o-Aminoacetophenone

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  • Identifiers

    CAS number
    551-93-9

    Molecular formula
    C8H9NO

    SMILES
    CC(=O)C1=CC=CC=C1N

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sweet 77.28%
    Floral 65.19%
    Grape 47.92%
    Neroli 42.74%
    Powdery 41.39%
    Hawthorn 41.25%
    Honey 38.1%
    Hay 34.42%
    Phenolic 33.69%
    Fruity 33.43%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    135.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 20 °C

    Boiling point

    • BP 250-252 °C @ 760 MM HG (SOME DECOMP)
    • 85.00 to 90.00 °C. @ 0.50 mm Hg

    Flash point est.
    121.29 ˚C

    Solubility expt.

    • PRACTICALLY INSOL IN WATER; SOL IN ALC
    • SOL IN ETHER
    • Soluble in fats, acetone; Very slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 2'-Aminoacetophenone
    • 551-93-9
    • 1-(2-Aminophenyl)ethanone
    • O-AMINOACETOPHENONE
    • 2-Acetylaniline
    • o-Acetylaniline
    • o-Aminoacetylbenzene
    • 1-Acetyl-2-aminobenzene
    • Acetophenone, 2'-amino-
    • Ethanone, 1-(2-aminophenyl)-
    • 1-(2-Aminophenyl)Ethan-1-One
    • ortho-aminoacetophenone
    • 2'-Amonioacetophenone
    • 1-(2-aminophenyl)-ethanone
    • 2-acetylphenylamine
    • o-Aminophenyl methyl ketone
    • NSC 8820
    • 5 kaal
    • DTXSID4052213
    • HSDB 5494
    • NSC-8820
    • EINECS 209-002-8
    • MFCD00007717
    • 69Y77091BC
    • 1-(2-amino-phenyl)-ethanone
    • AI3-04095
    • 125507-96-2
    • DTXCID6030784
    • FEMA NO. 3906
    • CHEBI:91110
    • O-AMINOACETOPHENONE [HSDB]
    • 2'-AMINOACETOPHENONE [FHFI]
    • Ethanol, 1-(6-imino-2,4-cyclohexadien-1-ylidene)- (9CI)
    • 27941-88-4
    • 2'-Aminoacetophenone, >=98%
    • oAcetylaniline
    • Ethanone, 1-(aminophenyl)-
    • 2Acetylaniline
    • UNII-69Y77091BC
    • 2aminoacetophenone
    • 2-acetyl aniline
    • 6-acetyl-aniline
    • oAminoacetylbenzene
    • 1Acetyl2aminobenzene
    • 2'Amonioacetophenone
    • o-Amino acetophenone
    • orthoaminoacetophenone
    • 2`-Aminoacetophenone
    • aniline, 2-acetyl-
    • 1-acetyl-aminobenzene
    • 2'-Amino acetophenone
    • Acetophenone, 2'amino
    • 1-(Aminophenyl)-Ethanone
    • Ethanone, 1(2aminophenyl)
    • 1-(2'-aminophenyl)ethanone
    • 2'-Aminoacetophenone, 98%
    • SCHEMBL309044
    • 2-(methylcarbonyl)benzeneamine
    • 1-(2-Aminophenyl)ethanone #
    • 1-(2-aminophenyl)-1-ethanone
    • CHEMBL2251601
    • 1-(2-aminophenyl)ethane-1-one
    • 2'-Aminoacetophenone (Standard)
    • Acetophenone, 2'-amino-(8CI)
    • FEMA 3906
    • GTDQGKWDWVUKTI-UHFFFAOYSA-
    • HY-I0501R
    • NSC8820
    • 1-(2-Aminophenyl)ethanone, 9CI
    • CS-D1191
    • HY-I0501
    • STR00923
    • Tox21_304027
    • STL146696
    • AKOS000120944
    • FA37100
    • PS-4579
    • NCGC00357236-01
    • 2'-Aminoacetophenone, analytical standard
    • AC-25881
    • BP-21338
    • CAS-551-93-9
    • SY001368
    • DB-014028
    • DB-275746
    • A0250
    • A7989
    • NS00022361
    • 2 inverted exclamation mark -Aminoacetophenone
    • EN300-18094
    • Q27163057
    • ETHANOL, 1-(6-IMINO-2,4-CYCLOHEXADIEN-1-YLIDENE)-
    • InChI=1/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
    • 209-002-8
    • VNJ

  • Applications

    2′-Aminoacetophenone (o-aminoacetophenone, CAS 551-93-9) serves as a versatile building block in the synthesis of pharmaceuticals such as quinazolinones, indazoles, anti-inflammatory and antibacterial agents, as a heterocycle-forming reagent in organic chemistry, an intermediate for azo dyes, and, because of its characteristic popcorn-like and grape-like odour, it is employed in flavour and aroma studies, quality control of wine and beer, as a biomarker of Pseudomonas aeruginosa infection, and as a chelating analytical reagent for transition-metal determination.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 671.29
    methanol 984.0
    isopropanol 377.39
    water 28.5
    ethyl acetate 438.16
    n-propanol 449.65
    acetone 983.54
    n-butanol 282.24
    acetonitrile 866.07
    DMF 909.69
    toluene 122.15
    isobutanol 234.85
    1,4-dioxane 1454.89
    methyl acetate 548.75
    THF 1637.32
    2-butanone 523.35
    n-pentanol 199.12
    sec-butanol 244.14
    n-hexane 25.59
    ethylene glycol 203.32
    NMP 739.72
    cyclohexane 15.53
    DMSO 1562.54
    n-butyl acetate 115.12
    n-octanol 94.85
    chloroform 472.75
    n-propyl acetate 148.23
    acetic acid 538.01
    dichloromethane 467.85
    cyclohexanone 502.98
    propylene glycol 156.05
    isopropyl acetate 173.27
    DMAc 348.18
    2-ethoxyethanol 363.4
    isopentanol 175.54
    n-heptane 16.06
    ethyl formate 275.41
    1,2-dichloroethane 326.68
    n-hexanol 174.02
    2-methoxyethanol 686.57
    isobutyl acetate 86.63
    tetrachloromethane 87.74
    n-pentyl acetate 86.13
    transcutol 436.41
    n-heptanol 96.18
    ethylbenzene 40.04
    MIBK 173.96
    2-propoxyethanol 342.83
    tert-butanol 330.21
    MTBE 229.24
    2-butoxyethanol 163.8
    propionic acid 373.2
    o-xylene 57.46
    formic acid 346.89
    diethyl ether 449.23
    m-xylene 77.08
    p-xylene 51.32
    chlorobenzene 135.42
    dimethyl carbonate 185.66
    n-octane 8.23
    formamide 508.49
    cyclopentanone 884.98
    2-pentanone 390.8
    anisole 144.97
    cyclopentyl methyl ether 449.84
    gamma-butyrolactone 1004.46
    1-methoxy-2-propanol 414.38
    pyridine 380.89
    3-pentanone 250.14
    furfural 472.81
    n-dodecane 7.49
    diethylene glycol 302.94
    diisopropyl ether 72.67
    tert-amyl alcohol 193.83
    acetylacetone 376.3
    n-hexadecane 8.38
    acetophenone 103.95
    methyl propionate 355.55
    isopentyl acetate 91.84
    trichloroethylene 438.51
    n-nonanol 79.88
    cyclohexanol 191.24
    benzyl alcohol 110.54
    2-ethylhexanol 75.44
    isooctanol 70.29
    dipropyl ether 101.18
    1,2-dichlorobenzene 92.74
    ethyl lactate 82.93
    propylene carbonate 290.74
    n-methylformamide 637.57
    2-pentanol 161.81
    n-pentane 23.24
    1-propoxy-2-propanol 164.53
    1-methoxy-2-propyl acetate 142.5
    2-(2-methoxypropoxy) propanol 105.18
    mesitylene 44.28
    ε-caprolactone 343.06
    p-cymene 27.58
    epichlorohydrin 855.89
    1,1,1-trichloroethane 280.54
    2-aminoethanol 304.46
    morpholine-4-carbaldehyde 609.1
    sulfolane 902.54
    2,2,4-trimethylpentane 11.04
    2-methyltetrahydrofuran 766.0
    n-hexyl acetate 135.02
    isooctane 10.84
    2-(2-butoxyethoxy)ethanol 174.49
    sec-butyl acetate 87.79
    tert-butyl acetate 173.37
    decalin 12.44
    glycerin 244.81
    diglyme 303.85
    acrylic acid 309.06
    isopropyl myristate 51.49
    n-butyric acid 317.79
    acetyl acetate 198.22
    di(2-ethylhexyl) phthalate 46.84
    ethyl propionate 143.9
    nitromethane 1177.14
    1,2-diethoxyethane 136.95
    benzonitrile 139.82
    trioctyl phosphate 42.14
    1-bromopropane 206.16
    gamma-valerolactone 810.01
    n-decanol 58.96
    triethyl phosphate 48.58
    4-methyl-2-pentanol 81.31
    propionitrile 383.38
    vinylene carbonate 246.32
    1,1,2-trichlorotrifluoroethane 296.45
    DMS 119.76
    cumene 31.93
    2-octanol 65.3
    2-hexanone 190.69
    octyl acetate 68.92
    limonene 43.92
    1,2-dimethoxyethane 511.34
    ethyl orthosilicate 47.6
    tributyl phosphate 45.21
    diacetone alcohol 207.95
    N,N-dimethylaniline 82.41
    acrylonitrile 424.34
    aniline 181.33
    1,3-propanediol 362.85
    bromobenzene 110.69
    dibromomethane 307.43
    1,1,2,2-tetrachloroethane 294.23
    2-methyl-cyclohexyl acetate 68.11
    tetrabutyl urea 59.83
    diisobutyl methanol 44.42
    2-phenylethanol 104.25
    styrene 51.76
    dioctyl adipate 61.49
    dimethyl sulfate 286.35
    ethyl butyrate 84.84
    methyl lactate 161.75
    butyl lactate 69.28
    diethyl carbonate 58.87
    propanediol butyl ether 131.94
    triethyl orthoformate 60.44
    p-tert-butyltoluene 28.82
    methyl 4-tert-butylbenzoate 102.34
    morpholine 1146.44
    tert-butylamine 155.58
    n-dodecanol 43.22
    dimethoxymethane 611.38
    ethylene carbonate 214.62
    cyrene 125.12
    2-ethoxyethyl acetate 127.09
    2-ethylhexyl acetate 69.02
    1,2,4-trichlorobenzene 112.63
    4-methylpyridine 325.37
    dibutyl ether 80.79
    2,6-dimethyl-4-heptanol 44.42
    DEF 307.75
    dimethyl isosorbide 178.05
    tetrachloroethylene 191.74
    eugenol 103.84
    triacetin 106.83
    span 80 98.58
    1,4-butanediol 147.68
    1,1-dichloroethane 360.57
    2-methyl-1-pentanol 127.76
    methyl formate 502.11
    2-methyl-1-butanol 170.99
    n-decane 12.56
    butyronitrile 326.07
    3,7-dimethyl-1-octanol 67.25
    1-chlorooctane 54.0
    1-chlorotetradecane 20.94
    n-nonane 12.14
    undecane 9.52
    tert-butylcyclohexane 15.03
    cyclooctane 6.78
    cyclopentanol 318.85
    tetrahydropyran 751.53
    tert-amyl methyl ether 142.33
    2,5,8-trioxanonane 191.17
    1-hexene 90.69
    2-isopropoxyethanol 204.63
    2,2,2-trifluoroethanol 216.05
    methyl butyrate 180.71

    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