBK 27.28
    2-propoxyethanol 57.51
    tert-butanol 17.13
    MTBE 6.15
    2-butoxyethanol 34.29
    propionic acid 46.46
    o-xylene 17.33
    formic acid 108.7
    diethyl ether 10.81
    m-xylene 19.45
    p-xylene 16.0
    chlorobenzene 65.78
    dimethyl carbonate 34.46
    n-octane 0.15
    formamide 155.65
    cyclopentanone 117.56
    2-pentanone 43.12
    anisole 24.33
    cyclopentyl methyl ether 26.9
    gamma-butyrolactone 132.22
    1-methoxy-2-propanol 65.45
    pyridine 132.28
    3-pentanone 34.89
    furfural 167.76
    n-dodecane 0.24
    diethylene glycol 76.55
    diisopropyl ether 2.68
    tert-amyl alcohol 14.81
    acetylacetone 65.19
    n-hexadecane 0.28
    acetophenone 40.65
    methyl propionate 36.69
    isopentyl acetate 22.51
    trichloroethylene 486.82
    n-nonanol 5.6
    cyclohexanol 33.68
    benzyl alcohol 46.73
    2-ethylhexanol 8.13
    isooctanol 7.66
    dipropyl ether 4.71
    1,2-dichlorobenzene 60.51
    ethyl lactate 24.57
    propylene carbonate 74.51
    n-methylformamide 87.39
    2-pentanol 12.36
    n-pentane 0.33
    1-propoxy-2-propanol 31.17
    1-methoxy-2-propyl acetate 38.24
    2-(2-methoxypropoxy) propanol 40.62
    mesitylene 9.34
    ε-caprolactone 78.38
    p-cymene 6.76
    epichlorohydrin 225.23
    1,1,1-trichloroethane 99.21
    2-aminoethanol 32.23
    morpholine-4-carbaldehyde 111.64
    sulfolane 139.62
    2,2,4-trimethylpentane 0.39
    2-methyltetrahydrofuran 46.37
    n-hexyl acetate 15.23
    isooctane 0.29
    2-(2-butoxyethoxy)ethanol 50.24
    sec-butyl acetate 14.44
    tert-butyl acetate 21.0
    decalin 0.86
    glycerin 56.92
    diglyme 99.34
    acrylic acid 64.27
    isopropyl myristate 6.95
    n-butyric acid 65.11
    acetyl acetate 39.89
    di(2-ethylhexyl) phthalate 16.62
    ethyl propionate 19.71
    nitromethane 178.39
    1,2-diethoxyethane 22.15
    benzonitrile 56.92
    trioctyl phosphate 9.14
    1-bromopropane 41.55
    gamma-valerolactone 174.44
    n-decanol 4.42
    triethyl phosphate 15.37
    4-methyl-2-pentanol 9.59
    propionitrile 34.19
    vinylene carbonate 87.22
    1,1,2-trichlorotrifluoroethane 192.11
    DMS 29.08
    cumene 6.99
    2-octanol 4.03
    2-hexanone 24.17
    octyl acetate 9.86
    limonene 6.84
    1,2-dimethoxyethane 64.86
    ethyl orthosilicate 12.85
    tributyl phosphate 12.35
    diacetone alcohol 38.58
    N,N-dimethylaniline 16.56
    acrylonitrile 64.29
    aniline 56.65
    1,3-propanediol 54.81
    bromobenzene 61.0
    dibromomethane 216.4
    1,1,2,2-tetrachloroethane 331.91
    2-methyl-cyclohexyl acetate 19.91
    tetrabutyl urea 17.69
    diisobutyl methanol 5.35
    2-phenylethanol 36.8
    styrene 13.29
    dioctyl adipate 15.05
    dimethyl sulfate 61.28
    ethyl butyrate 17.59
    methyl lactate 42.77
    butyl lactate 21.57
    diethyl carbonate 17.19
    propanediol butyl ether 29.1
    triethyl orthoformate 14.55
    p-tert-butyltoluene 5.43
    methyl 4-tert-butylbenzoate 30.44
    morpholine 103.38
    tert-butylamine 5.96
    n-dodecanol 3.4
    dimethoxymethane 74.7
    ethylene carbonate 69.1
    cyrene 52.85
    2-ethoxyethyl acetate 32.27
    2-ethylhexyl acetate 16.78
    1,2,4-trichlorobenzene 74.22
    4-methylpyridine 89.52
    dibutyl ether 4.14
    2,6-dimethyl-4-heptanol 5.35
    DEF 46.83
    dimethyl isosorbide 65.19
    tetrachloroethylene 181.18
    eugenol 39.91
    triacetin 30.72
    span 80 27.49
    1,4-butanediol 23.61
    1,1-dichloroethane 136.44
    2-methyl-1-pentanol 19.58
    methyl formate 74.87
    2-methyl-1-butanol 22.89
    n-decane 0.32
    butyronitrile 34.53
    3,7-dimethyl-1-octanol 7.04
    1-chlorooctane 2.39
    1-chlorotetradecane 1.28
    n-nonane 0.22
    undecane 0.27
    tert-butylcyclohexane 0.54
    cyclooctane 0.4
    cyclopentanol 36.32
    tetrahydropyran 50.31
    tert-amyl methyl ether 6.79
    2,5,8-trioxanonane 71.9
    1-hexene 1.89
    2-isopropoxyethanol 34.4
    2,2,2-trifluoroethanol 79.93
    methyl butyrate 29.13

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
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Rinse-off products applied to the hair with some hand contact
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Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
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Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
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Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
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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