Indole-3-acetonitrile

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  • Identifiers

    CAS number
    771-51-7

    Molecular formula
    C10H8N2

    SMILES
    C1=CC=C2C(=C1)C(=CN2)CC#N

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 55.82%
    Animal 32.01%
    Sweet 28.46%
    Neroli 26.61%
    Fruity 26.2%
    Bitter 25.18%
    Grape 24.53%
    Burnt 23.66%
    Citrus 23.2%
    Honey 22.42%

     

    Flavor
    Bitter 79.31%
    Odorless 27.82%
    Nitrile 21.4%
    Very strong 20.19%
    Indole 19.68%
    Mild 18.93%
    Scallion 18.36%
    Moth ball 18.35%
    Taco 18.22%
    Bread crust 18.22%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    5.57 (weak acid)

    Molecular weight
    156.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    407°C

    Melting point expt.

    • 35 - 37 °C

    Flash point

    • 179.96 ˚C est.

  • Synonyms

    • 3-Indoleacetonitrile
    • 771-51-7
    • Indole-3-acetonitrile
    • 2-(1H-indol-3-yl)acetonitrile
    • 3-Indolylacetonitrile
    • 1H-Indole-3-acetonitrile
    • 3-(Cyanomethyl)indole
    • Indolylacetonitrile
    • Indoleacetonitrile
    • Acetonitrile, 3-indolyl-
    • (indol-3-yl)acetonitrile
    • AG97OFW8JW
    • NSC-523272
    • DTXSID5061118
    • CHEBI:17566
    • RefChem:790963
    • DTXCID1047944
    • 212-232-1
    • 1H-Indol-3-ylacetonitrile
    • Indolylacetonitril
    • 3-Indolacetonitrile
    • Indol-3-ylacetonitrile
    • USAF CB-29
    • (3-Indolyl)acetonitrile
    • 3-Cyanomethyl-1H-indole
    • MFCD00005628
    • Indolyl-3-acetonitrile
    • (1H-indol-3-yl)-acetonitrile
    • (1H-Indol-3-yl)acetonitrile
    • NSC 523272
    • 3-indolyl-Acetonitrile
    • (Indole-3-yl)acetonitrile
    • CHEMBL1812654
    • IAN
    • 2-indol-3-ylethanenitrile
    • CCRIS 5807
    • EINECS 212-232-1
    • BRN 0125488
    • AI3-50105
    • 3-cyanomethylindole
    • b-Indoleacetonitrile
    • indole-3-acetonotrile
    • beta-Indoleacetonitrile
    • indole-3-ylacetonitrile
    • .beta.-Indoleacetonitrile
    • UNII-AG97OFW8JW
    • beta-indole-3-acetonitrile
    • bmse000488
    • 1H-indole-3-ylacetonitrile
    • 3-Indoleacetonitrile, 98%
    • 5-22-03-00074 (Beilstein Handbook Reference)
    • 1H-Indol-3-ylacetonitrile #
    • BIDD:GT0196
    • SCHEMBL149254
    • WLN: T56 BMJ D1CN
    • 2(1H-indol-3-yl)acetonitrile
    • orb1299287
    • orb3026028
    • SCHEMBL8086115
    • SCHEMBL15515402
    • SCHEMBL29521038
    • DMCPFOBLJMLSNX-UHFFFAOYSA-
    • MSK1974
    • 2-(1H-indol-3-yl)-acetonitrile
    • GLXC-26570
    • BB_NC-02787
    • HY-Y0136
    • BDBM50350241
    • NSC523272
    • s6043
    • SBB055967
    • STK802120
    • AKOS000120379
    • CS-W008768
    • EBC-152191
    • FI16427
    • MB00159
    • PS-3276
    • AC-10572
    • I0024
    • NS00014724
    • ST45242079
    • EN300-20368
    • 3-Indoleacetonitrile, purum, >=96.0% (GC)
    • C02938
    • F068786
    • BRD-K65452854-001-01-5
    • Q27102461
    • Z104477894
    • 71C17B3A-CA19-4822-A4E7-D424F7074B4C
    • InChI=1/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
    • 3BO
    • 771-51-7

  • Applications

    Indole-3-acetonitrile (CAS 771-51-7) is a versatile organic synthesis intermediate used as a building block for indole-containing compounds. It is commonly employed to prepare indole derivatives in pharmaceutical and agrochemical research and production. It also serves as a precursor for indole-based dyes and pigments in industrial manufacturing, leveraging its nitrile functionality to enable diverse synthetic routes. Additionally, as a flexible nitrile-bearing building block, it supports complex indole syntheses in general organic chemistry and related formulation work; use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.11
    methanol 25.72
    isopropanol 7.29
    water 1.34
    ethyl acetate 23.89
    n-propanol 13.1
    acetone 41.77
    n-butanol 8.12
    acetonitrile 16.24
    DMF 51.57
    toluene 2.55
    isobutanol 8.68
    1,4-dioxane 32.12
    methyl acetate 36.72
    THF 90.51
    2-butanone 43.92
    n-pentanol 11.74
    sec-butanol 9.55
    n-hexane 0.38
    ethylene glycol 21.93
    NMP 201.84
    cyclohexane 0.22
    DMSO 117.5
    n-butyl acetate 29.3
    n-octanol 7.03
    chloroform 13.09
    n-propyl acetate 29.37
    acetic acid 52.97
    dichloromethane 18.74
    cyclohexanone 42.78
    propylene glycol 16.41
    isopropyl acetate 16.21
    DMAc 124.96
    2-ethoxyethanol 52.83
    isopentanol 9.54
    n-heptane 0.65
    ethyl formate 20.93
    1,2-dichloroethane 18.33
    n-hexanol 14.43
    2-methoxyethanol 56.64
    isobutyl acetate 19.0
    tetrachloromethane 4.8
    n-pentyl acetate 20.68
    transcutol 198.96
    n-heptanol 9.12
    ethylbenzene 3.68
    MIBK 16.48
    2-propoxyethanol 51.3
    tert-butanol 10.39
    MTBE 9.26
    2-butoxyethanol 32.93
    propionic acid 35.26
    o-xylene 3.65
    formic acid 61.35
    diethyl ether 7.3
    m-xylene 2.79
    p-xylene 5.43
    chlorobenzene 10.03
    dimethyl carbonate 28.58
    n-octane 0.26
    formamide 106.62
    cyclopentanone 101.76
    2-pentanone 20.54
    anisole 25.36
    cyclopentyl methyl ether 20.38
    gamma-butyrolactone 153.72
    1-methoxy-2-propanol 33.17
    pyridine 28.78
    3-pentanone 21.52
    furfural 136.53
    n-dodecane 0.28
    diethylene glycol 63.96
    diisopropyl ether 3.64
    tert-amyl alcohol 13.4
    acetylacetone 51.62
    n-hexadecane 0.31
    acetophenone 37.02
    methyl propionate 27.61
    isopentyl acetate 28.94
    trichloroethylene 44.9
    n-nonanol 6.86
    cyclohexanol 7.27
    benzyl alcohol 21.33
    2-ethylhexanol 10.46
    isooctanol 8.27
    dipropyl ether 10.25
    1,2-dichlorobenzene 15.61
    ethyl lactate 26.45
    propylene carbonate 69.26
    n-methylformamide 50.44
    2-pentanol 5.24
    n-pentane 0.19
    1-propoxy-2-propanol 32.1
    1-methoxy-2-propyl acetate 45.46
    2-(2-methoxypropoxy) propanol 50.57
    mesitylene 2.06
    ε-caprolactone 53.56
    p-cymene 5.68
    epichlorohydrin 119.7
    1,1,1-trichloroethane 14.21
    2-aminoethanol 27.67
    morpholine-4-carbaldehyde 128.81
    sulfolane 198.71
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 48.34
    n-hexyl acetate 26.07
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 59.56
    sec-butyl acetate 19.79
    tert-butyl acetate 21.53
    decalin 0.7
    glycerin 39.88
    diglyme 116.41
    acrylic acid 48.11
    isopropyl myristate 10.15
    n-butyric acid 24.79
    acetyl acetate 24.61
    di(2-ethylhexyl) phthalate 17.93
    ethyl propionate 25.31
    nitromethane 134.25
    1,2-diethoxyethane 31.13
    benzonitrile 20.89
    trioctyl phosphate 11.51
    1-bromopropane 4.46
    gamma-valerolactone 128.88
    n-decanol 5.17
    triethyl phosphate 19.99
    4-methyl-2-pentanol 5.1
    propionitrile 11.86
    vinylene carbonate 50.57
    1,1,2-trichlorotrifluoroethane 106.0
    DMS 45.28
    cumene 4.49
    2-octanol 5.55
    2-hexanone 30.01
    octyl acetate 14.08
    limonene 7.09
    1,2-dimethoxyethane 64.74
    ethyl orthosilicate 16.3
    tributyl phosphate 15.12
    diacetone alcohol 32.29
    N,N-dimethylaniline 17.48
    acrylonitrile 20.49
    aniline 10.3
    1,3-propanediol 24.06
    bromobenzene 7.7
    dibromomethane 7.59
    1,1,2,2-tetrachloroethane 32.78
    2-methyl-cyclohexyl acetate 26.27
    tetrabutyl urea 20.36
    diisobutyl methanol 5.57
    2-phenylethanol 22.87
    styrene 3.96
    dioctyl adipate 21.7
    dimethyl sulfate 81.18
    ethyl butyrate 25.86
    methyl lactate 32.82
    butyl lactate 27.36
    diethyl carbonate 22.95
    propanediol butyl ether 35.65
    triethyl orthoformate 19.25
    p-tert-butyltoluene 5.01
    methyl 4-tert-butylbenzoate 35.09
    morpholine 40.22
    tert-butylamine 4.45
    n-dodecanol 3.84
    dimethoxymethane 33.81
    ethylene carbonate 35.09
    cyrene 62.88
    2-ethoxyethyl acetate 44.1
    2-ethylhexyl acetate 23.21
    1,2,4-trichlorobenzene 24.63
    4-methylpyridine 18.51
    dibutyl ether 7.46
    2,6-dimethyl-4-heptanol 5.57
    DEF 27.89
    dimethyl isosorbide 89.22
    tetrachloroethylene 25.7
    eugenol 40.76
    triacetin 52.77
    span 80 30.54
    1,4-butanediol 18.2
    1,1-dichloroethane 8.77
    2-methyl-1-pentanol 13.63
    methyl formate 42.99
    2-methyl-1-butanol 10.36
    n-decane 0.4
    butyronitrile 8.07
    3,7-dimethyl-1-octanol 8.46
    1-chlorooctane 3.06
    1-chlorotetradecane 1.33
    n-nonane 0.32
    undecane 0.32
    tert-butylcyclohexane 0.74
    cyclooctane 0.12
    cyclopentanol 16.36
    tetrahydropyran 15.58
    tert-amyl methyl ether 10.38
    2,5,8-trioxanonane 79.99
    1-hexene 1.89
    2-isopropoxyethanol 37.89
    2,2,2-trifluoroethanol 47.42
    methyl butyrate 31.29

    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