2'-Hydroxyacetophenone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    118-93-4

    Molecular formula
    C8H8O2

    SMILES
    CC(=O)C1=CC=CC=C1O

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1149.0
    • Carbowax: 1760.0

  • Odor profile

    Sweet 92.12%
    Phenolic 70.13%
    Herbal 63.72%
    Hawthorn 57.07%
    Cherry 55.13%
    Almond 54.09%
    Coumarinic 53.92%
    Hay 53.85%
    Vanilla 52.56%
    Balsamic 50.66%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    136.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 4 - 6 °C

    Boiling point

    • 213.00 °C. @ 717.00 mm Hg

    Flash point est.
    103.86 ˚C

  • Synonyms

    • 2'-Hydroxyacetophenone
    • 118-93-4
    • 1-(2-Hydroxyphenyl)ethanone
    • 2-Acetylphenol
    • O-HYDROXYACETOPHENONE
    • o-Acetylphenol
    • o-Hydroxyphenyl methyl ketone
    • 104809-67-8
    • 1-(2-Hydroxyphenyl)Ethan-1-One
    • 2-Hydroxyphenyl methyl ketone
    • Acetophenone, 2'-hydroxy-
    • Ethanone, 1-(2-hydroxyphenyl)-
    • Methyl 2-hydroxyphenyl ketone
    • Acetophenone, o-hydroxy-
    • USAF KE-20
    • 2/'-Hydroxyacetophenone
    • FEMA No. 3548
    • 125507-95-1
    • NSC 16933
    • 2-Hydroxyacetylbenzene
    • MFCD00002219
    • 1-(2-hydroxyphenyl)-ethanone
    • CHEMBL3187012
    • DTXSID7040285
    • 2-Acetophenol
    • NSC-16933
    • 3E533Z76W0
    • 2,4-Cyclohexadien-1-one, 6-(1-hydroxyethylidene)- (9CI)
    • WLN: QR BV1
    • Ethanone, 1-(hydroxyphenyl)-
    • 1189865-36-8
    • FEMA 3548
    • Paracetamol Impurity I
    • 2'-hydroxy-acetophenone
    • EINECS 204-288-0
    • BRN 0386123
    • o-acetyl phenol
    • AI3-12134
    • UNII-3E533Z76W0
    • 1-(2-Hydroxyphenyl)ethanone; Paracetamol Imp. I (EP); 2-Hydroxyacetophenone; Paracetamol Impurity I
    • 2,4-Cyclohexadien-1-one, 6-(1-hydroxyethylidene)-
    • orthohydroxyacetophenone
    • 2`-Hydroxyacetophenone
    • 2\'-Hydroxyacetophenone
    • Ethanone,1-(2-hydroxyphenyl)-, labeled with carbon-14 (9CI)
    • 1-(hydroxyphenyl)ethanone
    • 1-(2-Hydroxyphenyl)etanone
    • SCHEMBL40865
    • 2-Acetophenol;2-Acetylphenol
    • 4-08-00-00320 (Beilstein Handbook Reference)
    • ACETOPHENONE,2-HYDROXY
    • 1-(2-hydroxy-phenyl)ethanone
    • 1-(2-hydroxy phenyl)-ethanone
    • 1-(2-hydroxy-phenyl)-ethanone
    • 2'-Hydroxyacetophenone - 95%
    • DTXCID5020285
    • HY-Y1426R
    • NSC9263
    • 2'-Hydroxyacetophenone, >=98%
    • CHEBI:145716
    • 2'-Hydroxyacetophenone (Standard)
    • 1-(2-Hydroxyphenyl)ethanone, 9CI
    • Acetophenone, 2'-hydroxy- (8CI)
    • HY-Y1426
    • NSC-9263
    • NSC16933
    • NSC44452
    • PXB86536
    • STR00372
    • Tox21_301119
    • 2-HYDROXYACETOPHENONE [FHFI]
    • BBL012126
    • BDBM50140214
    • NSC-44452
    • s9375
    • STL163508
    • 2`-Hydroxyacetophenone 2-Acetylphenol
    • AKOS000118832
    • AC-5622
    • CCG-266129
    • CS-W020051
    • FH64535
    • PS-3396
    • NCGC00248294-01
    • NCGC00257527-01
    • BP-13220
    • CAS-118-93-4
    • FH171307
    • 2'-Hydroxyacetophenone, analytical standard
    • DB-269423
    • H0192
    • NS00020731
    • PARACETAMOL IMPURITY I [EP IMPURITY]
    • EN300-18385
    • 2'-Hydroxyacetophenone, ReagentPlus(R), 99%
    • D70588
    • 2'-Hydroxyacetophenone (Acetaminophen Impurity I)
    • doi:10.14272/JECYUBVRTQDVAT-UHFFFAOYSA-N.1
    • Q27257104
    • Z57101014
    • 2'-Hydroxyacetophenone, Vetec(TM) reagent grade, 98%
    • F1908-0162
    • InChI=1/C8H8O2/c1-6(9)7-4-2-3-5-8(7)10/h2-5,10H,1H

  • Applications

    2'-Hydroxyacetophenone (o-hydroxyacetophenone, CAS 118-93-4) is a versatile organic building block widely used as a synthetic intermediate across pharmaceuticals, agrochemicals and fine chemicals; owing to the ortho-phenolic OH adjacent to the carbonyl, it undergoes Claisen–Schmidt condensations to chalcones that can be transformed into flavanones and flavones via the Baker–Venkataraman route, or cyclized to benzofurans and other aromatics, enabling libraries of bioactive scaffolds (e.g., tyrosinase inhibitors, antimicrobial and antioxidant candidates) for drug discovery; it also serves as a precursor to oximes (such as 2'-hydroxyacetophenone oxime and long-chain analogs) used as selective metal chelating agents/solvent-extraction reagents for Cu(II), Ni(II) and Co(II), and as spectroanalytical reagents; additionally, it furnishes Schiff bases and salicylidene-type ligands that chelate a broad range of metals, with the resulting complexes applied as homogeneous catalysts, functional materials and antimicrobial agents, while its o-hydroxyaryl ketone core is a classic ESIPT fluorophore platform for fluorescent sensors (metal-ion and pH probes) and UV-absorbing/photofunctional coatings and polymers; in research it is also employed as a benchmark molecule to study intramolecular H-bonding, excited-state proton transfer and tautomerism, and as a precursor toward aroma/color intermediates and directing motifs in advanced organic synthesis.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 766.63
    methanol 980.59
    isopropanol 570.22
    water 7.63
    ethyl acetate 645.78
    n-propanol 617.28
    acetone 1153.81
    n-butanol 442.82
    acetonitrile 1036.05
    DMF 1485.2
    toluene 141.23
    isobutanol 384.42
    1,4-dioxane 2156.2
    methyl acetate 687.02
    THF 2682.06
    2-butanone 672.96
    n-pentanol 346.37
    sec-butanol 420.23
    n-hexane 81.47
    ethylene glycol 278.78
    NMP 1189.82
    cyclohexane 47.79
    DMSO 2269.08
    n-butyl acetate 223.28
    n-octanol 185.34
    chloroform 575.03
    n-propyl acetate 328.89
    acetic acid 527.23
    dichloromethane 597.58
    cyclohexanone 742.12
    propylene glycol 220.47
    isopropyl acetate 325.08
    DMAc 509.78
    2-ethoxyethanol 634.94
    isopentanol 312.66
    n-heptane 40.29
    ethyl formate 363.09
    1,2-dichloroethane 511.57
    n-hexanol 321.21
    2-methoxyethanol 1022.21
    isobutyl acetate 195.56
    tetrachloromethane 115.23
    n-pentyl acetate 161.42
    transcutol 859.94
    n-heptanol 162.7
    ethylbenzene 89.15
    MIBK 331.24
    2-propoxyethanol 639.47
    tert-butanol 605.89
    MTBE 422.44
    2-butoxyethanol 289.11
    propionic acid 505.09
    o-xylene 88.78
    formic acid 258.15
    diethyl ether 729.71
    m-xylene 122.8
    p-xylene 106.5
    chlorobenzene 174.58
    dimethyl carbonate 300.98
    n-octane 22.81
    formamide 496.66
    cyclopentanone 1326.62
    2-pentanone 619.08
    anisole 288.78
    cyclopentyl methyl ether 780.97
    gamma-butyrolactone 1527.9
    1-methoxy-2-propanol 780.28
    pyridine 419.04
    3-pentanone 385.13
    furfural 622.36
    n-dodecane 22.18
    diethylene glycol 552.43
    diisopropyl ether 172.62
    tert-amyl alcohol 374.61
    acetylacetone 631.26
    n-hexadecane 24.74
    acetophenone 204.54
    methyl propionate 529.61
    isopentyl acetate 180.38
    trichloroethylene 577.93
    n-nonanol 157.89
    cyclohexanol 342.67
    benzyl alcohol 195.64
    2-ethylhexanol 148.29
    isooctanol 127.27
    dipropyl ether 219.51
    1,2-dichlorobenzene 146.0
    ethyl lactate 170.62
    propylene carbonate 472.03
    n-methylformamide 791.49
    2-pentanol 308.85
    n-pentane 57.38
    1-propoxy-2-propanol 337.1
    1-methoxy-2-propyl acetate 272.96
    2-(2-methoxypropoxy) propanol 221.2
    mesitylene 87.26
    ε-caprolactone 602.08
    p-cymene 52.36
    epichlorohydrin 1334.04
    1,1,1-trichloroethane 400.96
    2-aminoethanol 416.72
    morpholine-4-carbaldehyde 1027.1
    sulfolane 1577.73
    2,2,4-trimethylpentane 27.06
    2-methyltetrahydrofuran 1305.22
    n-hexyl acetate 272.89
    isooctane 30.22
    2-(2-butoxyethoxy)ethanol 364.87
    sec-butyl acetate 205.15
    tert-butyl acetate 367.04
    decalin 37.68
    glycerin 346.94
    diglyme 592.33
    acrylic acid 416.8
    isopropyl myristate 117.42
    n-butyric acid 441.15
    acetyl acetate 302.46
    di(2-ethylhexyl) phthalate 82.92
    ethyl propionate 313.84
    nitromethane 1240.43
    1,2-diethoxyethane 288.66
    benzonitrile 221.44
    trioctyl phosphate 87.41
    1-bromopropane 332.42
    gamma-valerolactone 1195.83
    n-decanol 124.18
    triethyl phosphate 92.98
    4-methyl-2-pentanol 168.64
    propionitrile 523.29
    vinylene carbonate 363.51
    1,1,2-trichlorotrifluoroethane 451.59
    DMS 237.99
    cumene 70.82
    2-octanol 127.24
    2-hexanone 387.94
    octyl acetate 149.34
    limonene 82.3
    1,2-dimethoxyethane 926.65
    ethyl orthosilicate 90.01
    tributyl phosphate 92.2
    diacetone alcohol 406.74
    N,N-dimethylaniline 170.13
    acrylonitrile 567.06
    aniline 215.92
    1,3-propanediol 524.44
    bromobenzene 146.62
    dibromomethane 406.43
    1,1,2,2-tetrachloroethane 436.78
    2-methyl-cyclohexyl acetate 134.67
    tetrabutyl urea 121.75
    diisobutyl methanol 97.72
    2-phenylethanol 187.35
    styrene 104.06
    dioctyl adipate 138.72
    dimethyl sulfate 491.96
    ethyl butyrate 177.72
    methyl lactate 293.69
    butyl lactate 128.3
    diethyl carbonate 113.49
    propanediol butyl ether 251.89
    triethyl orthoformate 119.39
    p-tert-butyltoluene 56.78
    methyl 4-tert-butylbenzoate 192.02
    morpholine 1759.46
    tert-butylamine 305.95
    n-dodecanol 98.03
    dimethoxymethane 1011.4
    ethylene carbonate 322.56
    cyrene 238.57
    2-ethoxyethyl acetate 223.06
    2-ethylhexyl acetate 133.78
    1,2,4-trichlorobenzene 173.25
    4-methylpyridine 399.72
    dibutyl ether 186.49
    2,6-dimethyl-4-heptanol 97.72
    DEF 531.34
    dimethyl isosorbide 367.83
    tetrachloroethylene 272.99
    eugenol 198.9
    triacetin 210.38
    span 80 196.14
    1,4-butanediol 240.76
    1,1-dichloroethane 508.65
    2-methyl-1-pentanol 234.64
    methyl formate 607.2
    2-methyl-1-butanol 288.2
    n-decane 34.01
    butyronitrile 459.47
    3,7-dimethyl-1-octanol 144.99
    1-chlorooctane 118.57
    1-chlorotetradecane 53.88
    n-nonane 33.91
    undecane 27.19
    tert-butylcyclohexane 42.64
    cyclooctane 21.06
    cyclopentanol 547.58
    tetrahydropyran 1281.25
    tert-amyl methyl ether 272.38
    2,5,8-trioxanonane 387.44
    1-hexene 211.94
    2-isopropoxyethanol 404.44
    2,2,2-trifluoroethanol 235.2
    methyl butyrate 381.36

    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
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Anthoxanthum odoratum (Italy) 1a fresh leaf Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.1%
Anthoxanthum odoratum (Italy) 1b hay Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.01%
Myrceugenia alpigena (Brazil) Myrceugenia alpigena (DC.) Landrum, fam. Myrtaceae 9.9%