o-Aminoazotoluene

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  • Identifiers

    CAS number
    97-56-3

    Molecular formula
    C14H15N3

    SMILES
    CC1=CC=CC=C1N=NC2=CC(=C(C=C2)N)C

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Floral 35.56%
    Roasted 34.53%
    Meaty 33.44%
    Burnt 32.28%
    Grape 30.49%
    Sweet 30.19%
    Animal 30.06%
    Neroli 28.27%
    Fruity 26.73%
    Musty 24.85%

     

    Flavor
    Bitter 46.44%
    Roasted 30.65%
    Nutty 24.96%
    Very strong 23.8%
    Indole 23.22%
    Mild 23.01%
    Nitrile 22.89%
    Meaty 22.43%
    Scallion 22.37%
    Coffee 22.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    3.3 (weak acid)

    Molecular weight
    225.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 214 to 216 °F (NTP, 1992)
    • 101-102 °C

    Boiling point

    • Sublimes above 302 °F (NTP, 1992)

    Flash point

    • 199.95 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • SOL IN ALCOHOL, ETHER, CHLOROFORM
    • SOL IN OILS & FATS
    • SOL IN ACETONE, CELLOSOLVE & TOLUENE

  • Synonyms

    • o-Aminoazotoluene
    • 97-56-3
    • Fast Garnet GBC Base
    • 2-Aminoazotoluene
    • Solvent Yellow 3
    • C.I. Solvent Yellow 3
    • Toluazotoluidine
    • Fast Yellow AT
    • Somalia Yellow R
    • Fat Yellow B
    • Aminoazotoluene
    • Sudan Yellow RRA
    • Organol Yellow 2T
    • o-Aminoazotoluol
    • ortho-Aminoazotoluene
    • Waxakol Yellow NL
    • 4-Amino-2',3-dimethylazobenzene
    • 2-AMINO-5-AZOTOLUENE
    • OAAT
    • o-Amidoazotoluol
    • o-Aminoazotolueno
    • 4-(o-Tolylazo)-o-toluidine
    • o-Tolueneazo-o-toluidine
    • Tulabase Fast Garnet GB
    • O-AT
    • 4-o-Tolylazo-o-toluidine
    • Tulabase Fast Garnet GBC
    • 5-(o-Tolylazo)-2-aminotoluene
    • Benzenamine, 2-methyl-4-[(2-methylphenyl)azo]-
    • 2',3-Dimethyl-4-aminoazobenzene
    • o-Toluidine, 4-o-tolylazo-
    • 4'-Amino-2,3'-dimethylazobenzene
    • o-Aminoazotoluene [MI]
    • o-Toluol-azo-o-toluidin
    • o-Toluidine, 4-(o-tolylazo)-
    • CCRIS 25
    • o-Aato-amidoazotoluol
    • Zlut rozpoustedlova 3
    • 4'-Amino-2,3'-azotoluene
    • 4'-Amino-2:3'-azotoluene
    • C.I. 11160
    • 2-methyl-4-[(2-methylphenyl)diazenyl]aniline
    • 61550-68-3
    • C.I. 11160B
    • HSDB 2639
    • 2,3'-Dimethyl-4'-aminoazobenzene
    • UNII-QHZ900P7ZA
    • NSC 1797
    • NSC-1797
    • 2-Methyl-4-((o-tolyl)azo)aniline
    • Orthoaminoazotoluene
    • QHZ900P7ZA
    • NSC-26821
    • o-Aminoazotoluene [WHO-DD]
    • Benzenamine, 2-methyl-4-((2-methylphenyl)azo)-
    • BRN 0745567
    • DTXSID1020069
    • AI3-52505
    • 4-Amino-3,2'-dimethylazobenzene
    • 2-Methyl-4-((2-methylphenyl)diazenyl)amine
    • EINECS 202-591-2
    • 2-Methyl-4-[(E)-(2-methylphenyl)diazenyl]aniline
    • DTXCID4069
    • Benzenamine, 2-methyl-4-((2-methylphenyl)azo)-, (E)-
    • MLS000738066
    • 2-Methyl-4-((2-methylphenyl)azo)benzenamine
    • CHEBI:82285
    • NSC1797
    • 4-16-00-00528 (Beilstein Handbook Reference)
    • NSC26821
    • 2-Methyl-4-[(o-tolyl)azo]aniline
    • MFCD00007733
    • (E)-2-methyl-4-(o-tolyldiazenyl)aniline
    • 4-Amino-2',3-dimethylazobenzene 100 microg/mL in Cyclohexane
    • 2-Methyl-4((2-methylphenyl)azo)benzenamine
    • Aminoazotoluene(indicator)
    • 2-methyl-4-[(2-methylphenyl)azo]benzenamine
    • Orthoaminoasotoluol
    • Orthoaminoasotoluene
    • Azoic diazo component 4, base
    • WLN: ZR B1 DNUNR B1
    • CI Solvent Yellow 3
    • NSC 26821
    • o Aminoazotoluene
    • o-Amidoazotoluol [German]
    • Aminoazotoluene (indicator)
    • CAS-97-56-3
    • o-Aminoazotolueno [Spanish]
    • SMR000393738
    • ortho Aminoazotoluene
    • Zlut rozpoustedlova 3 [Czech]
    • 2-Methyl-4[(2-methylphenyl)azo]benzenamine
    • ortho-Tolueneazo-ortho-toluidine
    • o-Toluol-azo-o-toluidin [German]
    • O-AAT
    • CI 11160B
    • o-Toluene-azo-o-toluidine
    • Benzenamine, 2-methyl-4-(2-(2-methylphenyl)diazenyl)-
    • Benzenamine, 2-methyl-4-[2-(2-methylphenyl)diazenyl]-
    • oAmidoazotoluol
    • oAminoazotoluol
    • CI 11160
    • ortho-Toluol-azo-ortho-toluidin [German]
    • oAminoazotoluene
    • oAminoazotolueno
    • ortho-Toluol-azo-ortho-toluidin
    • 2Amino5azotoluene
    • 4-Aminoazotoluene
    • oToluolazootoluidin
    • oTolueneazootoluidine
    • 4(oTolylazo)otoluidine
    • 4'Amino2:3'azotoluene
    • orthoToluolazoorthotoluidin
    • 5(oTolylazo)2aminotoluene
    • oToluidine, 4(otolylazo)
    • orthoTolueneazoorthotoluidine
    • 2',3Dimethyl4aminoazobenzene
    • 4Amino2',3dimethylazobenzene
    • MLS002152915
    • 2Methyl4((otolyl)azo)aniline
    • CHEMBL83552
    • SCHEMBL411206
    • 2-methyl-4-[2-(2-methylphenyl)diazen-1-yl]aniline
    • Fast Garnet GBC base, 97%
    • CHEMBL1701225
    • SCHEMBL13338328
    • PFRYFZZSECNQOL-UHFFFAOYSA-N
    • C.I. Solvent Yellow 3 (8CI)

  • Applications

    o-Aminoazotoluene (CAS 97-56-3) is primarily used as an intermediate in the synthesis of azo dyes and pigments; it acts as a diazo component for forming a range of azo colorants. It is commonly employed in the textile, paper, and leather dyeing sectors, as well as in printing inks and coatings, and it also serves as a building block in the production of polymer colorants for plastics and other materials. In research and development, it is used to create tailored dye systems and to probe color properties in dye chemistry. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 35.59
    methanol 49.03
    isopropanol 15.73
    water 0.03
    ethyl acetate 349.18
    n-propanol 30.79
    acetone 58.72
    n-butanol 29.81
    acetonitrile 108.05
    DMF 81.93
    toluene 86.95
    isobutanol 12.68
    1,4-dioxane 346.06
    methyl acetate 201.25
    THF 307.2
    2-butanone 141.73
    n-pentanol 23.82
    sec-butanol 20.47
    n-hexane 1.99
    ethylene glycol 3.68
    NMP 25.83
    cyclohexane 2.76
    DMSO 92.46
    n-butyl acetate 113.81
    n-octanol 6.79
    chloroform 373.15
    n-propyl acetate 89.53
    acetic acid 51.74
    dichloromethane 369.37
    cyclohexanone 80.25
    propylene glycol 8.34
    isopropyl acetate 109.27
    DMAc 175.45
    2-ethoxyethanol 106.85
    isopentanol 24.7
    n-heptane 2.43
    ethyl formate 87.4
    1,2-dichloroethane 253.8
    n-hexanol 27.33
    2-methoxyethanol 148.92
    isobutyl acetate 46.86
    tetrachloromethane 14.63
    n-pentyl acetate 31.43
    transcutol 594.66
    n-heptanol 11.26
    ethylbenzene 32.62
    MIBK 50.94
    2-propoxyethanol 113.86
    tert-butanol 24.89
    MTBE 72.64
    2-butoxyethanol 43.28
    propionic acid 36.07
    o-xylene 30.33
    formic acid 19.83
    diethyl ether 164.95
    m-xylene 34.7
    p-xylene 33.06
    chlorobenzene 87.38
    dimethyl carbonate 77.87
    n-octane 0.93
    formamide 65.33
    cyclopentanone 105.98
    2-pentanone 95.44
    anisole 127.31
    cyclopentyl methyl ether 77.78
    gamma-butyrolactone 151.55
    1-methoxy-2-propanol 93.62
    pyridine 266.89
    3-pentanone 105.35
    furfural 180.64
    n-dodecane 0.83
    diethylene glycol 66.87
    diisopropyl ether 21.63
    tert-amyl alcohol 25.31
    acetylacetone 168.74
    n-hexadecane 0.98
    acetophenone 76.66
    methyl propionate 181.58
    isopentyl acetate 89.47
    trichloroethylene 482.05
    n-nonanol 8.63
    cyclohexanol 15.91
    benzyl alcohol 46.78
    2-ethylhexanol 18.3
    isooctanol 10.24
    dipropyl ether 53.26
    1,2-dichlorobenzene 76.88
    ethyl lactate 29.98
    propylene carbonate 81.43
    n-methylformamide 64.12
    2-pentanol 17.35
    n-pentane 1.52
    1-propoxy-2-propanol 70.99
    1-methoxy-2-propyl acetate 156.43
    2-(2-methoxypropoxy) propanol 73.72
    mesitylene 16.47
    ε-caprolactone 97.57
    p-cymene 15.16
    epichlorohydrin 355.49
    1,1,1-trichloroethane 128.21
    2-aminoethanol 15.86
    morpholine-4-carbaldehyde 128.12
    sulfolane 87.57
    2,2,4-trimethylpentane 1.7
    2-methyltetrahydrofuran 112.81
    n-hexyl acetate 31.57
    isooctane 1.55
    2-(2-butoxyethoxy)ethanol 110.6
    sec-butyl acetate 60.69
    tert-butyl acetate 94.9
    decalin 2.71
    glycerin 16.54
    diglyme 292.77
    acrylic acid 32.9
    isopropyl myristate 19.71
    n-butyric acid 77.2
    acetyl acetate 144.75
    di(2-ethylhexyl) phthalate 19.78
    ethyl propionate 101.31
    nitromethane 226.73
    1,2-diethoxyethane 237.17
    benzonitrile 63.38
    trioctyl phosphate 10.18
    1-bromopropane 84.5
    gamma-valerolactone 189.78
    n-decanol 7.18
    triethyl phosphate 36.13
    4-methyl-2-pentanol 13.64
    propionitrile 83.78
    vinylene carbonate 97.92
    1,1,2-trichlorotrifluoroethane 119.82
    DMS 67.92
    cumene 17.92
    2-octanol 5.91
    2-hexanone 62.18
    octyl acetate 20.8
    limonene 17.98
    1,2-dimethoxyethane 272.17
    ethyl orthosilicate 37.62
    tributyl phosphate 17.84
    diacetone alcohol 62.65
    N,N-dimethylaniline 50.26
    acrylonitrile 114.33
    aniline 73.27
    1,3-propanediol 32.99
    bromobenzene 105.35
    dibromomethane 187.33
    1,1,2,2-tetrachloroethane 303.18
    2-methyl-cyclohexyl acetate 49.06
    tetrabutyl urea 19.3
    diisobutyl methanol 14.73
    2-phenylethanol 48.8
    styrene 51.42
    dioctyl adipate 34.38
    dimethyl sulfate 69.91
    ethyl butyrate 91.68
    methyl lactate 42.55
    butyl lactate 23.49
    diethyl carbonate 65.76
    propanediol butyl ether 24.53
    triethyl orthoformate 64.41
    p-tert-butyltoluene 15.44
    methyl 4-tert-butylbenzoate 47.88
    morpholine 283.27
    tert-butylamine 13.67
    n-dodecanol 6.08
    dimethoxymethane 223.63
    ethylene carbonate 78.2
    cyrene 39.83
    2-ethoxyethyl acetate 102.85
    2-ethylhexyl acetate 67.85
    1,2,4-trichlorobenzene 83.25
    4-methylpyridine 158.76
    dibutyl ether 32.97
    2,6-dimethyl-4-heptanol 14.73
    DEF 107.19
    dimethyl isosorbide 139.13
    tetrachloroethylene 133.43
    eugenol 48.99
    triacetin 55.88
    span 80 38.07
    1,4-butanediol 9.86
    1,1-dichloroethane 154.53
    2-methyl-1-pentanol 27.29
    methyl formate 53.65
    2-methyl-1-butanol 20.52
    n-decane 1.23
    butyronitrile 66.36
    3,7-dimethyl-1-octanol 13.51
    1-chlorooctane 7.6
    1-chlorotetradecane 3.81
    n-nonane 0.99
    undecane 0.98
    tert-butylcyclohexane 2.98
    cyclooctane 1.16
    cyclopentanol 12.78
    tetrahydropyran 165.97
    tert-amyl methyl ether 52.2
    2,5,8-trioxanonane 184.83
    1-hexene 13.98
    2-isopropoxyethanol 55.48
    2,2,2-trifluoroethanol 18.84
    methyl butyrate 103.94

    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