2-Nitroaniline

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  • Identifiers

    CAS number
    88-74-4

    Molecular formula
    C6H6N2O2

    SMILES
    C1=CC=C(C(=C1)N)[N+](=O)[O-]

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 49.43%
    Floral 49.35%
    Grape 47.91%
    Neroli 36.83%
    Odorless 36.15%
    Powdery 32.51%
    Honey 31.75%
    Orange 29.96%
    Fruity 28.89%
    Bitter 26.91%

     

    Flavor
    Odorless 47.09%
    Bitter 43.72%
    Mild 37.1%
    Nutty 25.13%
    Phenolic 24.2%
    Nitrile 21.92%
    Orange flower 21.75%
    Urine 21.68%
    Bread crust 21.23%
    Faint 20.87%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    7.1 (neutral)

    Molecular weight
    138.12 g/mol

    Melting point expt.

    • 160.7 °F (NTP, 1992)
    • 71.0 °C
    • Heat of fusion at melting point = 16.1 kJ/mol
    • 71 °C

    Boiling point

    • 543 °F at 760 mmHg (NTP, 1992)
    • 284 °C

    Flash point

    • 132.89 ˚C est.
    • 335 °F (NTP, 1992)
    • 168 °C

    Solubility expt.

    • less than 1 mg/mL at 70.7 °F (NTP, 1992)
    • Soluble in ethanol; very soluble in ether, acetone, benzene, chloroform
    • Slightly sol in cold water; sol in hot water
    • In water, 1.47X10+3 mg/L at 30 °C
    • Solubility in water, g/100ml at 25 °C: 0.126

  • Synonyms

    • 2-NITROANILINE
    • o-Nitroaniline
    • 88-74-4
    • 2-Nitrobenzenamine
    • Benzenamine, 2-nitro-
    • o-Nitraniline
    • 1-Amino-2-nitrobenzene
    • Fast Orange GR Base
    • Devol Orange B
    • Diazo Fast Orange GR
    • Orange GRS Salt
    • o-Aminonitrobenzene
    • 2-Aminonitrobenzene
    • Aniline, o-nitro-
    • 2-Nitro-phenylamine
    • Fast Orange O Base
    • Fast Orange O Salt
    • Devol Orange Salt B
    • Orthonitroaniline
    • Fast Orange Base GR
    • Fast Orange Base JR
    • Fast Orange GR Salt
    • Fast Orange Salt GR
    • Fast Orange Salt JR
    • Orange Base Ciba II
    • Orange Base Irga II
    • Orange Salt Ciba II
    • Orange Salt Irga II
    • ortho-nitroaniline
    • Azoene Fast Orange GR Salt
    • Azofix Orange GR Salt
    • Natasol Fast Orange GR Salt
    • Azogene Fast Orange GR
    • Hindasol Orange GR Salt
    • Azoic Diazo Component 6
    • Azoene Fast Orange GR Base
    • Hiltonil Fast Orange GR Base
    • Hiltosal Fast Orange GR Salt
    • Brentamine Fast Orange GR Base
    • Brentamine Fast Orange GR Salt
    • C.I. Azoic Diazo Component 6
    • NSC 9796
    • CI Azoic Diazo Component 6
    • CCRIS 2317
    • 2-NITRO-ANILINE
    • DTXSID1025726
    • o-Nitranilin
    • HSDB 1132
    • CI 37025
    • C.I. 37025
    • EINECS 201-855-4
    • 2-Nitro-benzeneamine
    • Aniline, 2-nitro-
    • AI3-02916
    • UNII-2519U0541L
    • NSC-9796
    • NITROANILINE, O-
    • O-NITROANILINE [MI]
    • 2-NITROANILINE [HSDB]
    • DTXCID905726
    • ONA
    • EC 201-855-4
    • 2519U0541L
    • o-nitro aniline
    • 2-nitrophenylamine
    • CAS-88-74-4
    • oNitraniline
    • oNitroaniline
    • 2nitroaniline
    • o-nitro-aniline
    • Aniline, onitro
    • 2Nitrobenzenamine
    • 2-nitro aniline
    • oAminonitrobenzene
    • 2-nitro-anilin
    • 2Aminonitrobenzene
    • 1Amino2nitrobenzene
    • Benzenamine, 2nitro
    • MFCD00007687
    • (2-nitrophenyl)-amine
    • 1-Nitro-2-aminobenzene
    • 2-Nitroaniline, 98%
    • 2-Nitroaniline, 99%
    • 2-Nitroaniline-al-14c
    • (2-nitro-phenyl)-amine
    • WLN: ZR BNW
    • SCHEMBL6000
    • CHEMBL274009
    • SCHEMBL11911292
    • NSC9796
    • BCP05324
    • STR00840
    • Tox21_202371
    • Tox21_303292
    • BDBM50554334
    • STL140693
    • AKOS000119116
    • o-Nitroaniline [UN1661] [Poison]
    • NCGC00091373-01
    • NCGC00091373-02
    • NCGC00257171-01
    • NCGC00259920-01
    • BP-21264
    • DB-057102
    • N0118
    • NS00003098
    • EN300-17394
    • D97708
    • Q2590230
    • Z56924541
    • F2190-0432
    • 38500-40-2

  • Applications

    2-Nitroaniline (CAS 88-74-4) is primarily used as an organic intermediate in the production of azo dyes and pigments; after reduction, it provides access to anilines such as 2-aminophenol for further dye chemistry; it serves as a precursor for colorants used in textiles, printing inks, and coatings and plastics; it is also employed in industrial and specialty chemical synthesis as a starting material for diazo coupling and related reactions in research and manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 70.01
    methanol 96.48
    isopropanol 45.99
    water 0.85
    ethyl acetate 287.24
    n-propanol 54.5
    acetone 560.53
    n-butanol 43.29
    acetonitrile 358.3
    DMF 748.49
    toluene 29.43
    isobutanol 32.3
    1,4-dioxane 330.25
    methyl acetate 384.68
    THF 550.48
    2-butanone 402.97
    n-pentanol 39.71
    sec-butanol 48.81
    n-hexane 2.02
    ethylene glycol 44.99
    NMP 497.5
    cyclohexane 1.97
    DMSO 829.72
    n-butyl acetate 85.48
    n-octanol 27.28
    chloroform 81.39
    n-propyl acetate 101.98
    acetic acid 130.15
    dichloromethane 112.47
    cyclohexanone 216.34
    propylene glycol 41.09
    isopropyl acetate 95.81
    DMAc 467.13
    2-ethoxyethanol 127.94
    isopentanol 39.35
    n-heptane 2.84
    ethyl formate 147.54
    1,2-dichloroethane 152.96
    n-hexanol 45.0
    2-methoxyethanol 257.66
    isobutyl acetate 37.67
    tetrachloromethane 7.42
    n-pentyl acetate 45.21
    transcutol 609.63
    n-heptanol 22.67
    ethylbenzene 16.26
    MIBK 91.04
    2-propoxyethanol 127.83
    tert-butanol 66.18
    MTBE 70.95
    2-butoxyethanol 63.11
    propionic acid 122.7
    o-xylene 22.74
    formic acid 89.14
    diethyl ether 110.18
    m-xylene 21.84
    p-xylene 22.19
    chlorobenzene 57.5
    dimethyl carbonate 132.7
    n-octane 1.33
    formamide 247.52
    cyclopentanone 429.69
    2-pentanone 222.43
    anisole 68.91
    cyclopentyl methyl ether 100.04
    gamma-butyrolactone 522.87
    1-methoxy-2-propanol 166.13
    pyridine 173.84
    3-pentanone 190.35
    furfural 309.43
    n-dodecane 1.62
    diethylene glycol 147.4
    diisopropyl ether 21.2
    tert-amyl alcohol 54.44
    acetylacetone 313.04
    n-hexadecane 1.88
    acetophenone 79.27
    methyl propionate 242.98
    isopentyl acetate 59.83
    trichloroethylene 268.68
    n-nonanol 25.23
    cyclohexanol 36.96
    benzyl alcohol 47.93
    2-ethylhexanol 27.3
    isooctanol 18.75
    dipropyl ether 36.48
    1,2-dichlorobenzene 50.05
    ethyl lactate 61.38
    propylene carbonate 188.59
    n-methylformamide 337.6
    2-pentanol 33.97
    n-pentane 1.87
    1-propoxy-2-propanol 82.06
    1-methoxy-2-propyl acetate 110.27
    2-(2-methoxypropoxy) propanol 95.71
    mesitylene 13.64
    ε-caprolactone 179.01
    p-cymene 13.69
    epichlorohydrin 415.9
    1,1,1-trichloroethane 83.63
    2-aminoethanol 57.04
    morpholine-4-carbaldehyde 352.28
    sulfolane 528.28
    2,2,4-trimethylpentane 2.09
    2-methyltetrahydrofuran 233.74
    n-hexyl acetate 68.06
    isooctane 1.83
    2-(2-butoxyethoxy)ethanol 134.12
    sec-butyl acetate 52.13
    tert-butyl acetate 98.33
    decalin 2.39
    glycerin 78.38
    diglyme 248.45
    acrylic acid 137.96
    isopropyl myristate 28.41
    n-butyric acid 97.48
    acetyl acetate 140.04
    di(2-ethylhexyl) phthalate 26.82
    ethyl propionate 104.63
    nitromethane 803.56
    1,2-diethoxyethane 117.01
    benzonitrile 75.45
    trioctyl phosphate 22.8
    1-bromopropane 49.95
    gamma-valerolactone 386.06
    n-decanol 20.25
    triethyl phosphate 35.79
    4-methyl-2-pentanol 24.18
    propionitrile 139.87
    vinylene carbonate 158.42
    1,1,2-trichlorotrifluoroethane 181.91
    DMS 104.68
    cumene 11.7
    2-octanol 16.18
    2-hexanone 114.5
    octyl acetate 38.09
    limonene 19.83
    1,2-dimethoxyethane 227.89
    ethyl orthosilicate 29.43
    tributyl phosphate 28.68
    diacetone alcohol 135.77
    N,N-dimethylaniline 39.05
    acrylonitrile 234.85
    aniline 48.58
    1,3-propanediol 78.44
    bromobenzene 44.04
    dibromomethane 60.39
    1,1,2,2-tetrachloroethane 168.77
    2-methyl-cyclohexyl acetate 42.5
    tetrabutyl urea 40.95
    diisobutyl methanol 19.48
    2-phenylethanol 52.05
    styrene 20.44
    dioctyl adipate 45.8
    dimethyl sulfate 234.01
    ethyl butyrate 63.86
    methyl lactate 122.59
    butyl lactate 45.04
    diethyl carbonate 49.53
    propanediol butyl ether 76.87
    triethyl orthoformate 41.59
    p-tert-butyltoluene 13.85
    methyl 4-tert-butylbenzoate 64.07
    morpholine 278.66
    tert-butylamine 27.58
    n-dodecanol 15.98
    dimethoxymethane 309.17
    ethylene carbonate 117.24
    cyrene 90.9
    2-ethoxyethyl acetate 95.51
    2-ethylhexyl acetate 46.12
    1,2,4-trichlorobenzene 67.88
    4-methylpyridine 145.37
    dibutyl ether 32.47
    2,6-dimethyl-4-heptanol 19.48
    DEF 232.16
    dimethyl isosorbide 149.3
    tetrachloroethylene 78.48
    eugenol 67.03
    triacetin 87.36
    span 80 61.43
    1,4-butanediol 36.92
    1,1-dichloroethane 112.48
    2-methyl-1-pentanol 35.09
    methyl formate 313.72
    2-methyl-1-butanol 33.9
    n-decane 2.32
    butyronitrile 95.69
    3,7-dimethyl-1-octanol 28.09
    1-chlorooctane 14.65
    1-chlorotetradecane 6.69
    n-nonane 1.93
    undecane 1.95
    tert-butylcyclohexane 2.44
    cyclooctane 0.84
    cyclopentanol 61.7
    tetrahydropyran 167.51
    tert-amyl methyl ether 56.82
    2,5,8-trioxanonane 179.34
    1-hexene 13.07
    2-isopropoxyethanol 74.21
    2,2,2-trifluoroethanol 83.52
    methyl butyrate 128.97

    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