methyl 1-methoxy-1H-indole-3-carboxylate

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  • Identifiers

    CAS number
    18377-50-9

    Molecular formula
    C11H11NO3

    SMILES
    COC(=O)C1=CN(C2=CC=CC=C21)OC

    Safety labels

  • Odor profile

    Fragrance
    Floral 60.49%
    Grape 54.11%
    Fruity 48.57%
    Neroli 44.19%
    Sweet 42.37%
    Powdery 36.49%
    Orange 35.04%
    Odorless 30.41%
    Vanilla 29.35%
    Phenolic 26.14%

     

    Flavor
    Bitter 76.8%
    Odorless 28.26%
    Wintergreen 22.45%
    Fruity 21.33%
    Herbal 21.28%
    Orange flower 21.18%
    Aniseed 21.07%
    Parsley 20.8%
    Orange blossom 20.63%
    Ethyl benzoate 20.62%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    4.52 (weak acid)

    Molecular weight
    205.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    342°C

    Melting point expt.

    • 40 - 41 °C

    Flash point

    • 163.81 ˚C est.

  • Synonyms

    • Methyl 1-methoxy-1H-indole-3-carboxylate
    • 18377-50-9
    • Phytoalexine
    • 8A5KL75GTD
    • DTXSID601275200
    • RefChem:1089247
    • DTXCID901705745
    • Methyl 1-methoxyindole-3-carboxylate
    • CHEMBL318151
    • orb3024033
    • SCHEMBL1849453
    • CHEBI:179420
    • Indole-3-carboxylic acid, 1-methoxy-, methyl ester
    • 1H-Indole-3-carboxylic acid, 1-methoxy-, methyl ester
    • 18377-50-9

  • Applications

    methyl 1-methoxy-1H-indole-3-carboxylate is primarily used as a synthetic intermediate, providing a protected indole scaffold for constructing more complex indole derivatives in pharmaceutical and crop-protection development; it is commonly employed as a building block in medicinal chemistry research for library synthesis of indole-based compounds; it may also serve as a precursor in fragrance and flavor applications, contributing to indole-related aroma profiles; additionally, it is sometimes evaluated as a precursor for dye, polymer, or materials applications, where indole esters are developed for specialized purposes. Its use is typically as an intermediate or precursor rather than a final formulation, and actual applications depend on regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 27.58
    methanol 41.2
    isopropanol 19.3
    water 1.13
    ethyl acetate 58.03
    n-propanol 23.21
    acetone 85.04
    n-butanol 21.8
    acetonitrile 53.8
    DMF 166.49
    toluene 32.18
    isobutanol 19.82
    1,4-dioxane 119.97
    methyl acetate 86.39
    THF 139.61
    2-butanone 61.59
    n-pentanol 20.81
    sec-butanol 20.34
    n-hexane 0.82
    ethylene glycol 28.9
    NMP 148.9
    cyclohexane 2.84
    DMSO 96.43
    n-butyl acetate 31.2
    n-octanol 12.78
    chloroform 158.16
    n-propyl acetate 41.58
    acetic acid 65.0
    dichloromethane 215.5
    cyclohexanone 97.57
    propylene glycol 11.99
    isopropyl acetate 31.66
    DMAc 164.06
    2-ethoxyethanol 63.34
    isopentanol 23.96
    n-heptane 1.19
    ethyl formate 59.96
    1,2-dichloroethane 120.64
    n-hexanol 20.51
    2-methoxyethanol 102.47
    isobutyl acetate 29.24
    tetrachloromethane 16.56
    n-pentyl acetate 23.18
    transcutol 70.03
    n-heptanol 13.86
    ethylbenzene 22.27
    MIBK 29.67
    2-propoxyethanol 57.05
    tert-butanol 29.78
    MTBE 21.72
    2-butoxyethanol 35.78
    propionic acid 37.0
    o-xylene 24.09
    formic acid 53.14
    diethyl ether 24.65
    m-xylene 21.39
    p-xylene 31.75
    chlorobenzene 57.47
    dimethyl carbonate 58.72
    n-octane 0.98
    formamide 107.16
    cyclopentanone 128.53
    2-pentanone 43.93
    anisole 54.18
    cyclopentyl methyl ether 44.72
    gamma-butyrolactone 173.17
    1-methoxy-2-propanol 48.05
    pyridine 127.9
    3-pentanone 41.41
    furfural 175.51
    n-dodecane 1.35
    diethylene glycol 71.31
    diisopropyl ether 7.05
    tert-amyl alcohol 25.12
    acetylacetone 76.4
    n-hexadecane 1.57
    acetophenone 61.43
    methyl propionate 59.5
    isopentyl acetate 31.84
    trichloroethylene 233.2
    n-nonanol 13.22
    cyclohexanol 31.13
    benzyl alcohol 54.83
    2-ethylhexanol 15.67
    isooctanol 13.11
    dipropyl ether 14.22
    1,2-dichlorobenzene 58.38
    ethyl lactate 27.29
    propylene carbonate 89.21
    n-methylformamide 86.39
    2-pentanol 13.82
    n-pentane 0.71
    1-propoxy-2-propanol 28.64
    1-methoxy-2-propyl acetate 38.98
    2-(2-methoxypropoxy) propanol 36.58
    mesitylene 11.32
    ε-caprolactone 80.45
    p-cymene 12.95
    epichlorohydrin 184.67
    1,1,1-trichloroethane 70.97
    2-aminoethanol 29.24
    morpholine-4-carbaldehyde 145.49
    sulfolane 140.59
    2,2,4-trimethylpentane 1.15
    2-methyltetrahydrofuran 77.23
    n-hexyl acetate 28.1
    isooctane 0.6
    2-(2-butoxyethoxy)ethanol 40.29
    sec-butyl acetate 28.76
    tert-butyl acetate 32.11
    decalin 3.05
    glycerin 36.84
    diglyme 86.43
    acrylic acid 49.12
    isopropyl myristate 13.96
    n-butyric acid 46.26
    acetyl acetate 47.34
    di(2-ethylhexyl) phthalate 21.19
    ethyl propionate 40.29
    nitromethane 151.96
    1,2-diethoxyethane 30.21
    benzonitrile 60.91
    trioctyl phosphate 13.02
    1-bromopropane 31.04
    gamma-valerolactone 161.01
    n-decanol 11.0
    triethyl phosphate 24.71
    4-methyl-2-pentanol 11.27
    propionitrile 43.81
    vinylene carbonate 105.79
    1,1,2-trichlorotrifluoroethane 113.14
    DMS 45.56
    cumene 15.96
    2-octanol 9.57
    2-hexanone 36.55
    octyl acetate 18.56
    limonene 14.68
    1,2-dimethoxyethane 103.38
    ethyl orthosilicate 22.28
    tributyl phosphate 15.86
    diacetone alcohol 42.0
    N,N-dimethylaniline 38.85
    acrylonitrile 75.6
    aniline 51.61
    1,3-propanediol 43.34
    bromobenzene 55.32
    dibromomethane 95.63
    1,1,2,2-tetrachloroethane 141.45
    2-methyl-cyclohexyl acetate 31.63
    tetrabutyl urea 23.02
    diisobutyl methanol 10.32
    2-phenylethanol 43.21
    styrene 25.94
    dioctyl adipate 23.23
    dimethyl sulfate 83.96
    ethyl butyrate 29.7
    methyl lactate 34.23
    butyl lactate 19.51
    diethyl carbonate 28.9
    propanediol butyl ether 20.74
    triethyl orthoformate 23.95
    p-tert-butyltoluene 11.17
    methyl 4-tert-butylbenzoate 38.23
    morpholine 102.4
    tert-butylamine 15.62
    n-dodecanol 9.09
    dimethoxymethane 102.02
    ethylene carbonate 79.97
    cyrene 58.3
    2-ethoxyethyl acetate 37.26
    2-ethylhexyl acetate 25.81
    1,2,4-trichlorobenzene 69.25
    4-methylpyridine 96.45
    dibutyl ether 13.74
    2,6-dimethyl-4-heptanol 10.32
    DEF 64.6
    dimethyl isosorbide 70.08
    tetrachloroethylene 103.55
    eugenol 44.72
    triacetin 35.96
    span 80 24.12
    1,4-butanediol 22.04
    1,1-dichloroethane 72.55
    2-methyl-1-pentanol 25.28
    methyl formate 104.39
    2-methyl-1-butanol 22.55
    n-decane 1.85
    butyronitrile 37.75
    3,7-dimethyl-1-octanol 13.75
    1-chlorooctane 9.27
    1-chlorotetradecane 4.94
    n-nonane 1.48
    undecane 1.57
    tert-butylcyclohexane 2.31
    cyclooctane 0.97
    cyclopentanol 36.11
    tetrahydropyran 65.52
    tert-amyl methyl ether 20.75
    2,5,8-trioxanonane 65.31
    1-hexene 5.73
    2-isopropoxyethanol 43.49
    2,2,2-trifluoroethanol 54.25
    methyl butyrate 54.89

    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