4-Nitro-1,2-phenylenediamine

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  • Identifiers

    CAS number
    99-56-9

    Molecular formula
    C6H7N3O2

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.74%
    Bitter 22.43%
    Grape 21.93%
    Burnt 21.79%
    Meaty 20.53%
    Sweet 20.27%
    Savory 20.17%
    Animal 19.72%
    Cooked 19.0%
    Milky 16.49%

     

    Flavor
    Bitter 53.95%
    Odorless 49.73%
    Mild 35.9%
    Nitrile 21.27%
    Orange flower 20.68%
    Bread crust 20.55%
    Very strong 20.33%
    Yeast 20.28%
    Urine 20.15%
    Sweet-like 20.14%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    6.06 (neutral)

    Molecular weight
    153.14 g/mol

    Melting point expt.

    • 390 to 394 °F (NTP, 1992)
    • 199.5 °C
    • 201 °C

    Flash point

    • 184.0 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 68.9 °F (NTP, 1992)
    • Soluble in acid
    • Sparingly sol in water; sol in aq soln of hydrochloric acid
    • Solubility in water: poor

  • Synonyms

    • 4-Nitro-o-phenylenediamine
    • 99-56-9
    • 4-Nitro-1,2-phenylenediamine
    • 1,2-Diamino-4-nitrobenzene
    • 2-Amino-4-nitroaniline
    • 4-Nitro-1,2-diaminobenzene
    • p-Nitro-o-phenylenediamine
    • 3,4-Diaminonitrobenzene
    • 1,2-Benzenediamine, 4-nitro-
    • 4-Nitro-1,2-benzenediamine
    • 4-Nopd
    • 4-Nop
    • 4-N-o-Pda
    • NCI-C03941
    • 4NDB
    • O-PHENYLENEDIAMINE, 4-NITRO-
    • C.I. 76020
    • DTXSID9020958
    • 5A9AX7Y0TT
    • CI 76020
    • NSC-5378
    • DTXCID30958
    • CHEBI:67116
    • RefChem:855316
    • 202-766-3
    • 4-nitrobenzene-1,2-diamine
    • 4-Nitrophenylenediamine
    • 4-NO
    • 4-Nitro-o-phenylene-diamine
    • MFCD00007724
    • Nitro-o-phenylenediamine
    • NSC 5378
    • 4-Nitro-1,2-fenylendiamin
    • p-nitro-o-phenylendiamine
    • CAS-99-56-9
    • 4-Nitro-para-phenylenediamine
    • CCRIS 451
    • HSDB 2895
    • EINECS 202-766-3
    • 4-Nitro-1,2-fenylendiamin [Czech]
    • UNII-5A9AX7Y0TT
    • BRN 0608106
    • 4-nitro-ortho-phenylenediamine
    • AI3-52605
    • 4-nitrobenzene-1
    • 2-amino-5-nitroaniline
    • 4-nitrophenylene diamine
    • 3,4-diamino-nitrobenzene
    • WLN: ZR BZ DNW
    • 2-amino-4-nitrophenylamine
    • 4-nitro-o-phenylene diamine
    • aniline, 2-amino-4-nitro-
    • SCHEMBL78293
    • 4-13-00-00075 (Beilstein Handbook Reference)
    • 4-nitro 1,2-phenylenediamine
    • 4-nitro-1,2-diamino-benzene
    • 4-Nitro-benzene-1,2-diamine
    • CHEMBL433721
    • 4-nitro 1,2-phenylene diamine
    • SCHEMBL29353815
    • (2-amino-5-nitro-phenyl)-amine
    • NSC5378
    • 4-Nitro-o-phenylenediamine, 98%
    • ALBB-021305
    • Tox21_202313
    • Tox21_302811
    • BBL016368
    • MSK000721
    • SBB007571
    • STK317795
    • AKOS000119818
    • AC-2759
    • CCG-325544
    • CS-W007627
    • GS-3013
    • 4-NITRO-O-PHENYLENEDIAMINE [MI]
    • NCGC00091593-01
    • NCGC00091593-02
    • NCGC00091593-03
    • NCGC00256320-01
    • NCGC00259862-01
    • 1,2-DIAMINO-4-NITROBENZENE [IARC]
    • DB-028981
    • 4-NITRO-O-PHENYLENEDIAMINE [WHO-DD]
    • D0103
    • NS00013892
    • O-PHENYLENEDIAMINE, 4-NITRO- [HSDB]
    • ST45061383
    • EN300-19619
    • C19384
    • D77683
    • F077317
    • Q5649571
    • F0001-2335
    • Z104474480
    • InChI=1/C6H7N3O2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H,7-8H
    • 99-56-9

  • Applications

    4-Nitro-1,2-phenylenediamine (CAS 99-56-9) is primarily used as an intermediate in the production of dyes and pigments, particularly azo dye chemistry, and as a building block for specialty colorants and polymer coatings. It also serves as a precursor for heterocyclic compounds such as benzimidazole derivatives and related materials used in advanced polymers. In research and industrial settings it is evaluated as a starting material for additional organic transformations and as a reagent in formulation work, with use governed by local regulations and formulation requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.47
    methanol 6.49
    isopropanol 2.08
    water 0.41
    ethyl acetate 10.73
    n-propanol 1.89
    acetone 63.47
    n-butanol 1.39
    acetonitrile 12.8
    DMF 61.39
    toluene 0.14
    isobutanol 1.23
    1,4-dioxane 16.83
    methyl acetate 30.12
    THF 48.24
    2-butanone 45.73
    n-pentanol 1.47
    sec-butanol 1.6
    n-hexane 0.02
    ethylene glycol 4.94
    NMP 96.73
    cyclohexane 0.01
    DMSO 108.68
    n-butyl acetate 6.87
    n-octanol 1.29
    chloroform 0.3
    n-propyl acetate 6.08
    acetic acid 20.6
    dichloromethane 0.9
    cyclohexanone 10.35
    propylene glycol 3.91
    isopropyl acetate 5.18
    DMAc 118.85
    2-ethoxyethanol 14.82
    isopentanol 1.82
    n-heptane 0.08
    ethyl formate 12.58
    1,2-dichloroethane 1.3
    n-hexanol 2.21
    2-methoxyethanol 23.62
    isobutyl acetate 2.56
    tetrachloromethane 0.17
    n-pentyl acetate 3.66
    transcutol 36.3
    n-heptanol 2.03
    ethylbenzene 0.18
    MIBK 4.72
    2-propoxyethanol 15.01
    tert-butanol 4.4
    MTBE 3.3
    2-butoxyethanol 10.44
    propionic acid 8.16
    o-xylene 0.28
    formic acid 20.94
    diethyl ether 1.97
    m-xylene 0.19
    p-xylene 0.43
    chlorobenzene 0.47
    dimethyl carbonate 9.31
    n-octane 0.04
    formamide 49.07
    cyclopentanone 41.67
    2-pentanone 10.38
    anisole 3.51
    cyclopentyl methyl ether 2.59
    gamma-butyrolactone 61.95
    1-methoxy-2-propanol 11.83
    pyridine 6.4
    3-pentanone 8.21
    furfural 41.75
    n-dodecane 0.04
    diethylene glycol 19.45
    diisopropyl ether 0.53
    tert-amyl alcohol 3.16
    acetylacetone 27.13
    n-hexadecane 0.05
    acetophenone 7.41
    methyl propionate 10.42
    isopentyl acetate 6.45
    trichloroethylene 2.39
    n-nonanol 1.44
    cyclohexanol 0.67
    benzyl alcohol 2.81
    2-ethylhexanol 1.58
    isooctanol 1.63
    dipropyl ether 2.0
    1,2-dichlorobenzene 0.86
    ethyl lactate 6.19
    propylene carbonate 20.93
    n-methylformamide 27.12
    2-pentanol 0.84
    n-pentane 0.02
    1-propoxy-2-propanol 8.66
    1-methoxy-2-propyl acetate 13.28
    2-(2-methoxypropoxy) propanol 13.97
    mesitylene 0.19
    ε-caprolactone 13.78
    p-cymene 0.7
    epichlorohydrin 31.1
    1,1,1-trichloroethane 0.84
    2-aminoethanol 5.28
    morpholine-4-carbaldehyde 50.3
    sulfolane 61.29
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 12.13
    n-hexyl acetate 4.63
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 15.82
    sec-butyl acetate 3.49
    tert-butyl acetate 7.96
    decalin 0.03
    glycerin 10.65
    diglyme 36.29
    acrylic acid 11.65
    isopropyl myristate 2.13
    n-butyric acid 6.35
    acetyl acetate 10.54
    di(2-ethylhexyl) phthalate 4.24
    ethyl propionate 5.28
    nitromethane 104.69
    1,2-diethoxyethane 7.48
    benzonitrile 2.93
    trioctyl phosphate 2.62
    1-bromopropane 0.24
    gamma-valerolactone 50.94
    n-decanol 1.12
    triethyl phosphate 5.17
    4-methyl-2-pentanol 0.88
    propionitrile 3.75
    vinylene carbonate 13.87
    1,1,2-trichlorotrifluoroethane 20.5
    DMS 8.87
    cumene 0.27
    2-octanol 0.96
    2-hexanone 6.8
    octyl acetate 3.24
    limonene 0.91
    1,2-dimethoxyethane 26.26
    ethyl orthosilicate 3.83
    tributyl phosphate 3.07
    diacetone alcohol 14.71
    N,N-dimethylaniline 2.42
    acrylonitrile 7.86
    aniline 0.9
    1,3-propanediol 7.03
    bromobenzene 0.26
    dibromomethane 0.3
    1,1,2,2-tetrachloroethane 1.64
    2-methyl-cyclohexyl acetate 5.59
    tetrabutyl urea 5.18
    diisobutyl methanol 1.19
    2-phenylethanol 4.58
    styrene 0.23
    dioctyl adipate 5.07
    dimethyl sulfate 25.54
    ethyl butyrate 5.88
    methyl lactate 10.79
    butyl lactate 4.75
    diethyl carbonate 5.46
    propanediol butyl ether 7.63
    triethyl orthoformate 4.69
    p-tert-butyltoluene 0.67
    methyl 4-tert-butylbenzoate 9.79
    morpholine 14.12
    tert-butylamine 1.05
    n-dodecanol 0.83
    dimethoxymethane 19.72
    ethylene carbonate 10.06
    cyrene 21.17
    2-ethoxyethyl acetate 11.32
    2-ethylhexyl acetate 4.36
    1,2,4-trichlorobenzene 1.64
    4-methylpyridine 3.71
    dibutyl ether 1.24
    2,6-dimethyl-4-heptanol 1.19
    DEF 12.87
    dimethyl isosorbide 29.03
    tetrachloroethylene 1.19
    eugenol 9.35
    triacetin 11.3
    span 80 7.35
    1,4-butanediol 3.44
    1,1-dichloroethane 0.63
    2-methyl-1-pentanol 1.78
    methyl formate 31.73
    2-methyl-1-butanol 1.44
    n-decane 0.06
    butyronitrile 2.57
    3,7-dimethyl-1-octanol 1.42
    1-chlorooctane 0.3
    1-chlorotetradecane 0.19
    n-nonane 0.04
    undecane 0.05
    tert-butylcyclohexane 0.04
    cyclooctane 0.01
    cyclopentanol 2.12
    tetrahydropyran 2.67
    tert-amyl methyl ether 2.5
    2,5,8-trioxanonane 29.19
    1-hexene 0.11
    2-isopropoxyethanol 8.73
    2,2,2-trifluoroethanol 13.92
    methyl butyrate 7.88

    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