4-Vinylphenol

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  • Identifiers

    CAS number
    2628-17-3

    Molecular formula
    C8H8O

    SMILES
    C=CC1=CC=C(C=C1)O

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1225.33
    • Carbowax: 2361.67

  • Odor profile

    Phenolic 79.06%
    Sweet 71.15%
    Spicy 64.93%
    Medicinal 62.7%
    Bitter 45.43%
    Smoky 44.76%
    Herbal 42.79%
    Musty 40.66%
    Almond 40.07%
    Woody 38.36%

    Scent© AI

  • Properties

    XLogP3-AA
    2.4

    Molecular weight
    120.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    231°C

    Melting point expt.

    • 73.5 °C

    Flash point est.
    99.25 ˚C

    Solubility expt.

    • soluble in water; slightly soluble in fat
    • moderately soluble (in ethanol)

  • Synonyms

    • 4-Vinylphenol
    • 4-Hydroxystyrene
    • 2628-17-3
    • 4-ETHENYLPHENOL
    • p-Vinylphenol
    • Phenol, 4-ethenyl-
    • p-Hydroxystyrene
    • 4-Vinylphenol, 10 wt.% In propylene glycol
    • Phenol, P-vinyl-
    • FEMA No. 3739
    • OA7V1SM8YL
    • 4-Vinyl-Phenol
    • EINECS 220-103-6
    • MFCD00017593
    • BRN 0506844
    • CHEBI:1883
    • VINYLPHENOL, P-
    • P-VINYLPHENOL [FHFI]
    • CHEMBL349881
    • 4-06-00-03775 (Beilstein Handbook Reference)
    • UNII-OA7V1SM8YL
    • paravinyl phenol
    • 4-VP
    • p-Hydroxystyrene; p-Vinylphenol; 4-Ethenylphenol; 4-Hydroxystyrene
    • p-vinyl phenol
    • Para-vinylphenol
    • 4-Ethenyl-phenol
    • 4-Hydroxy styrene
    • Phenol, 4-ethenyl-(9CI)
    • SCHEMBL59328
    • DTXSID7073301
    • SCHEMBL13341430
    • BDBM50017833
    • NSC114470
    • AKOS015891246
    • CS-W005288
    • DS-6347
    • FV71588
    • HY-W005288
    • NSC-114470
    • SY062083
    • 4-Vinylphenol 10 wt.% In propylene glycol
    • DB-008431
    • 4-Vinylphenol, 10 wt % in propylene glycol
    • NS00005416
    • C05627
    • EN300-252561
    • Q4637201
    • 220-103-6

  • Applications

    4-Vinylphenol solution (CAS 2628-17-3) is a versatile pre-monomer employed in the synthesis of specialty polymers such as poly(4-vinylphenol) for organic thin-film-transistor dielectrics, heat-resistant resins, high-adhesion coatings and adhesives; it also serves as a cross-linker or surface-functionalizing agent for silica, carbon and filtration membranes to enhance heavy-metal adsorption, fabricate biosensors, solvent-vapor sensors and antimicrobial barriers; in flavor science the compound is a key precursor to 4-ethylphenol and is therefore used to study wine aroma and spoilage caused by Brettanomyces; additionally, 4-vinylphenol solution acts as a chromatographic reference standard for food, environmental and pharmaceutical analysis and is a building block for the preparation of drug intermediates, polymer antioxidants and high-performance dyes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 906.63
    methanol 317.06
    isopropanol 600.36
    water 0.45
    ethyl acetate 1106.48
    n-propanol 710.19
    acetone 845.34
    n-butanol 575.58
    acetonitrile 795.59
    DMF 509.33
    toluene 113.44
    isobutanol 392.04
    1,4-dioxane 1202.39
    methyl acetate 849.03
    THF 1557.19
    2-butanone 896.69
    n-pentanol 293.66
    sec-butanol 496.71
    n-hexane 22.52
    ethylene glycol 81.75
    NMP 278.31
    cyclohexane 31.38
    DMSO 711.56
    n-butyl acetate 517.68
    n-octanol 163.16
    chloroform 467.69
    n-propyl acetate 360.64
    acetic acid 357.87
    dichloromethane 759.3
    cyclohexanone 490.14
    propylene glycol 141.81
    isopropyl acetate 368.71
    DMAc 376.88
    2-ethoxyethanol 373.05
    isopentanol 367.36
    n-heptane 58.07
    ethyl formate 447.49
    1,2-dichloroethane 478.31
    n-hexanol 423.06
    2-methoxyethanol 654.47
    isobutyl acetate 155.57
    tetrachloromethane 59.87
    n-pentyl acetate 179.68
    transcutol 1286.47
    n-heptanol 159.7
    ethylbenzene 62.53
    MIBK 266.68
    2-propoxyethanol 550.1
    tert-butanol 535.25
    MTBE 497.93
    2-butoxyethanol 242.04
    propionic acid 381.37
    o-xylene 67.06
    formic acid 78.44
    diethyl ether 863.89
    m-xylene 81.36
    p-xylene 69.3
    chlorobenzene 133.53
    dimethyl carbonate 180.59
    n-octane 18.64
    formamide 239.54
    cyclopentanone 747.32
    2-pentanone 681.4
    anisole 221.88
    cyclopentyl methyl ether 430.97
    gamma-butyrolactone 834.32
    1-methoxy-2-propanol 489.22
    pyridine 477.25
    3-pentanone 420.71
    furfural 383.26
    n-dodecane 17.48
    diethylene glycol 251.68
    diisopropyl ether 148.16
    tert-amyl alcohol 389.62
    acetylacetone 470.86
    n-hexadecane 19.36
    acetophenone 160.39
    methyl propionate 625.61
    isopentyl acetate 320.31
    trichloroethylene 626.77
    n-nonanol 138.61
    cyclohexanol 223.93
    benzyl alcohol 127.61
    2-ethylhexanol 211.01
    isooctanol 114.62
    dipropyl ether 402.93
    1,2-dichlorobenzene 105.28
    ethyl lactate 99.94
    propylene carbonate 344.87
    n-methylformamide 384.0
    2-pentanol 344.77
    n-pentane 33.62
    1-propoxy-2-propanol 375.32
    1-methoxy-2-propyl acetate 383.14
    2-(2-methoxypropoxy) propanol 228.2
    mesitylene 50.88
    ε-caprolactone 429.04
    p-cymene 63.4
    epichlorohydrin 1055.17
    1,1,1-trichloroethane 339.74
    2-aminoethanol 216.75
    morpholine-4-carbaldehyde 457.72
    sulfolane 476.73
    2,2,4-trimethylpentane 18.13
    2-methyltetrahydrofuran 1052.03
    n-hexyl acetate 263.4
    isooctane 18.99
    2-(2-butoxyethoxy)ethanol 341.0
    sec-butyl acetate 190.79
    tert-butyl acetate 300.15
    decalin 18.57
    glycerin 137.98
    diglyme 616.31
    acrylic acid 210.17
    isopropyl myristate 111.86
    n-butyric acid 532.56
    acetyl acetate 318.13
    di(2-ethylhexyl) phthalate 80.17
    ethyl propionate 294.96
    nitromethane 769.33
    1,2-diethoxyethane 576.97
    benzonitrile 165.04
    trioctyl phosphate 69.54
    1-bromopropane 320.3
    gamma-valerolactone 692.23
    n-decanol 106.4
    triethyl phosphate 89.29
    4-methyl-2-pentanol 154.78
    propionitrile 560.74
    vinylene carbonate 253.57
    1,1,2-trichlorotrifluoroethane 264.49
    DMS 186.26
    cumene 48.69
    2-octanol 96.61
    2-hexanone 333.37
    octyl acetate 144.32
    limonene 103.91
    1,2-dimethoxyethane 662.53
    ethyl orthosilicate 88.1
    tributyl phosphate 85.19
    diacetone alcohol 313.8
    N,N-dimethylaniline 111.31
    acrylonitrile 482.54
    aniline 148.35
    1,3-propanediol 367.19
    bromobenzene 120.11
    dibromomethane 401.14
    1,1,2,2-tetrachloroethane 357.8
    2-methyl-cyclohexyl acetate 156.44
    tetrabutyl urea 111.57
    diisobutyl methanol 113.46
    2-phenylethanol 164.56
    styrene 77.61
    dioctyl adipate 142.6
    dimethyl sulfate 184.75
    ethyl butyrate 338.87
    methyl lactate 138.79
    butyl lactate 112.78
    diethyl carbonate 178.07
    propanediol butyl ether 179.26
    triethyl orthoformate 165.39
    p-tert-butyltoluene 62.62
    methyl 4-tert-butylbenzoate 153.74
    morpholine 1268.57
    tert-butylamine 291.47
    n-dodecanol 84.23
    dimethoxymethane 627.31
    ethylene carbonate 231.34
    cyrene 152.39
    2-ethoxyethyl acetate 290.82
    2-ethylhexyl acetate 231.66
    1,2,4-trichlorobenzene 124.84
    4-methylpyridine 340.17
    dibutyl ether 243.86
    2,6-dimethyl-4-heptanol 113.46
    DEF 437.71
    dimethyl isosorbide 378.09
    tetrachloroethylene 191.97
    eugenol 141.73
    triacetin 211.48
    span 80 179.51
    1,4-butanediol 107.96
    1,1-dichloroethane 501.22
    2-methyl-1-pentanol 208.87
    methyl formate 296.19
    2-methyl-1-butanol 347.54
    n-decane 27.71
    butyronitrile 550.11
    3,7-dimethyl-1-octanol 145.59
    1-chlorooctane 94.41
    1-chlorotetradecane 42.24
    n-nonane 26.97
    undecane 21.53
    tert-butylcyclohexane 20.75
    cyclooctane 13.2
    cyclopentanol 313.6
    tetrahydropyran 1010.99
    tert-amyl methyl ether 291.39
    2,5,8-trioxanonane 413.52
    1-hexene 124.13
    2-isopropoxyethanol 250.84
    2,2,2-trifluoroethanol 89.81
    methyl butyrate 348.69

    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
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.01%
Agarwood smoke 1 Aquilaria agallocha Roxb., fam. Thymelaeaceae 0.01%
Agarwood smoke 2 Aquilaria agallocha Roxb., fam. Thymelaeaceae 1.22%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.05%
Hedyotis diffusa (Malaysia) Hedyotis diffusa Willd. (syn. Oldenlandia diffusa Roxb.), fam. Rubiaceae 22.2%
Tamarind 3 fruit Tamarindus indica L., fam. Leguminosae 0.3%
Colocasia esculenta (Taro) Colocasia esculenta (L.) Schott, fam. Araceae 3.1%
Premna serratifolia flower bud Premna serratifolia L. (P.obtusifolia Br.R., P.taitensis Sch.),Verbenaceae 0.05%
Mullilam leaf (India) Zanthoxylum rhetsa D.C. syn. Z. limonella (Dennst.) Alston, fam. Rutaceae 0.5%
Coriander fruit 5 8008-52-4 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.08%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 0.23%
Asafoetida headspace 9000-04-8 Ferula assafoetida L., fam. Apiaceae (Umbelliferae) 0.08%