4-(1Z)-1-Propen-1-ylphenol

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  • Identifiers

    CAS number
    85960-81-2

    Molecular formula
    C9H10O

    SMILES
    C/C=C\C1=CC=C(C=C1)O

  • Odor profile

    Phenolic 72.44%
    Spicy 68.27%
    Sweet 67.18%
    Herbal 50.84%
    Medicinal 50.39%
    Woody 43.6%
    Smoky 42.01%
    Anisic 35.61%
    Clove 34.94%
    Musty 33.32%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    9.7 (weak base)

    Molecular weight
    134.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point

    • 79.00 to 80.00 °C. @ 2.30 mm Hg

    Flash point est.
    106.01 ˚C

  • Synonyms

    • (Z)-4-(1-Propenyl)phenol
    • 85960-81-2
    • 4-[(Z)-prop-1-enyl]phenol
    • VQ6PDW0YG3
    • 4-Propenylphenol, (Z)-
    • 4-((Z)-Prop-1-enyl)phenol
    • Phenol, 4-(1Z)-1-propenyl-
    • (Z)-4-(1-Propen-1-yl)phenol
    • FEMA No. 4062, Z-
    • UNII-VQ6PDW0YG3
    • Phenol, 4-(1-propenyl)-, (Z)-
    • Phenol, 4-(1Z)-1-propen-1-yl-
    • 4-(1Z)-1-Propen-1-ylphenol
    • DTXSID101006553
    • p-Anol, dimer
    • (Z)-4-PROPENYLPHENOL
    • SCHEMBL1397053
    • 4-(prop-1-enyl)phenol, dimer
    • 4-PROPENYLPHENOL, CIS-
    • Phenol, 4-(1-propenyl), cis
    • DTXCID60911300
    • CHEBI:178622
    • UMFCIIBZHQXRCJ-IHWYPQMZSA-N
    • NSC71549
    • NSC-71549
    • 4-[(1Z)-prop-1-en-1-yl]phenol
    • Q27291963

  • Applications

    4-(1Z)-1-Propen-1-ylphenol (CAS 85960-81-2) is used mainly as a fine-chemical intermediate in the synthesis of pharmaceuticals, agrochemicals, and fragrance/flavor ingredients, leveraging the phenolic OH as a handle for O-alkylation/esterification and the aromatic ring for cross-coupling, while the Z-propenyl double bond enables epoxidation, hydroboration–oxidation, thiol–ene, and hydrosilylation to diversify derivatives; consequently it serves as a versatile building block to access isoeugenol/allylphenol analogs, to prepare hindered phenolic antioxidants, UV absorbers, and polymer stabilizers, and—after halogenation/boronation—as a substrate for Suzuki/Heck/Sonogashira couplings; in materials science it is employed to make curable phenolic monomers/oligomers (via epoxidation or thiol–ene) for UV-cured coatings, inks, and adhesives, to prime/modify surfaces through phenoxide formation, and as an analytical standard or mechanistic probe in studies of E/Z isomerization, radical processes, and electrophilic aromatic substitution.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2302.6
    methanol 2129.03
    isopropanol 1641.23
    water 1.21
    ethyl acetate 1967.62
    n-propanol 1888.72
    acetone 4153.14
    n-butanol 1383.4
    acetonitrile 2140.74
    DMF 3207.38
    toluene 479.84
    isobutanol 1153.1
    1,4-dioxane 2206.43
    methyl acetate 2155.86
    THF 3539.43
    2-butanone 2929.37
    n-pentanol 1010.52
    sec-butanol 1405.04
    n-hexane 228.71
    ethylene glycol 433.5
    NMP 1923.74
    cyclohexane 107.94
    DMSO 5375.65
    n-butyl acetate 1024.67
    n-octanol 360.03
    chloroform 1324.7
    n-propyl acetate 1054.06
    acetic acid 937.39
    dichloromethane 1416.65
    cyclohexanone 1698.21
    propylene glycol 643.86
    isopropyl acetate 770.61
    DMAc 1570.29
    2-ethoxyethanol 1303.82
    isopentanol 1004.96
    n-heptane 66.28
    ethyl formate 821.51
    1,2-dichloroethane 1456.79
    n-hexanol 868.45
    2-methoxyethanol 2007.97
    isobutyl acetate 504.91
    tetrachloromethane 291.22
    n-pentyl acetate 431.1
    transcutol 4234.42
    n-heptanol 297.08
    ethylbenzene 269.29
    MIBK 795.51
    2-propoxyethanol 1320.55
    tert-butanol 1610.35
    MTBE 1816.1
    2-butoxyethanol 585.21
    propionic acid 1262.81
    o-xylene 241.66
    formic acid 363.51
    diethyl ether 2269.12
    m-xylene 300.03
    p-xylene 261.97
    chlorobenzene 556.86
    dimethyl carbonate 633.95
    n-octane 23.37
    formamide 1045.63
    cyclopentanone 2829.43
    2-pentanone 2080.54
    anisole 787.6
    cyclopentyl methyl ether 1576.18
    gamma-butyrolactone 2559.34
    1-methoxy-2-propanol 1548.11
    pyridine 1383.89
    3-pentanone 1438.67
    furfural 1259.58
    n-dodecane 15.61
    diethylene glycol 836.61
    diisopropyl ether 449.26
    tert-amyl alcohol 1398.81
    acetylacetone 1417.61
    n-hexadecane 18.55
    acetophenone 517.09
    methyl propionate 1767.31
    isopentyl acetate 717.43
    trichloroethylene 2050.45
    n-nonanol 271.7
    cyclohexanol 741.87
    benzyl alcohol 476.36
    2-ethylhexanol 405.85
    isooctanol 224.5
    dipropyl ether 643.41
    1,2-dichlorobenzene 405.86
    ethyl lactate 292.48
    propylene carbonate 933.12
    n-methylformamide 2099.67
    2-pentanol 988.6
    n-pentane 151.26
    1-propoxy-2-propanol 865.92
    1-methoxy-2-propyl acetate 767.75
    2-(2-methoxypropoxy) propanol 527.52
    mesitylene 170.9
    ε-caprolactone 1236.69
    p-cymene 118.11
    epichlorohydrin 2826.65
    1,1,1-trichloroethane 1152.3
    2-aminoethanol 927.12
    morpholine-4-carbaldehyde 1463.79
    sulfolane 2754.7
    2,2,4-trimethylpentane 76.34
    2-methyltetrahydrofuran 2761.64
    n-hexyl acetate 714.31
    isooctane 64.97
    2-(2-butoxyethoxy)ethanol 904.58
    sec-butyl acetate 559.48
    tert-butyl acetate 839.31
    decalin 76.71
    glycerin 598.86
    diglyme 1455.81
    acrylic acid 890.96
    isopropyl myristate 189.89
    n-butyric acid 1122.74
    acetyl acetate 553.79
    di(2-ethylhexyl) phthalate 154.52
    ethyl propionate 865.68
    nitromethane 2587.09
    1,2-diethoxyethane 1223.13
    benzonitrile 531.71
    trioctyl phosphate 129.99
    1-bromopropane 930.13
    gamma-valerolactone 2165.19
    n-decanol 188.26
    triethyl phosphate 175.14
    4-methyl-2-pentanol 416.2
    propionitrile 1382.12
    vinylene carbonate 672.12
    1,1,2-trichlorotrifluoroethane 1145.27
    DMS 522.33
    cumene 156.18
    2-octanol 215.15
    2-hexanone 1262.16
    octyl acetate 260.23
    limonene 203.41
    1,2-dimethoxyethane 1763.28
    ethyl orthosilicate 184.04
    tributyl phosphate 179.78
    diacetone alcohol 1009.51
    N,N-dimethylaniline 369.99
    acrylonitrile 1377.7
    aniline 751.53
    1,3-propanediol 1044.55
    bromobenzene 542.99
    dibromomethane 1002.11
    1,1,2,2-tetrachloroethane 1520.37
    2-methyl-cyclohexyl acetate 315.39
    tetrabutyl urea 217.19
    diisobutyl methanol 218.58
    2-phenylethanol 464.37
    styrene 368.84
    dioctyl adipate 257.54
    dimethyl sulfate 856.41
    ethyl butyrate 536.85
    methyl lactate 498.94
    butyl lactate 346.49
    diethyl carbonate 301.09
    propanediol butyl ether 682.34
    triethyl orthoformate 291.34
    p-tert-butyltoluene 126.1
    methyl 4-tert-butylbenzoate 338.36
    morpholine 2825.14
    tert-butylamine 1000.8
    n-dodecanol 132.48
    dimethoxymethane 1987.79
    ethylene carbonate 608.19
    cyrene 404.4
    2-ethoxyethyl acetate 679.93
    2-ethylhexyl acetate 545.34
    1,2,4-trichlorobenzene 522.49
    4-methylpyridine 1307.09
    dibutyl ether 496.25
    2,6-dimethyl-4-heptanol 218.58
    DEF 1557.31
    dimethyl isosorbide 739.68
    tetrachloroethylene 888.9
    eugenol 359.39
    triacetin 466.26
    span 80 399.11
    1,4-butanediol 420.86
    1,1-dichloroethane 1458.92
    2-methyl-1-pentanol 738.86
    methyl formate 1224.19
    2-methyl-1-butanol 1069.54
    n-decane 31.58
    butyronitrile 1158.11
    3,7-dimethyl-1-octanol 359.26
    1-chlorooctane 196.66
    1-chlorotetradecane 58.78
    n-nonane 34.68
    undecane 21.45
    tert-butylcyclohexane 89.8
    cyclooctane 46.07
    cyclopentanol 1007.65
    tetrahydropyran 2278.16
    tert-amyl methyl ether 1106.83
    2,5,8-trioxanonane 789.0
    1-hexene 763.88
    2-isopropoxyethanol 858.28
    2,2,2-trifluoroethanol 278.45
    methyl butyrate 1013.67

    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

Botanical

Name CAS Botanical Proportion
Wistaria sinensis headspace Wistaria sinensis DC., fam. Leguminosae (Papilionaceae) 0.2%