2-Methylacetophenone

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  • Identifiers

    CAS number
    26444-19-9

    Molecular formula
    C9H10O

    SMILES
    CC1=CC=CC=C1C(=O)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1749.0

  • Odor profile

    Sweet 92.04%
    Floral 88.85%
    Hawthorn 68.04%
    Powdery 63.2%
    Coumarinic 61.35%
    Cherry 60.83%
    Hay 60.49%
    Almond 55.24%
    Nutty 51.24%
    Anisic 49.96%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    134.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 214.00 °C. @ 760.00 mm Hg

    Flash point est.
    76.46 ˚C

    Solubility expt.

    • Practically insoluble or insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 2'-METHYLACETOPHENONE
    • 577-16-2
    • 1-(o-Tolyl)ethanone
    • 2-Methylacetophenone
    • 2-Acetyltoluene
    • 1-(2-Methylphenyl)ethanone
    • o-Methylacetophenone
    • o-Acetyltoluene
    • 2'-Methylacetylphenone
    • Ethanone, 1-(2-methylphenyl)-
    • Methyl o-tolyl ketone
    • 1-(2-methylphenyl)ethan-1-one
    • Acetophenone, 2'-methyl-
    • methyl 2-methylphenyl ketone
    • ortho-methylacetophenone
    • 1-(2-Tolyl)ethanone
    • MFCD00008734
    • NSC 84233
    • 1-(Methylphenyl)ethan-1-one
    • Ethanone, 1-(methylphenyl)-
    • 1-o-Tolyl-ethanone
    • o-Methyl acetophenone
    • 26444-19-9
    • 2'-methyl-acetophenone
    • 23O5EV975S
    • EINECS 209-408-5
    • EINECS 247-691-7
    • NSC-84233
    • 1-(o-tolyl)ethan-1-one
    • FEMA NO. 4316
    • CHEBI:145958
    • 2-METHYLACETOPHENONE [FHFI]
    • 2-METHYLPHENYL METHYL KETONE
    • oAcetyltoluene
    • 2Acetyltoluene
    • UNII-23O5EV975S
    • oMethylacetophenone
    • 1-o-tolylethanone
    • methyl tolyl ketone
    • NSC84233
    • 2'Methylacetylphenone
    • 1-(o-tolyl)-ethanone
    • 2\'-Methylacetophenone
    • Acetophenone, 2'methyl
    • ortho-methylphenylethanone
    • 1-(Methylphenyl)-Ethanone
    • Ethanone, 1(2methylphenyl)
    • 2?-METHYLACETOPHENONE
    • 1-(2-Methylphenyl)-Ethanone
    • 2'-Methylacetophenone, 98%
    • SCHEMBL112406
    • 1-(2-Methyl-phenyl)-ethanone
    • Acetophenone, 2'methyl (8CI)
    • 2'-Methylacetophenone, >=98%
    • Acetophenone, 2'-methyl-(8CI)
    • DTXSID501015360
    • Acetophenone, 2'-methyl- (8CI)
    • STR03226
    • Ethanone, 1(2methylphenyl) (9CI)
    • AC7820
    • STL146529
    • AKOS000120656
    • CS-W013374
    • Ethanone, 1-(2-methylphenyl)-(9CI)
    • FM64050
    • HY-W012658
    • Ethanone, 1-(2-methylphenyl)- (9CI)
    • AC-15885
    • SY002283
    • DB-014153
    • A8219
    • M0172
    • NS00042916
    • EN300-20993
    • 2 inverted exclamation mark -Methylacetophenone
    • 2'-Methylacetophenone, Vetec(TM) reagent grade, 98%
    • Q27253770
    • F0001-1503
    • 209-408-5

  • Applications

    2-Methylacetophenone (CAS 26444-19-9) is a versatile organic building block widely employed as a synthesis intermediate: it undergoes aldol/Claisen–Schmidt condensations to give chalcones as precursors to heterocycles, forms oximes/hydrazones and semicarbazones for purification/identification and as ligands, participates in Grignard additions to yield tertiary alcohols, α-halogenation, and ring-forming transformations (e.g., Friedländer and related cyclizations) to access quinolines, benzofurans, and indazoles; owing to the transformable acetophenone core and the ortho-methyl group’s steric/electronic influence, it is used to build o-tolyl scaffolds for research and manufacture of intermediates in pharmaceuticals, agrochemicals, dyes, and other fine chemicals, while also serving in SAR tuning, as a reference/internal standard in GC/HPLC–MS, as a precursor to ligands/metal complexes for catalysis, and as a model substrate in method development (e.g., photochemistry and C–H activation).

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1838.19
    methanol 2384.82
    isopropanol 1262.89
    water 19.54
    ethyl acetate 1709.56
    n-propanol 1542.46
    acetone 2103.43
    n-butanol 1208.75
    acetonitrile 3296.86
    DMF 2197.34
    toluene 1076.26
    isobutanol 1056.97
    1,4-dioxane 5474.19
    methyl acetate 1778.92
    THF 4159.44
    2-butanone 1659.88
    n-pentanol 841.23
    sec-butanol 1027.69
    n-hexane 524.52
    ethylene glycol 439.86
    NMP 2431.98
    cyclohexane 612.84
    DMSO 2317.18
    n-butyl acetate 757.61
    n-octanol 472.66
    chloroform 3733.4
    n-propyl acetate 806.39
    acetic acid 1173.74
    dichloromethane 3720.83
    cyclohexanone 2499.84
    propylene glycol 339.51
    isopropyl acetate 799.54
    DMAc 951.83
    2-ethoxyethanol 1167.27
    isopentanol 810.66
    n-heptane 199.13
    ethyl formate 964.03
    1,2-dichloroethane 2631.14
    n-hexanol 908.18
    2-methoxyethanol 1826.95
    isobutyl acetate 456.92
    tetrachloromethane 812.19
    n-pentyl acetate 507.89
    transcutol 2010.51
    n-heptanol 406.46
    ethylbenzene 511.02
    MIBK 722.89
    2-propoxyethanol 1412.79
    tert-butanol 1155.49
    MTBE 1190.3
    2-butoxyethanol 640.23
    propionic acid 1105.68
    o-xylene 482.63
    formic acid 537.82
    diethyl ether 2428.06
    m-xylene 609.11
    p-xylene 529.46
    chlorobenzene 1104.88
    dimethyl carbonate 568.95
    n-octane 104.85
    formamide 941.63
    cyclopentanone 2775.11
    2-pentanone 1456.56
    anisole 951.51
    cyclopentyl methyl ether 2253.62
    gamma-butyrolactone 3069.83
    1-methoxy-2-propanol 1212.82
    pyridine 2125.55
    3-pentanone 1175.11
    furfural 1620.96
    n-dodecane 73.43
    diethylene glycol 938.04
    diisopropyl ether 544.62
    tert-amyl alcohol 825.15
    acetylacetone 1137.83
    n-hexadecane 84.84
    acetophenone 598.55
    methyl propionate 1329.37
    isopentyl acetate 554.74
    trichloroethylene 3175.6
    n-nonanol 391.52
    cyclohexanol 1213.23
    benzyl alcohol 588.36
    2-ethylhexanol 471.58
    isooctanol 311.67
    dipropyl ether 723.09
    1,2-dichlorobenzene 755.61
    ethyl lactate 294.74
    propylene carbonate 1024.72
    n-methylformamide 1645.12
    2-pentanol 819.14
    n-pentane 363.37
    1-propoxy-2-propanol 712.0
    1-methoxy-2-propyl acetate 604.61
    2-(2-methoxypropoxy) propanol 432.3
    mesitylene 356.64
    ε-caprolactone 1818.45
    p-cymene 196.34
    epichlorohydrin 3339.05
    1,1,1-trichloroethane 1999.88
    2-aminoethanol 727.36
    morpholine-4-carbaldehyde 2236.59
    sulfolane 2639.24
    2,2,4-trimethylpentane 116.53
    2-methyltetrahydrofuran 3245.99
    n-hexyl acetate 810.56
    isooctane 102.48
    2-(2-butoxyethoxy)ethanol 715.78
    sec-butyl acetate 503.83
    tert-butyl acetate 729.32
    decalin 214.86
    glycerin 476.86
    diglyme 1336.7
    acrylic acid 873.75
    isopropyl myristate 286.67
    n-butyric acid 1140.45
    acetyl acetate 713.58
    di(2-ethylhexyl) phthalate 194.87
    ethyl propionate 777.77
    nitromethane 2503.27
    1,2-diethoxyethane 927.19
    benzonitrile 859.07
    trioctyl phosphate 176.09
    1-bromopropane 1766.97
    gamma-valerolactone 2905.01
    n-decanol 286.44
    triethyl phosphate 224.62
    4-methyl-2-pentanol 378.6
    propionitrile 1826.25
    vinylene carbonate 986.38
    1,1,2-trichlorotrifluoroethane 1009.1
    DMS 590.56
    cumene 289.04
    2-octanol 327.37
    2-hexanone 939.18
    octyl acetate 376.58
    limonene 325.44
    1,2-dimethoxyethane 1900.9
    ethyl orthosilicate 222.73
    tributyl phosphate 204.06
    diacetone alcohol 696.09
    N,N-dimethylaniline 494.33
    acrylonitrile 1874.28
    aniline 987.28
    1,3-propanediol 945.72
    bromobenzene 1129.14
    dibromomethane 2545.33
    1,1,2,2-tetrachloroethane 2273.69
    2-methyl-cyclohexyl acetate 344.64
    tetrabutyl urea 262.17
    diisobutyl methanol 229.46
    2-phenylethanol 527.0
    styrene 640.04
    dioctyl adipate 319.9
    dimethyl sulfate 785.2
    ethyl butyrate 519.97
    methyl lactate 442.13
    butyl lactate 280.0
    diethyl carbonate 324.28
    propanediol butyl ether 470.78
    triethyl orthoformate 315.16
    p-tert-butyltoluene 197.19
    methyl 4-tert-butylbenzoate 433.89
    morpholine 4524.69
    tert-butylamine 804.31
    n-dodecanol 220.54
    dimethoxymethane 1864.82
    ethylene carbonate 925.35
    cyrene 412.93
    2-ethoxyethyl acetate 611.89
    2-ethylhexyl acetate 457.56
    1,2,4-trichlorobenzene 821.78
    4-methylpyridine 1966.93
    dibutyl ether 642.24
    2,6-dimethyl-4-heptanol 229.46
    DEF 1493.62
    dimethyl isosorbide 716.24
    tetrachloroethylene 1606.27
    eugenol 428.29
    triacetin 469.11
    span 80 410.98
    1,4-butanediol 407.17
    1,1-dichloroethane 2485.76
    2-methyl-1-pentanol 605.52
    methyl formate 1179.06
    2-methyl-1-butanol 859.31
    n-decane 129.62
    butyronitrile 1589.15
    3,7-dimethyl-1-octanol 356.64
    1-chlorooctane 433.87
    1-chlorotetradecane 163.56
    n-nonane 141.98
    undecane 94.99
    tert-butylcyclohexane 186.14
    cyclooctane 202.21
    cyclopentanol 1332.77
    tetrahydropyran 3920.67
    tert-amyl methyl ether 810.65
    2,5,8-trioxanonane 761.75
    1-hexene 1085.02
    2-isopropoxyethanol 740.87
    2,2,2-trifluoroethanol 443.99
    methyl butyrate 936.91

    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
Orange leaf, sweet (North Africa) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.09%
Orange leaf, sweet (North Africa) 4 Citrus sinensis (L.) Osbeck, cultivar Washington navel, fam. Rutaceae 1.0%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.03%
Micromeria carminea (Turkey) Micromeria carminea P.H. Davis (syn.M.cristata), fam. Lamiaceae (Labiatae) 0.25%
Citron (Vietnam) peel 1a Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.01%
Citron (Vietnam) peel 1b Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.01%