2-Nitro-4-phenylenediamine

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  • Identifiers

    CAS number
    5307-14-2

    Molecular formula
    C6H7N3O2

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 49.36%
    Grape 36.2%
    Sweet 29.8%
    Animal 23.79%
    Bitter 22.99%
    Fruity 21.89%
    Neroli 21.73%
    Fatty 20.92%
    Powdery 20.81%
    Floral 20.68%

     

    Flavor
    Bitter 52.01%
    Odorless 49.7%
    Mild 36.58%
    Nitrile 21.21%
    Orange flower 20.78%
    Bread crust 20.53%
    Very strong 20.21%
    Yeast 20.19%
    Roasted peanuts 20.02%
    Urine 20.01%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    6.79 (neutral)

    Molecular weight
    153.14 g/mol

    Melting point expt.

    • 279 °F (NTP, 1992)
    • 140 °C
    • 137 °C

    Flash point

    • 171.16 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 72 °F (NTP, 1992)
    • Slightly sol in water (0.18% w/w); ethanol, polar organic compounds and benzene; soluble in acetone and diethyl ether
    • Solubility in water, g/100ml: 0.18

  • Synonyms

    • 2-Nitro-4-phenylenediamine
    • RefChem:88700
    • 5307-14-2
    • 2-nitrobenzene-1,4-diamine
    • 2-Nitro-1,4-phenylenediamine
    • 2-NITRO-P-PHENYLENEDIAMINE
    • 1,4-Diamino-2-nitrobenzene
    • 1,4-Benzenediamine, 2-nitro-
    • 2,5-Diaminonitrobenzene
    • 2-Nitro-1,4-benzenediamine
    • o-Nitro-p-phenylenediamine
    • Durafur Brown
    • Fouramine 2R
    • Ursol Brown RR
    • Durafur Brown 2R
    • 4-Amino-2-nitroaniline
    • 2-NPPD
    • Zoba Brown RR
    • Fourrine 36
    • Nitro-p-phenylenediamine
    • 2-Nitro-1,4-diaminobenzene
    • Fourrine Brown 2R
    • Oxidation base 22
    • Dye GS
    • 2-N-p-PDA
    • 2-Nitro-4-aminoaniline
    • p-Phenylenediamine, 2-nitro-
    • C.I. Oxidation Base 22
    • 2-Nitrol-p-phenylenediamine
    • NCI-C02222
    • MFCD00007903
    • C.I. 76070
    • 1,4-Diaminonitrobenzol
    • 2NDB
    • CI 76070
    • NSC 5377
    • DTXSID4020957
    • PV83F3C01Q
    • NSC-5377
    • NCGC00091278-03
    • CI Oxidation Base 22
    • SKF-49539; Retigabine Related; NPDA
    • CCRIS 452
    • 2-Nitrol-para-phenylenediamine
    • HSDB 4098
    • 1,4-Diaminonitrobenzol [German]
    • EINECS 226-164-5
    • BRN 2210195
    • UNII-PV83F3C01Q
    • 2-Nitro-para-phenylenediamine
    • AI3-52604
    • SCHEMBL78083
    • 2-Nitro-1.4-diaminobenzene
    • 3-13-00-00271 (Beilstein Handbook Reference)
    • DTXCID00957
    • 2-Nitro-benzene-1,4-diamine
    • 2-nitro-benzene-1,4-diarnine
    • CHEMBL353971
    • SCHEMBL8317335
    • SCHEMBL9793637
    • SCHEMBL11496559
    • SCHEMBL29358067
    • CHEBI:76394
    • NSC5377
    • STR08741
    • Tox21_400026
    • SBB064230
    • NITRO-P-PHENYLENEDIAMINE, 2-
    • 2-Nitro-1,4-phenylenediamine, 95%
    • AKOS000120413
    • CS-W018077
    • FN38678
    • NCGC00091278-01
    • NCGC00091278-02
    • NCGC00091278-04
    • AC-11799
    • AC-31742
    • BP-12513
    • SY005815
    • 2-NITRO-P-PHENYLENEDIAMINE [HSDB]
    • CAS-5307-14-2
    • DB-052251
    • A7730
    • C.I.-76070
    • D0105
    • NS00004859
    • ST51040055
    • EN300-17154
    • C19385
    • D70573
    • F078861
    • Q26840737
    • Z56895723
    • F0001-1368
    • 2-Nitro-1,4-phenylenediamine, technical, >=95.0% (NT)
    • 5307-14-2

  • Applications

    2-Nitro-4-phenylenediamine is principally used as an intermediate in the synthesis of azo dyes and related pigments. It is employed to produce colorants for textiles and leather, as well as for coatings and printing inks, by forming chromophores through diazotization or coupling reactions. The compound also serves as a building block for other aromatic amine-based colorants and specialty dyes used in plastics and polymers. In industrial practice, it may be evaluated for research and development programs seeking new dye chemistries or pigment precursors. Overall, its role is primarily as a dye intermediate rather than a finished product, and its use is governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.03
    methanol 34.39
    isopropanol 8.81
    water 1.56
    ethyl acetate 48.68
    n-propanol 13.17
    acetone 200.38
    n-butanol 9.3
    acetonitrile 74.73
    DMF 265.6
    toluene 0.99
    isobutanol 6.44
    1,4-dioxane 87.17
    methyl acetate 69.45
    THF 455.43
    2-butanone 113.31
    n-pentanol 8.51
    sec-butanol 7.24
    n-hexane 0.17
    ethylene glycol 17.36
    NMP 86.71
    cyclohexane 0.07
    DMSO 490.98
    n-butyl acetate 18.1
    n-octanol 6.36
    chloroform 7.67
    n-propyl acetate 17.67
    acetic acid 15.19
    dichloromethane 10.85
    cyclohexanone 44.3
    propylene glycol 10.65
    isopropyl acetate 15.24
    DMAc 199.01
    2-ethoxyethanol 39.07
    isopentanol 7.17
    n-heptane 0.3
    ethyl formate 51.44
    1,2-dichloroethane 15.04
    n-hexanol 11.34
    2-methoxyethanol 80.87
    isobutyl acetate 6.1
    tetrachloromethane 1.79
    n-pentyl acetate 9.27
    transcutol 23.98
    n-heptanol 7.34
    ethylbenzene 1.46
    MIBK 18.1
    2-propoxyethanol 45.4
    tert-butanol 11.5
    MTBE 9.22
    2-butoxyethanol 21.93
    propionic acid 13.34
    o-xylene 1.37
    formic acid 27.39
    diethyl ether 10.06
    m-xylene 1.34
    p-xylene 2.18
    chlorobenzene 3.45
    dimethyl carbonate 30.73
    n-octane 0.19
    formamide 61.56
    cyclopentanone 169.77
    2-pentanone 54.41
    anisole 12.71
    cyclopentyl methyl ether 17.52
    gamma-butyrolactone 156.41
    1-methoxy-2-propanol 39.54
    pyridine 23.62
    3-pentanone 32.24
    furfural 85.38
    n-dodecane 0.19
    diethylene glycol 49.9
    diisopropyl ether 1.57
    tert-amyl alcohol 9.57
    acetylacetone 84.11
    n-hexadecane 0.22
    acetophenone 16.03
    methyl propionate 45.33
    isopentyl acetate 12.47
    trichloroethylene 23.43
    n-nonanol 5.94
    cyclohexanol 3.24
    benzyl alcohol 9.56
    2-ethylhexanol 5.96
    isooctanol 5.34
    dipropyl ether 6.52
    1,2-dichlorobenzene 4.66
    ethyl lactate 13.59
    propylene carbonate 36.29
    n-methylformamide 101.06
    2-pentanol 3.88
    n-pentane 0.09
    1-propoxy-2-propanol 23.5
    1-methoxy-2-propyl acetate 25.51
    2-(2-methoxypropoxy) propanol 19.85
    mesitylene 1.07
    ε-caprolactone 28.99
    p-cymene 2.25
    epichlorohydrin 140.76
    1,1,1-trichloroethane 7.75
    2-aminoethanol 18.13
    morpholine-4-carbaldehyde 82.14
    sulfolane 137.81
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 54.17
    n-hexyl acetate 11.39
    isooctane 0.13
    2-(2-butoxyethoxy)ethanol 23.12
    sec-butyl acetate 7.5
    tert-butyl acetate 15.22
    decalin 0.17
    glycerin 24.4
    diglyme 50.01
    acrylic acid 13.94
    isopropyl myristate 4.56
    n-butyric acid 16.88
    acetyl acetate 20.02
    di(2-ethylhexyl) phthalate 6.31
    ethyl propionate 19.98
    nitromethane 174.89
    1,2-diethoxyethane 11.4
    benzonitrile 11.1
    trioctyl phosphate 5.64
    1-bromopropane 3.57
    gamma-valerolactone 128.64
    n-decanol 4.61
    triethyl phosphate 7.54
    4-methyl-2-pentanol 3.07
    propionitrile 24.45
    vinylene carbonate 26.36
    1,1,2-trichlorotrifluoroethane 48.45
    DMS 13.49
    cumene 1.45
    2-octanol 4.06
    2-hexanone 28.02
    octyl acetate 7.22
    limonene 2.75
    1,2-dimethoxyethane 101.52
    ethyl orthosilicate 5.89
    tributyl phosphate 5.74
    diacetone alcohol 30.81
    N,N-dimethylaniline 7.22
    acrylonitrile 41.9
    aniline 3.96
    1,3-propanediol 24.11
    bromobenzene 2.5
    dibromomethane 4.99
    1,1,2,2-tetrachloroethane 16.82
    2-methyl-cyclohexyl acetate 8.82
    tetrabutyl urea 10.5
    diisobutyl methanol 3.44
    2-phenylethanol 13.56
    styrene 1.55
    dioctyl adipate 7.31
    dimethyl sulfate 66.6
    ethyl butyrate 13.99
    methyl lactate 26.56
    butyl lactate 9.38
    diethyl carbonate 9.82
    propanediol butyl ether 14.55
    triethyl orthoformate 8.17
    p-tert-butyltoluene 2.11
    methyl 4-tert-butylbenzoate 14.57
    morpholine 63.84
    tert-butylamine 3.3
    n-dodecanol 3.32
    dimethoxymethane 114.83
    ethylene carbonate 21.0
    cyrene 25.55
    2-ethoxyethyl acetate 15.64
    2-ethylhexyl acetate 8.54
    1,2,4-trichlorobenzene 6.0
    4-methylpyridine 18.45
    dibutyl ether 4.06
    2,6-dimethyl-4-heptanol 3.44
    DEF 44.57
    dimethyl isosorbide 38.87
    tetrachloroethylene 9.43
    eugenol 17.87
    triacetin 10.77
    span 80 11.6
    1,4-butanediol 11.94
    1,1-dichloroethane 8.05
    2-methyl-1-pentanol 6.47
    methyl formate 122.01
    2-methyl-1-butanol 6.21
    n-decane 0.29
    butyronitrile 20.43
    3,7-dimethyl-1-octanol 5.25
    1-chlorooctane 2.02
    1-chlorotetradecane 0.86
    n-nonane 0.24
    undecane 0.24
    tert-butylcyclohexane 0.21
    cyclooctane 0.05
    cyclopentanol 10.54
    tetrahydropyran 21.29
    tert-amyl methyl ether 7.01
    2,5,8-trioxanonane 35.63
    1-hexene 1.08
    2-isopropoxyethanol 19.41
    2,2,2-trifluoroethanol 17.74
    methyl butyrate 30.26

    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