4-Chloroindole-3-acetic acid

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  • Identifiers

    CAS number
    2519-61-1

    Molecular formula
    C10H8ClNO2

    SMILES
    C1=CC2=C(C(=C1)Cl)C(=CN2)CC(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 41.09%
    Animal 34.45%
    Floral 31.34%
    Grape 29.47%
    Honey 28.78%
    Fruity 28.06%
    Powdery 27.73%
    Musk 27.19%
    Fatty 26.07%
    Phenolic 23.12%

     

    Flavor
    Odorless 60.3%
    Bitter 49.35%
    Mild 47.01%
    Sour 28.74%
    Very mild 24.44%
    Nutty 24.27%
    Bland 24.1%
    Faint 21.84%
    Yeast 21.77%
    Bread crust 21.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    6.27 (neutral)

    Molecular weight
    209.63 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    430°C

    Melting point expt.

    • 179 - 180 °C

    Flash point

    • 213.46 ˚C est.

  • Synonyms

    • 4-Chloroindole-3-acetic acid
    • 2519-61-1
    • 2-(4-chloro-1H-indol-3-yl)acetic acid
    • 4-Cl-Iaa
    • 4-chloro-1H-indole-3-acetic acid
    • RF78HU5XXV
    • NSC-295294
    • CHEBI:20339
    • DTXSID10179857
    • RefChem:98580
    • DTXCID70102348
    • 821-329-3
    • 1H-Indole-3-acetic acid, 4-chloro-
    • MFCD00216155
    • 4-Chloro-IAA
    • (4-chloro-1H-indol-3-yl)acetic acid
    • 4-chloroindolyl-3-acetic acid
    • 4-chloroindoleacetic acid
    • 4-Chloroindole-3-aceticacid
    • 2-(4-Chloro-3-indolyl)acetic Acid
    • NSC295294
    • UNII-RF78HU5XXV
    • 4-chloro-3-indoleacetic acid
    • SCHEMBL154385
    • CHEMBL309993
    • orb2802054
    • SCHEMBL29580629
    • Indole-3-acetic acid, 4-chloro-
    • AKOS005207277
    • CS-W006267
    • FC20239
    • FS-3042
    • NSC 295294
    • PD165928
    • SY030420
    • DB-006778
    • 2-(4-chloranyl-1H-indol-3-yl)ethanoic acid
    • EN300-221682
    • 519C611
    • F077858
    • Q4637117
    • Z1269128767
    • 2519-61-1

  • Applications

    4-Chloroindole-3-acetic acid (CAS 2519-61-1) is primarily used as an organic building block and intermediate in the synthesis of indole-based pharmaceuticals and agrochemicals; in plant sciences and agricultural R&D it serves as an auxin-like scaffold for probing auxin signaling and transport; it provides a versatile starting material for the preparation of further modified chlorinated indole derivatives via subsequent functionalization, enabling library generation in medicinal chemistry; and it is commonly evaluated as a lead scaffold in structure–activity relationship (SAR) studies to explore indole-based bioactive compounds within custom synthesis and process development workflows.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.05
    methanol 1.39
    isopropanol 0.69
    water 0.35
    ethyl acetate 1.53
    n-propanol 1.03
    acetone 1.14
    n-butanol 1.32
    acetonitrile 0.3
    DMF 8.34
    toluene 0.09
    isobutanol 1.04
    1,4-dioxane 0.8
    methyl acetate 1.75
    THF 13.13
    2-butanone 3.12
    n-pentanol 2.14
    sec-butanol 1.66
    n-hexane 0.01
    ethylene glycol 8.21
    NMP 73.36
    cyclohexane 0.0
    DMSO 7.74
    n-butyl acetate 5.69
    n-octanol 1.91
    chloroform 0.04
    n-propyl acetate 4.17
    acetic acid 4.61
    dichloromethane 0.09
    cyclohexanone 3.75
    propylene glycol 7.5
    isopropyl acetate 1.88
    DMAc 48.59
    2-ethoxyethanol 33.3
    isopentanol 2.68
    n-heptane 0.05
    ethyl formate 1.95
    1,2-dichloroethane 0.13
    n-hexanol 3.27
    2-methoxyethanol 35.19
    isobutyl acetate 2.66
    tetrachloromethane 0.03
    n-pentyl acetate 4.54
    transcutol 63.32
    n-heptanol 3.04
    ethylbenzene 0.22
    MIBK 3.38
    2-propoxyethanol 35.76
    tert-butanol 2.46
    MTBE 0.79
    2-butoxyethanol 20.39
    propionic acid 3.92
    o-xylene 0.21
    formic acid 11.34
    diethyl ether 0.25
    m-xylene 0.24
    p-xylene 0.33
    chlorobenzene 0.14
    dimethyl carbonate 3.51
    n-octane 0.02
    formamide 15.53
    cyclopentanone 12.28
    2-pentanone 2.55
    anisole 2.28
    cyclopentyl methyl ether 2.39
    gamma-butyrolactone 23.76
    1-methoxy-2-propanol 26.23
    pyridine 0.81
    3-pentanone 1.4
    furfural 19.38
    n-dodecane 0.03
    diethylene glycol 49.82
    diisopropyl ether 0.29
    tert-amyl alcohol 4.04
    acetylacetone 6.44
    n-hexadecane 0.04
    acetophenone 5.85
    methyl propionate 2.76
    isopentyl acetate 6.74
    trichloroethylene 0.32
    n-nonanol 2.19
    cyclohexanol 0.95
    benzyl alcohol 3.75
    2-ethylhexanol 2.94
    isooctanol 3.27
    dipropyl ether 1.61
    1,2-dichlorobenzene 0.36
    ethyl lactate 13.16
    propylene carbonate 11.48
    n-methylformamide 5.15
    2-pentanol 1.09
    n-pentane 0.01
    1-propoxy-2-propanol 23.21
    1-methoxy-2-propyl acetate 15.78
    2-(2-methoxypropoxy) propanol 32.25
    mesitylene 0.19
    ε-caprolactone 9.92
    p-cymene 0.71
    epichlorohydrin 9.05
    1,1,1-trichloroethane 0.09
    2-aminoethanol 10.63
    morpholine-4-carbaldehyde 41.95
    sulfolane 42.73
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 5.63
    n-hexyl acetate 5.3
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 34.34
    sec-butyl acetate 3.26
    tert-butyl acetate 4.61
    decalin 0.04
    glycerin 31.76
    diglyme 46.0
    acrylic acid 5.79
    isopropyl myristate 2.9
    n-butyric acid 3.93
    acetyl acetate 1.42
    di(2-ethylhexyl) phthalate 6.8
    ethyl propionate 4.52
    nitromethane 6.86
    1,2-diethoxyethane 5.32
    benzonitrile 1.52
    trioctyl phosphate 4.47
    1-bromopropane 0.07
    gamma-valerolactone 27.06
    n-decanol 1.8
    triethyl phosphate 6.1
    4-methyl-2-pentanol 1.67
    propionitrile 0.46
    vinylene carbonate 5.72
    1,1,2-trichlorotrifluoroethane 16.62
    DMS 6.84
    cumene 0.4
    2-octanol 1.83
    2-hexanone 4.89
    octyl acetate 4.44
    limonene 0.8
    1,2-dimethoxyethane 21.44
    ethyl orthosilicate 4.96
    tributyl phosphate 4.95
    diacetone alcohol 19.26
    N,N-dimethylaniline 2.64
    acrylonitrile 0.96
    aniline 0.46
    1,3-propanediol 11.04
    bromobenzene 0.09
    dibromomethane 0.05
    1,1,2,2-tetrachloroethane 0.3
    2-methyl-cyclohexyl acetate 7.47
    tetrabutyl urea 9.24
    diisobutyl methanol 1.81
    2-phenylethanol 5.15
    styrene 0.16
    dioctyl adipate 7.08
    dimethyl sulfate 12.71
    ethyl butyrate 6.68
    methyl lactate 16.32
    butyl lactate 13.62
    diethyl carbonate 5.29
    propanediol butyl ether 22.99
    triethyl orthoformate 6.26
    p-tert-butyltoluene 0.63
    methyl 4-tert-butylbenzoate 13.53
    morpholine 2.13
    tert-butylamine 0.56
    n-dodecanol 1.37
    dimethoxymethane 6.08
    ethylene carbonate 3.88
    cyrene 40.86
    2-ethoxyethyl acetate 10.3
    2-ethylhexyl acetate 4.65
    1,2,4-trichlorobenzene 0.66
    4-methylpyridine 1.02
    dibutyl ether 1.15
    2,6-dimethyl-4-heptanol 1.81
    DEF 5.37
    dimethyl isosorbide 45.61
    tetrachloroethylene 0.25
    eugenol 20.89
    triacetin 12.09
    span 80 18.41
    1,4-butanediol 8.47
    1,1-dichloroethane 0.05
    2-methyl-1-pentanol 3.85
    methyl formate 3.98
    2-methyl-1-butanol 2.82
    n-decane 0.04
    butyronitrile 0.56
    3,7-dimethyl-1-octanol 2.75
    1-chlorooctane 0.29
    1-chlorotetradecane 0.18
    n-nonane 0.03
    undecane 0.04
    tert-butylcyclohexane 0.05
    cyclooctane 0.0
    cyclopentanol 2.64
    tetrahydropyran 0.37
    tert-amyl methyl ether 1.74
    2,5,8-trioxanonane 40.55
    1-hexene 0.09
    2-isopropoxyethanol 20.41
    2,2,2-trifluoroethanol 4.89
    methyl butyrate 6.59

    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