4-Nitroaniline

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  • Identifiers

    CAS number
    100-01-6

    Molecular formula
    C6H6N2O2

    SMILES
    C1=CC(=CC=C1N)[N+](=O)[O-]

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 45.25%
    Floral 41.62%
    Grape 38.57%
    Odorless 37.85%
    Powdery 31.37%
    Neroli 29.78%
    Animal 29.74%
    Honey 29.14%
    Bitter 28.24%
    Phenolic 28.19%

     

    Flavor
    Odorless 45.23%
    Bitter 38.65%
    Mild 38.59%
    Phenolic 30.12%
    Nutty 26.76%
    Faint 23.74%
    Urine 22.8%
    Orange flower 22.1%
    Nitrile 22.05%
    Bread crust 21.3%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    6.64 (neutral)

    Molecular weight
    138.12 g/mol

    Melting point expt.

    • 298 °F (NTP, 1992)
    • 146 °C
    • Heat of fusion at melting point = 21.2 kJ/mol
    • 148 °C
    • 295 °F

    Boiling point

    • 637 °F at 760 mmHg (NTP, 1992)
    • 332 °C (calculated)
    • 332 °C
    • 630 °F

    Flash point

    • 160.51 ˚C est.
    • 390 °F (NTP, 1992)
    • 199 °C
    • 329 °F (OPEN CUP) (MOLTEN SOLID)
    • 199 °C (closed cup)
    • 390 °F

    Solubility expt.

    • less than 0.1 mg/mL at 70 °F (NTP, 1992)
    • Very soluble in methanol; soluble in ethanol, ether, acetone, chloroform, toluene; slightly soluble in benzene, deuterated DMSO
    • 1 g/45 mL boiling water; 1 g/25 mL alcohol; 1 g/30 mL ether
    • 0.08 g/100 g water at 18.5 °C.
    • In water, 390 ppm at 20 °C
    • For more Solubility (Complete) data for 4-NITROANILINE (7 total), please visit the HSDB record page.
    • Solubility in water, g/100ml at 18.5 °C: 0.08
    • 0.08%

  • Synonyms

    • 4-NITROANILINE
    • p-Nitroaniline
    • 100-01-6
    • 4-Nitrobenzenamine
    • p-Aminonitrobenzene
    • p-Nitraniline
    • p-Nitrophenylamine
    • Benzenamine, 4-nitro-
    • 4-Nitraniline
    • 1-Amino-4-nitrobenzene
    • Aniline, p-nitro-
    • para-Nitroaniline
    • Aniline, 4-nitro-
    • Developer P
    • Azoamine Red ZH
    • Nitrazol CF extra
    • Devol Red GG
    • Fast Red P Base
    • Fast Red P Salt
    • Fast Red Base GG
    • Fast Red GG Base
    • Fast Red GG Salt
    • Fast Red MP Base
    • Fast Red Salt GG
    • Diazo Fast Red GG
    • Red 2G Base
    • Fast Red 2G Base
    • Fast Red 2G Salt
    • Fast Red Base 2J
    • Fast Red Salt 2J
    • Azofix Red GG Salt
    • C.I. Developer 17
    • Naphtoelan Red GG Base
    • Azoic Diazo Component 37
    • Paranitroaniline
    • p-Nitroanilina
    • Shinnippon Fast Red GG Base
    • Nitroaniline, p-
    • 4-nitrophenylamine
    • Rcra waste number P077
    • C.I. Azoic Diazo Component 37
    • NSC 9797
    • CCRIS 1184
    • 4-NITRO-ANILINE
    • DTXSID8020961
    • HSDB 1156
    • UNII-1MRQ0QZG7G
    • NCI-C60786
    • C.I. 37035
    • EINECS 202-810-1
    • MFCD00007858
    • 4-Nitrobenzeneamine
    • CHEBI:17064
    • AI3-08926
    • NSC-9797
    • 1MRQ0QZG7G
    • P-NITROANILINE [MI]
    • DTXCID40961
    • 4-NITROANILINE [HSDB]
    • EC 202-810-1
    • NCGC00091426-02
    • 4-Aminonitrobenzene
    • CI Developer 17
    • para-Aminonitrobenzene
    • P-NITROANILINE, (SOLID)
    • P-NITROANILINE, [SOLID]
    • p-Nitroanilina [Polish]
    • paranitronaniline
    • p-nitro aniline
    • PNA (VAN)
    • 4-NITRO-PHENYLAMINE
    • Azoamine Red 2H
    • CI Azoic Diazo Component 37
    • RCRA waste no. P077
    • NITROANILINE (PARA NITROANILINE) (P-NITROANILINE)
    • NITROANILINE (PARA NITROANILINE) {P-NITROANILINE}
    • pNitraniline
    • pNitroanilina
    • pNitroaniline
    • CI 37035
    • 4nitroaniline
    • 4Nitraniline
    • p-nitro-aniline
    • para-nitroanilin
    • pNitrophenylamine
    • Aniline, pnitro
    • 4Nitrobenzenamine
    • 4-nitro aniline
    • pAminonitrobenzene
    • Aniline, 4nitro
    • 1Amino4nitrobenzene
    • paraAminonitrobenzene
    • Benzenamine, 4nitro
    • p-Nitroaniline, solid
    • (4-nitrophenyl)-amine
    • 4-Nitroaniline Standard
    • 4-amino-1-nitrobenzene
    • 4-Nitroaniline, 99%
    • FAST RED IG BASE
    • WLN: ZR DNW
    • 4-Nitroaniline, crystalline
    • 4-Nitroaniline, >=99%
    • NCIOpen2_002864
    • SCHEMBL16451
    • MLS002454441
    • CHEMBL14282
    • PARANITROANILINE, SOLID
    • Benzenamine, 4-nitro-(9CI)
    • p-Nitroaniline (ACGIH:OSHA)
    • SCHEMBL10163408
    • NSC9797
    • HMS3039B17
    • 4-Nitroaniline, analytical standard
    • STR00350
    • Tox21_400031
    • STK301653
    • AKOS000119131
    • AKOS025293369
    • FN34321
    • p-Nitroaniline [UN1661] [Poison]
    • p-Nitroaniline; p-Nitrophenylamine; 1-Amino-4-nitrobenzene; 4-Nitrobenzenamine
    • NCGC00091426-01
    • NCGC00091426-03
    • CAS-100-01-6
    • PD150625
    • SMR001372024
    • N0119
    • NS00005117

  • Applications

    4-Nitroaniline (CAS 100-01-6) is primarily used as an intermediate in the manufacture of azo dyes and related pigments. Upon reduction of the nitro group, it yields p-phenylenediamine, a key building block for rubber chemicals and hair dye formulations. It can also be converted to p-aminophenol, a pharmaceutical intermediate used in the synthesis of paracetamol. More broadly, it serves as a starting material for organic synthesis of dye intermediates and other specialty chemicals in industrial settings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.32
    methanol 21.47
    isopropanol 8.33
    water 0.32
    ethyl acetate 57.02
    n-propanol 9.01
    acetone 139.06
    n-butanol 7.77
    acetonitrile 51.77
    DMF 238.47
    toluene 1.46
    isobutanol 5.59
    1,4-dioxane 94.62
    methyl acetate 102.25
    THF 151.48
    2-butanone 99.09
    n-pentanol 8.13
    sec-butanol 7.15
    n-hexane 0.09
    ethylene glycol 11.98
    NMP 427.66
    cyclohexane 0.05
    DMSO 254.85
    n-butyl acetate 37.95
    n-octanol 8.59
    chloroform 4.03
    n-propyl acetate 38.58
    acetic acid 76.47
    dichloromethane 12.6
    cyclohexanone 60.66
    propylene glycol 12.02
    isopropyl acetate 31.45
    DMAc 272.35
    2-ethoxyethanol 45.71
    isopentanol 9.0
    n-heptane 0.34
    ethyl formate 42.72
    1,2-dichloroethane 15.88
    n-hexanol 10.91
    2-methoxyethanol 69.39
    isobutyl acetate 17.33
    tetrachloromethane 0.64
    n-pentyl acetate 23.68
    transcutol 331.33
    n-heptanol 8.7
    ethylbenzene 1.75
    MIBK 25.8
    2-propoxyethanol 48.61
    tert-butanol 15.61
    MTBE 17.12
    2-butoxyethanol 34.29
    propionic acid 38.64
    o-xylene 2.42
    formic acid 49.23
    diethyl ether 12.9
    m-xylene 1.8
    p-xylene 3.37
    chlorobenzene 6.58
    dimethyl carbonate 45.07
    n-octane 0.15
    formamide 115.14
    cyclopentanone 168.69
    2-pentanone 46.8
    anisole 23.26
    cyclopentyl methyl ether 20.65
    gamma-butyrolactone 249.46
    1-methoxy-2-propanol 43.61
    pyridine 46.82
    3-pentanone 36.34
    furfural 180.62
    n-dodecane 0.25
    diethylene glycol 55.15
    diisopropyl ether 3.41
    tert-amyl alcohol 13.14
    acetylacetone 111.0
    n-hexadecane 0.3
    acetophenone 39.37
    methyl propionate 53.16
    isopentyl acetate 33.33
    trichloroethylene 37.27
    n-nonanol 8.76
    cyclohexanol 5.47
    benzyl alcohol 17.09
    2-ethylhexanol 8.21
    isooctanol 7.09
    dipropyl ether 9.53
    1,2-dichlorobenzene 9.64
    ethyl lactate 26.09
    propylene carbonate 100.44
    n-methylformamide 91.54
    2-pentanol 5.04
    n-pentane 0.07
    1-propoxy-2-propanol 34.04
    1-methoxy-2-propyl acetate 59.94
    2-(2-methoxypropoxy) propanol 59.83
    mesitylene 1.6
    ε-caprolactone 79.53
    p-cymene 3.99
    epichlorohydrin 159.88
    1,1,1-trichloroethane 7.32
    2-aminoethanol 14.5
    morpholine-4-carbaldehyde 254.63
    sulfolane 271.91
    2,2,4-trimethylpentane 0.2
    2-methyltetrahydrofuran 63.71
    n-hexyl acetate 35.6
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 76.87
    sec-butyl acetate 22.91
    tert-butyl acetate 42.34
    decalin 0.22
    glycerin 30.14
    diglyme 155.52
    acrylic acid 54.75
    isopropyl myristate 13.28
    n-butyric acid 30.35
    acetyl acetate 58.79
    di(2-ethylhexyl) phthalate 19.64
    ethyl propionate 31.21
    nitromethane 336.13
    1,2-diethoxyethane 50.77
    benzonitrile 25.14
    trioctyl phosphate 12.38
    1-bromopropane 2.32
    gamma-valerolactone 215.97
    n-decanol 6.65
    triethyl phosphate 19.56
    4-methyl-2-pentanol 4.63
    propionitrile 19.33
    vinylene carbonate 74.66
    1,1,2-trichlorotrifluoroethane 91.06
    DMS 60.67
    cumene 2.12
    2-octanol 5.2
    2-hexanone 37.27
    octyl acetate 20.02
    limonene 5.89
    1,2-dimethoxyethane 83.15
    ethyl orthosilicate 15.04
    tributyl phosphate 16.4
    diacetone alcohol 58.51
    N,N-dimethylaniline 15.05
    acrylonitrile 44.89
    aniline 8.3
    1,3-propanediol 21.98
    bromobenzene 3.94
    dibromomethane 3.16
    1,1,2,2-tetrachloroethane 20.63
    2-methyl-cyclohexyl acetate 25.96
    tetrabutyl urea 23.13
    diisobutyl methanol 5.32
    2-phenylethanol 22.03
    styrene 2.39
    dioctyl adipate 29.7
    dimethyl sulfate 106.22
    ethyl butyrate 28.43
    methyl lactate 41.51
    butyl lactate 23.23
    diethyl carbonate 24.37
    propanediol butyl ether 40.59
    triethyl orthoformate 20.82
    p-tert-butyltoluene 3.82
    methyl 4-tert-butylbenzoate 42.53
    morpholine 76.07
    tert-butylamine 4.46
    n-dodecanol 4.91
    dimethoxymethane 70.46
    ethylene carbonate 51.57
    cyrene 72.76
    2-ethoxyethyl acetate 65.24
    2-ethylhexyl acetate 23.61
    1,2,4-trichlorobenzene 18.5
    4-methylpyridine 31.67
    dibutyl ether 9.98
    2,6-dimethyl-4-heptanol 5.32
    DEF 68.84
    dimethyl isosorbide 107.61
    tetrachloroethylene 10.74
    eugenol 38.22
    triacetin 71.4
    span 80 36.74
    1,4-butanediol 10.77
    1,1-dichloroethane 7.53
    2-methyl-1-pentanol 9.44
    methyl formate 99.6
    2-methyl-1-butanol 7.41
    n-decane 0.34
    butyronitrile 14.3
    3,7-dimethyl-1-octanol 8.28
    1-chlorooctane 2.77
    1-chlorotetradecane 1.42
    n-nonane 0.25
    undecane 0.29
    tert-butylcyclohexane 0.27
    cyclooctane 0.04
    cyclopentanol 13.33
    tetrahydropyran 22.34
    tert-amyl methyl ether 13.42
    2,5,8-trioxanonane 116.0
    1-hexene 0.7
    2-isopropoxyethanol 32.35
    2,2,2-trifluoroethanol 43.1
    methyl butyrate 41.56

    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