o-Iodophenol

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  • Identifiers

    CAS number
    533-58-4

    Molecular formula
    C6H5IO

    SMILES
    C1=CC=C(C(=C1)O)I

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 83.64%
    Smoky 58.9%
    Medicinal 57.28%
    Burnt 52.53%
    Spicy 38.96%
    Sweet 37.06%
    Meaty 36.4%
    Vanilla 33.22%
    Savory 26.8%
    Musty 26.67%

     

    Flavor
    Phenolic 66.74%
    Medicinal 41.24%
    Meaty 39.06%
    Mild 35.08%
    Phenol 33.88%
    Sulfurous 33.08%
    Smoke 28.35%
    Bitter 26.69%
    Medical 25.24%
    Egg 25.05%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    7.88 (neutral)

    Molecular weight
    220.01 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    241°C

    Flash point

    • 98.39 ˚C est.

  • Synonyms

    • 2-IODOPHENOL
    • 533-58-4
    • o-Iodophenol
    • Phenol, 2-iodo-
    • Phenol, o-iodo-
    • o-Jodphenol
    • o-Jodfenol
    • 2-Jodfenol
    • o-Jodfenol [Czech]
    • 2-Jodfenol [Czech]
    • 2-iodanylphenol
    • 2-Jodphenol
    • MFCD00013963
    • Iodophenol
    • NSC 9245
    • EINECS 208-569-9
    • BRN 1855300
    • CHEBI:16706
    • F27L34A8B9
    • NSC-9245
    • 30587-23-6
    • O-IODOPHENOL [MI]
    • DTXSID5052175
    • 4-06-00-01070 (Beilstein Handbook Reference)
    • Phenol, iodo-
    • NSC 9245; o-Iodophenol;
    • oJodfenol
    • 2iodophenol
    • UNII-F27L34A8B9
    • ortho-iodophenol
    • 2Jodfenol
    • Phenol, oiodo
    • 2-iodo phenol
    • 2-iodo-phenol
    • Phenol, 2iodo
    • 2-Iodophenol (2IP)
    • 2-Iodophenol, 98%
    • WLN: QR BI
    • SCHEMBL5720
    • CHEMBL225564
    • DTXCID5030745
    • NSC9245
    • BDBM217397
    • STR06375
    • STL280542
    • AKOS009156984
    • AC-4390
    • CS-W008896
    • PS-7876
    • BP-21314
    • SY005097
    • DB-014125
    • I0460
    • NS00032730
    • EN300-39648
    • C01874
    • H11264
    • A829536
    • Q27102035
    • Z384970702
    • 208-569-9
    • 6X8

  • Applications

    o-Iodophenol (CAS 533-58-4) is an aryl iodide commonly used as a versatile intermediate in organic synthesis. In pharmaceutical and agrochemical development, it frequently serves as a building block for Pd-catalyzed cross-coupling reactions (such as Suzuki, Sonogashira, Kumada) to form biaryl and aryl–alkynyl motifs, enabling rapid assembly of complex scaffolds. It also functions as a precursor for phenol derivatives used in dye and pigment chemistry, and for functionalized monomers in polymer and resin formulations. In materials science and electronics, it can be employed to introduce iodine handles for conjugated systems and potential organic electronic components. As a synthetic intermediate, it is often explored for constructing heterocycles and related medicinal chemistry motifs, with applications that depend on formulation and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 133.17
    methanol 104.35
    isopropanol 98.99
    water 1.09
    ethyl acetate 104.57
    n-propanol 114.75
    acetone 147.81
    n-butanol 108.16
    acetonitrile 46.67
    DMF 212.7
    toluene 33.39
    isobutanol 75.15
    1,4-dioxane 290.12
    methyl acetate 105.18
    THF 468.21
    2-butanone 131.0
    n-pentanol 113.11
    sec-butanol 94.79
    n-hexane 9.54
    ethylene glycol 45.82
    NMP 207.17
    cyclohexane 8.41
    DMSO 221.17
    n-butyl acetate 125.16
    n-octanol 67.93
    chloroform 120.89
    n-propyl acetate 118.53
    acetic acid 102.26
    dichloromethane 90.76
    cyclohexanone 147.76
    propylene glycol 45.67
    isopropyl acetate 97.81
    DMAc 182.89
    2-ethoxyethanol 238.61
    isopentanol 91.61
    n-heptane 21.18
    ethyl formate 84.72
    1,2-dichloroethane 71.81
    n-hexanol 109.96
    2-methoxyethanol 265.31
    isobutyl acetate 83.73
    tetrachloromethane 25.65
    n-pentyl acetate 106.36
    transcutol 609.01
    n-heptanol 74.04
    ethylbenzene 27.27
    MIBK 113.71
    2-propoxyethanol 249.73
    tert-butanol 122.9
    MTBE 121.25
    2-butoxyethanol 170.87
    propionic acid 65.66
    o-xylene 30.55
    formic acid 54.17
    diethyl ether 128.32
    m-xylene 36.45
    p-xylene 31.99
    chlorobenzene 41.93
    dimethyl carbonate 60.63
    n-octane 9.57
    formamide 102.74
    cyclopentanone 203.08
    2-pentanone 131.75
    anisole 110.17
    cyclopentyl methyl ether 164.99
    gamma-butyrolactone 200.33
    1-methoxy-2-propanol 222.07
    pyridine 100.06
    3-pentanone 85.56
    furfural 196.62
    n-dodecane 8.26
    diethylene glycol 197.66
    diisopropyl ether 62.49
    tert-amyl alcohol 114.74
    acetylacetone 167.0
    n-hexadecane 9.22
    acetophenone 98.3
    methyl propionate 89.61
    isopentyl acetate 112.03
    trichloroethylene 130.1
    n-nonanol 67.36
    cyclohexanol 82.04
    benzyl alcohol 88.57
    2-ethylhexanol 79.46
    isooctanol 66.53
    dipropyl ether 113.17
    1,2-dichlorobenzene 46.47
    ethyl lactate 73.58
    propylene carbonate 112.53
    n-methylformamide 104.93
    2-pentanol 92.31
    n-pentane 12.51
    1-propoxy-2-propanol 196.71
    1-methoxy-2-propyl acetate 174.71
    2-(2-methoxypropoxy) propanol 183.6
    mesitylene 30.13
    ε-caprolactone 163.76
    p-cymene 40.22
    epichlorohydrin 236.61
    1,1,1-trichloroethane 68.49
    2-aminoethanol 81.83
    morpholine-4-carbaldehyde 322.35
    sulfolane 227.8
    2,2,4-trimethylpentane 10.33
    2-methyltetrahydrofuran 254.64
    n-hexyl acetate 119.56
    isooctane 10.98
    2-(2-butoxyethoxy)ethanol 249.06
    sec-butyl acetate 93.29
    tert-butyl acetate 143.09
    decalin 10.0
    glycerin 80.03
    diglyme 381.17
    acrylic acid 59.18
    isopropyl myristate 71.68
    n-butyric acid 98.31
    acetyl acetate 74.39
    di(2-ethylhexyl) phthalate 62.07
    ethyl propionate 87.7
    nitromethane 171.8
    1,2-diethoxyethane 223.4
    benzonitrile 65.65
    trioctyl phosphate 50.25
    1-bromopropane 49.94
    gamma-valerolactone 333.81
    n-decanol 54.81
    triethyl phosphate 62.91
    4-methyl-2-pentanol 70.6
    propionitrile 55.22
    vinylene carbonate 102.76
    1,1,2-trichlorotrifluoroethane 178.25
    DMS 95.54
    cumene 27.03
    2-octanol 60.52
    2-hexanone 126.55
    octyl acetate 79.43
    limonene 58.28
    1,2-dimethoxyethane 309.71
    ethyl orthosilicate 69.04
    tributyl phosphate 60.95
    diacetone alcohol 190.9
    N,N-dimethylaniline 77.74
    acrylonitrile 59.55
    aniline 63.8
    1,3-propanediol 126.24
    bromobenzene 36.06
    dibromomethane 60.82
    1,1,2,2-tetrachloroethane 108.45
    2-methyl-cyclohexyl acetate 97.63
    tetrabutyl urea 81.17
    diisobutyl methanol 68.96
    2-phenylethanol 106.56
    styrene 31.95
    dioctyl adipate 94.12
    dimethyl sulfate 94.47
    ethyl butyrate 105.23
    methyl lactate 77.22
    butyl lactate 95.88
    diethyl carbonate 66.67
    propanediol butyl ether 137.8
    triethyl orthoformate 92.58
    p-tert-butyltoluene 43.95
    methyl 4-tert-butylbenzoate 120.06
    morpholine 292.81
    tert-butylamine 73.34
    n-dodecanol 44.89
    dimethoxymethane 225.11
    ethylene carbonate 88.53
    cyrene 169.3
    2-ethoxyethyl acetate 166.7
    2-ethylhexyl acetate 93.92
    1,2,4-trichlorobenzene 64.74
    4-methylpyridine 92.78
    dibutyl ether 88.35
    2,6-dimethyl-4-heptanol 68.96
    DEF 143.38
    dimethyl isosorbide 291.16
    tetrachloroethylene 76.2
    eugenol 142.13
    triacetin 137.35
    span 80 154.0
    1,4-butanediol 69.31
    1,1-dichloroethane 64.07
    2-methyl-1-pentanol 93.78
    methyl formate 86.25
    2-methyl-1-butanol 79.22
    n-decane 12.45
    butyronitrile 67.29
    3,7-dimethyl-1-octanol 75.61
    1-chlorooctane 39.71
    1-chlorotetradecane 21.87
    n-nonane 11.29
    undecane 9.84
    tert-butylcyclohexane 12.83
    cyclooctane 6.48
    cyclopentanol 107.19
    tetrahydropyran 198.26
    tert-amyl methyl ether 113.32
    2,5,8-trioxanonane 306.52
    1-hexene 32.84
    2-isopropoxyethanol 189.86
    2,2,2-trifluoroethanol 58.42
    methyl butyrate 106.54

    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