Picramic Acid

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  • Identifiers

    CAS number
    96-91-3

    Molecular formula
    C6H5N3O5

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

    Safety labels

    Explosive
    Explosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 65.3%
    Sweet 37.21%
    Bitter 23.4%
    Milky 23.03%
    Vanilla 21.92%
    Burnt 21.38%
    Powdery 21.11%
    Creamy 20.16%
    Musk 19.16%
    Fatty 19.04%

     

    Flavor
    Bitter 66.72%
    Odorless 55.64%
    Mild 31.01%
    Very mild 24.18%
    Bland 23.97%
    Sweet-like 21.17%
    Nitrile 20.96%
    Yeast 20.26%
    Bread crust 20.17%
    Very strong 19.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    7.79 (neutral)

    Molecular weight
    199.12 g/mol

    Melting point expt.

    • 336 °F (NTP, 1992)
    • 169 °C

    Flash point

    • 186.55 ˚C est.
    • 410 °F (NTP, 1992)
    • 210 °C

    Solubility expt.

    • less than 1 mg/mL at 68.9 °F (NTP, 1992)
    • @ 22-25 °C, 0.065 g dissolves in 100 ml H2O
    • More sol in hot water than in cold water
    • Soluble in benzene & ether
    • Moderately sol in alc; sol in glacial acetic acid
    • Sol in aniline

  • Synonyms

    • 2-Amino-4,6-dinitrophenol
    • Picramic acid
    • 96-91-3
    • Fourrine 4R
    • Fourrine 93
    • Furro 4R
    • Acide picramique
    • Oxidation Base 21
    • Zoba 4R
    • 2,4-Dinitro-6-aminophenol
    • C.I. Oxidation Base 21
    • CI Oxidation Base 21
    • 1-Amino-2-hydroxy-3,5-dinitrobenzene
    • 5VDQ7GK8L3
    • CI 76540
    • DTXSID5024479
    • NSC-36939
    • DTXCID904479
    • C.I. 76540
    • 1-AMINO-3,5-DINITRO-2-HYDROXYBENZENE
    • RefChem:174178
    • 202-544-6
    • 6-Amino-2,4-dinitrophenol
    • Phenol, 2-amino-4,6-dinitro-
    • 4,6-DINITRO-2-AMINOPHENOL
    • NSC 36939
    • Acide picramique [French]
    • CCRIS 1003
    • HSDB 4319
    • EINECS 202-544-6
    • UN3317
    • UNII-5VDQ7GK8L3
    • BRN 0989416
    • Pikraminsaure
    • 2-amino-4,6-dinitro-phenol
    • AI3-08922
    • PICRAMIC ACID [MI]
    • SCHEMBL18124
    • PICRAMIC ACID [HSDB]
    • 4,6-dinitro-2-amino-phenol
    • 4-13-00-00909 (Beilstein Handbook Reference)
    • 2-azanyl-4,6-dinitro-phenol
    • CHEMBL3183248
    • SCHEMBL29375698
    • NSC4861
    • BB_SC-01516
    • NSC-4861
    • NSC36939
    • Tox21_202887
    • BBL028138
    • EBC-03996
    • SBB058601
    • STK711606
    • AKOS000120580
    • AMINO-4,6-DINITROPHENOL, 2-
    • CAS-96-91-3
    • NCGC00260433-01
    • AC-11460
    • VS-08677
    • DB-020415
    • ST4032788
    • D0813
    • NS00006370
    • EN300-17467
    • G30676
    • 070A534
    • A845654
    • Q283711
    • 2-Amino-4,6-dinitrophenol (wet with ~20% of water)
    • Z56943480
    • 2-Amino-4,6-Dinitrophenol, wetted with not <20% water by mass
    • 2-Amino-4,6-Dinitrophenol, wetted with not <20% water by mass [UN3317] [Flammable solid]
    • 96-91-3

  • Applications

    Picramic acid (CAS 96-91-3) is primarily used as an intermediate in the synthesis of nitro-aromatic dyes and pigment precursors, enabling the formation of azo dyes via diazo coupling; it also serves as a specialty colorant precursor for coatings and inks, where its nitro and amino groups contribute to color development. In analytical and research contexts, it is used as a reagent or starting material for preparing nitroaromatic compounds and other synthetic intermediates; it may appear in laboratory-scale syntheses under appropriate handling and regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 20.46
    methanol 25.85
    isopropanol 11.74
    water 0.88
    ethyl acetate 30.45
    n-propanol 11.54
    acetone 94.44
    n-butanol 7.71
    acetonitrile 29.57
    DMF 83.94
    toluene 1.75
    isobutanol 5.81
    1,4-dioxane 46.1
    methyl acetate 59.31
    THF 146.99
    2-butanone 66.26
    n-pentanol 8.83
    sec-butanol 10.65
    n-hexane 0.21
    ethylene glycol 16.81
    NMP 137.52
    cyclohexane 0.27
    DMSO 219.08
    n-butyl acetate 17.62
    n-octanol 8.85
    chloroform 0.92
    n-propyl acetate 22.27
    acetic acid 27.81
    dichloromethane 3.09
    cyclohexanone 24.8
    propylene glycol 12.38
    isopropyl acetate 15.23
    DMAc 142.25
    2-ethoxyethanol 48.09
    isopentanol 7.05
    n-heptane 0.67
    ethyl formate 16.18
    1,2-dichloroethane 5.55
    n-hexanol 9.19
    2-methoxyethanol 56.74
    isobutyl acetate 6.73
    tetrachloromethane 0.31
    n-pentyl acetate 13.36
    transcutol 72.14
    n-heptanol 8.75
    ethylbenzene 1.61
    MIBK 13.5
    2-propoxyethanol 40.29
    tert-butanol 16.06
    MTBE 14.95
    2-butoxyethanol 27.76
    propionic acid 18.65
    o-xylene 2.16
    formic acid 29.45
    diethyl ether 18.55
    m-xylene 1.31
    p-xylene 1.97
    chlorobenzene 1.34
    dimethyl carbonate 22.22
    n-octane 0.39
    formamide 64.35
    cyclopentanone 67.05
    2-pentanone 27.79
    anisole 15.15
    cyclopentyl methyl ether 18.95
    gamma-butyrolactone 78.22
    1-methoxy-2-propanol 35.99
    pyridine 24.2
    3-pentanone 25.0
    furfural 46.58
    n-dodecane 0.39
    diethylene glycol 40.01
    diisopropyl ether 3.46
    tert-amyl alcohol 13.95
    acetylacetone 42.54
    n-hexadecane 0.45
    acetophenone 19.75
    methyl propionate 33.1
    isopentyl acetate 12.51
    trichloroethylene 5.75
    n-nonanol 8.88
    cyclohexanol 4.9
    benzyl alcohol 10.32
    2-ethylhexanol 5.64
    isooctanol 5.78
    dipropyl ether 9.67
    1,2-dichlorobenzene 1.61
    ethyl lactate 15.67
    propylene carbonate 22.75
    n-methylformamide 41.67
    2-pentanol 6.15
    n-pentane 0.27
    1-propoxy-2-propanol 22.37
    1-methoxy-2-propyl acetate 25.72
    2-(2-methoxypropoxy) propanol 30.23
    mesitylene 0.91
    ε-caprolactone 28.63
    p-cymene 2.3
    epichlorohydrin 57.93
    1,1,1-trichloroethane 1.71
    2-aminoethanol 16.15
    morpholine-4-carbaldehyde 82.09
    sulfolane 106.4
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 44.69
    n-hexyl acetate 17.96
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 36.73
    sec-butyl acetate 11.37
    tert-butyl acetate 17.3
    decalin 0.2
    glycerin 22.02
    diglyme 63.75
    acrylic acid 21.37
    isopropyl myristate 7.92
    n-butyric acid 11.85
    acetyl acetate 16.76
    di(2-ethylhexyl) phthalate 8.36
    ethyl propionate 20.93
    nitromethane 110.99
    1,2-diethoxyethane 22.55
    benzonitrile 7.71
    trioctyl phosphate 6.8
    1-bromopropane 2.28
    gamma-valerolactone 67.68
    n-decanol 6.71
    triethyl phosphate 9.59
    4-methyl-2-pentanol 3.61
    propionitrile 13.82
    vinylene carbonate 15.46
    1,1,2-trichlorotrifluoroethane 31.33
    DMS 20.25
    cumene 1.35
    2-octanol 5.29
    2-hexanone 23.81
    octyl acetate 11.98
    limonene 3.38
    1,2-dimethoxyethane 57.59
    ethyl orthosilicate 7.36
    tributyl phosphate 6.75
    diacetone alcohol 30.95
    N,N-dimethylaniline 9.65
    acrylonitrile 21.39
    aniline 5.17
    1,3-propanediol 19.35
    bromobenzene 0.82
    dibromomethane 1.47
    1,1,2,2-tetrachloroethane 4.6
    2-methyl-cyclohexyl acetate 11.94
    tetrabutyl urea 12.92
    diisobutyl methanol 3.11
    2-phenylethanol 13.46
    styrene 1.86
    dioctyl adipate 13.03
    dimethyl sulfate 43.13
    ethyl butyrate 15.24
    methyl lactate 22.51
    butyl lactate 11.33
    diethyl carbonate 11.25
    propanediol butyl ether 19.8
    triethyl orthoformate 10.64
    p-tert-butyltoluene 2.14
    methyl 4-tert-butylbenzoate 19.8
    morpholine 45.77
    tert-butylamine 4.42
    n-dodecanol 4.66
    dimethoxymethane 53.82
    ethylene carbonate 13.13
    cyrene 39.89
    2-ethoxyethyl acetate 26.12
    2-ethylhexyl acetate 9.61
    1,2,4-trichlorobenzene 3.11
    4-methylpyridine 14.95
    dibutyl ether 7.66
    2,6-dimethyl-4-heptanol 3.11
    DEF 33.2
    dimethyl isosorbide 47.2
    tetrachloroethylene 3.05
    eugenol 20.42
    triacetin 21.85
    span 80 15.96
    1,4-butanediol 11.57
    1,1-dichloroethane 2.42
    2-methyl-1-pentanol 7.08
    methyl formate 39.77
    2-methyl-1-butanol 6.56
    n-decane 0.65
    butyronitrile 8.63
    3,7-dimethyl-1-octanol 5.7
    1-chlorooctane 2.67
    1-chlorotetradecane 1.19
    n-nonane 0.54
    undecane 0.51
    tert-butylcyclohexane 0.2
    cyclooctane 0.16
    cyclopentanol 9.93
    tetrahydropyran 19.1
    tert-amyl methyl ether 13.43
    2,5,8-trioxanonane 51.28
    1-hexene 1.13
    2-isopropoxyethanol 29.54
    2,2,2-trifluoroethanol 17.64
    methyl butyrate 23.17

    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