4-Hydroxy-3-methoxybenzonitrile

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  • Identifiers

    CAS number
    4421-08-3

    Molecular formula
    C8H7NO2

    SMILES
    COC1=C(C=CC(=C1)C#N)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 76.44%
    Vanilla 69.18%
    Spicy 52.76%
    Phenolic 51.35%
    Powdery 45.17%
    Floral 42.42%
    Smoky 42.31%
    Balsamic 39.08%
    Creamy 38.61%
    Woody 29.87%

     

    Flavor
    Bitter 74.44%
    Mild 28.79%
    Phenolic 27.84%
    Odorless 25.14%
    Eugenol 20.84%
    Ham 20.8%
    Vanilla 20.79%
    Curry 20.77%
    Nitrile 20.13%
    Parsley 19.99%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    7.39 (neutral)

    Molecular weight
    149.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    295°C

    Flash point

    • 121.35 ˚C est.

  • Synonyms

    • 4-Hydroxy-3-methoxybenzonitrile
    • 4421-08-3
    • DTXSID20196070
    • EINECS 224-589-0
    • NSC 158285
    • RefChem:523828
    • DTXCID30118561
    • 224-589-0
    • Vanillonitrile
    • 4-hydroxy-3-methoxy-benzonitrile
    • m-Anisonitrile, 4-hydroxy-
    • MFCD00001820
    • 3-methoxy-4-hydroxybenzonitrile
    • 4-hydroxy-3-methoxybenzenecarbonitrile
    • 2-methoxy-4-cyanophenol
    • 4-cyano-2-methoxyphenol
    • 5-cyano-2-hydroxyanisole
    • 2-methoxy-4-cyano-phenol
    • 4-Hydroxy-meta-anisonitrile
    • SCHEMBL459931
    • SCHEMBL517796
    • SCHEMBL29804271
    • 3-Methoxy-4-hydroxy-benzonitrile
    • BB_SC-12404
    • BBL036404
    • NSC158285
    • SBB019877
    • STK346864
    • AKOS000304372
    • 4-Hydroxy-3-methoxybenzonitrile, 98%
    • CCG-302543
    • FH34049
    • NSC-158285
    • AS-15906
    • CS-0046224
    • H0620
    • NS00031402
    • ST45142047
    • EN300-07946
    • F214569
    • Z56963393
    • F0001-1204
    • InChI=1/C8H7NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,1H
    • 4421-08-3

  • Applications

    4-Hydroxy-3-methoxybenzonitrile (CAS 4421-08-3) is commonly evaluated as an organic synthesis building block, providing a scaffold for pharmaceutical intermediates and for polyphenol-derived compounds; in the fragrance and personal care sector, it may be used as a precursor for fragrance components or phenol-related derivatives; in coatings, inks, and adhesives, it is often explored as a starting point to prepare monomers or specialty additives to improve adhesion and formulation stability; in polymers and materials development, it can serve as a functional aryl nitrile building block for polymeric architectures; and in R&D settings, it is considered a building block for new aryl structures with hydroxyl and methoxy functionality.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 100.73
    methanol 147.9
    isopropanol 67.81
    water 8.47
    ethyl acetate 219.78
    n-propanol 73.06
    acetone 631.56
    n-butanol 44.49
    acetonitrile 386.09
    DMF 670.55
    toluene 25.82
    isobutanol 41.4
    1,4-dioxane 405.86
    methyl acetate 358.13
    THF 593.2
    2-butanone 269.83
    n-pentanol 47.19
    sec-butanol 51.49
    n-hexane 3.31
    ethylene glycol 127.98
    NMP 505.85
    cyclohexane 6.86
    DMSO 1399.58
    n-butyl acetate 93.34
    n-octanol 37.2
    chloroform 178.39
    n-propyl acetate 170.78
    acetic acid 325.8
    dichloromethane 324.93
    cyclohexanone 264.01
    propylene glycol 62.9
    isopropyl acetate 119.38
    DMAc 424.3
    2-ethoxyethanol 201.92
    isopentanol 39.89
    n-heptane 6.97
    ethyl formate 168.17
    1,2-dichloroethane 231.62
    n-hexanol 44.9
    2-methoxyethanol 260.94
    isobutyl acetate 79.42
    tetrachloromethane 31.65
    n-pentyl acetate 68.96
    transcutol 345.72
    n-heptanol 33.04
    ethylbenzene 21.83
    MIBK 93.92
    2-propoxyethanol 129.05
    tert-butanol 106.92
    MTBE 98.59
    2-butoxyethanol 89.1
    propionic acid 157.93
    o-xylene 26.29
    formic acid 238.12
    diethyl ether 112.1
    m-xylene 25.95
    p-xylene 34.58
    chlorobenzene 65.25
    dimethyl carbonate 168.1
    n-octane 4.06
    formamide 556.59
    cyclopentanone 545.94
    2-pentanone 168.6
    anisole 103.57
    cyclopentyl methyl ether 141.52
    gamma-butyrolactone 705.45
    1-methoxy-2-propanol 155.04
    pyridine 187.71
    3-pentanone 136.19
    furfural 409.39
    n-dodecane 4.19
    diethylene glycol 165.46
    diisopropyl ether 34.29
    tert-amyl alcohol 70.98
    acetylacetone 333.66
    n-hexadecane 4.78
    acetophenone 117.7
    methyl propionate 191.76
    isopentyl acetate 74.31
    trichloroethylene 389.05
    n-nonanol 34.06
    cyclohexanol 51.8
    benzyl alcohol 67.77
    2-ethylhexanol 31.32
    isooctanol 28.83
    dipropyl ether 55.19
    1,2-dichlorobenzene 73.97
    ethyl lactate 85.44
    propylene carbonate 237.77
    n-methylformamide 399.85
    2-pentanol 35.04
    n-pentane 3.49
    1-propoxy-2-propanol 81.03
    1-methoxy-2-propyl acetate 116.64
    2-(2-methoxypropoxy) propanol 93.89
    mesitylene 20.2
    ε-caprolactone 210.59
    p-cymene 21.59
    epichlorohydrin 523.13
    1,1,1-trichloroethane 147.33
    2-aminoethanol 99.39
    morpholine-4-carbaldehyde 438.54
    sulfolane 738.49
    2,2,4-trimethylpentane 3.43
    2-methyltetrahydrofuran 257.38
    n-hexyl acetate 88.56
    isooctane 3.2
    2-(2-butoxyethoxy)ethanol 120.58
    sec-butyl acetate 90.82
    tert-butyl acetate 134.18
    decalin 5.3
    glycerin 130.24
    diglyme 303.54
    acrylic acid 186.9
    isopropyl myristate 40.89
    n-butyric acid 119.04
    acetyl acetate 197.2
    di(2-ethylhexyl) phthalate 36.5
    ethyl propionate 126.6
    nitromethane 1204.24
    1,2-diethoxyethane 116.73
    benzonitrile 106.56
    trioctyl phosphate 31.31
    1-bromopropane 56.89
    gamma-valerolactone 496.32
    n-decanol 27.16
    triethyl phosphate 54.59
    4-methyl-2-pentanol 25.77
    propionitrile 148.4
    vinylene carbonate 214.59
    1,1,2-trichlorotrifluoroethane 294.15
    DMS 134.26
    cumene 18.79
    2-octanol 25.27
    2-hexanone 132.22
    octyl acetate 50.78
    limonene 30.23
    1,2-dimethoxyethane 316.9
    ethyl orthosilicate 46.59
    tributyl phosphate 36.92
    diacetone alcohol 140.36
    N,N-dimethylaniline 67.32
    acrylonitrile 238.81
    aniline 57.32
    1,3-propanediol 107.45
    bromobenzene 57.91
    dibromomethane 144.47
    1,1,2,2-tetrachloroethane 219.58
    2-methyl-cyclohexyl acetate 67.64
    tetrabutyl urea 50.12
    diisobutyl methanol 24.86
    2-phenylethanol 59.58
    styrene 30.74
    dioctyl adipate 64.05
    dimethyl sulfate 333.48
    ethyl butyrate 88.9
    methyl lactate 111.84
    butyl lactate 52.93
    diethyl carbonate 70.93
    propanediol butyl ether 80.03
    triethyl orthoformate 63.25
    p-tert-butyltoluene 21.58
    methyl 4-tert-butylbenzoate 94.25
    morpholine 324.58
    tert-butylamine 47.11
    n-dodecanol 22.03
    dimethoxymethane 319.39
    ethylene carbonate 180.51
    cyrene 129.28
    2-ethoxyethyl acetate 123.34
    2-ethylhexyl acetate 58.03
    1,2,4-trichlorobenzene 91.78
    4-methylpyridine 128.17
    dibutyl ether 46.62
    2,6-dimethyl-4-heptanol 24.86
    DEF 194.35
    dimethyl isosorbide 177.55
    tetrachloroethylene 151.47
    eugenol 86.11
    triacetin 143.29
    span 80 65.9
    1,4-butanediol 67.77
    1,1-dichloroethane 153.62
    2-methyl-1-pentanol 38.46
    methyl formate 399.62
    2-methyl-1-butanol 33.84
    n-decane 6.35
    butyronitrile 97.23
    3,7-dimethyl-1-octanol 32.76
    1-chlorooctane 25.39
    1-chlorotetradecane 12.06
    n-nonane 5.88
    undecane 5.07
    tert-butylcyclohexane 5.35
    cyclooctane 2.93
    cyclopentanol 97.96
    tetrahydropyran 212.98
    tert-amyl methyl ether 68.22
    2,5,8-trioxanonane 195.94
    1-hexene 14.89
    2-isopropoxyethanol 126.89
    2,2,2-trifluoroethanol 212.01
    methyl butyrate 160.62

    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