(1E,2E)-1,2-Cyclohexanedione 1,2-dioxime

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  • Identifiers

    CAS number
    73322-77-7

    Molecular formula
    C6H10N2O2

    SMILES
    C1C/C(=N\O)/C(=N/O)/CC1

    Safety labels

  • Odor profile

    Fragrance
    Roasted 33.38%
    Nutty 29.58%
    Meaty 26.27%
    Green 26.08%
    Odorless 24.59%
    Popcorn 23.6%
    Pungent 22.54%
    Cooked 20.73%
    Fishy 20.0%
    Savory 18.89%

     

    Flavor
    Bitter 32.92%
    Roasted 31.24%
    Nutty 25.62%
    Roast 24.53%
    Odorless 23.13%
    Taco 22.68%
    Cooked 22.19%
    Shrimp 21.51%
    Bread crust 21.07%
    Roasted peanuts 20.76%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    9.3 (weak base)

    Molecular weight
    142.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    333°C

    Flash point

    • 139.28 ˚C est.

  • Synonyms

    • 73322-77-7
    • (1E,2E)-1,2-Cyclohexanedione 1,2-dioxime
    • RefChem:204832
    • 492-99-9
    • NIOXIME
    • 1,2-Cyclohexanedione dioxime
    • (1Z,2Z)-Cyclohexane-1,2-dione dioxime
    • MFCD00001663
    • N-(2-nitrosocyclohexen-1-yl)hydroxylamine
    • Nioxim
    • 1,2-Bis(hydroxyimino)cyclohexane
    • NSC-4076
    • (1E,2E)-cyclohexane-1,2-dione dioxime
    • CYCLOHEXANE-1,2-DIONE DIOXIME
    • cyclohexanedione dioxime
    • G1QT7SU5A8
    • cyclohexane-1,2-dione oxime
    • 1,2-di(hydroxyimino)cyclohexane
    • N,N'-Cyclohexane-1,2-diylidenedihydroxylamine
    • starbld0000630
    • NIOXIME [II]
    • NIOXIME [MI]
    • (NE)-N-[(2E)-2-hydroxyiminocyclohexylidene]hydroxylamine
    • NSC4076
    • CUNNCKOPAWXYDX-KQQUZDAGSA-N
    • DTXSID301275718
    • 1,2-Cyclohexanedione dioxime, 96%
    • STK448066
    • STL593309
    • AKOS003726087
    • SY057062
    • n-hydroxy-2-nitrosocyclohex-1-en-1-amine
    • ST50823780
    • (1E,2E)-N,N'-dihydroxycyclohexane-1,2-diimine
    • 1,2-CYCLOHEXANEDIONE, 1,2-DIOXIME, (1E,2E)-
    • 492-99-9

  • Applications

    (1E,2E)-1,2-Cyclohexanedione 1,2-dioxime (CAS 73322-77-7) is used as a bidentate chelating ligand for metal ions in analytical chemistry and catalysis, often forming metal chelate complexes that serve as reagents or catalysts in various processes. It also functions as an intermediate in organic synthesis for the construction of coordination compounds and heterocycles. In industry, it is used as a coordinating additive in coatings, inks, and cleaning formulations to sequester metal ions, and it may be employed in polymer processing or metal-catalyzed polymerization as a ligand or stabilizer.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 28.28
    methanol 42.92
    isopropanol 19.74
    water 1.21
    ethyl acetate 13.85
    n-propanol 21.56
    acetone 32.54
    n-butanol 16.76
    acetonitrile 18.17
    DMF 111.43
    toluene 3.16
    isobutanol 14.46
    1,4-dioxane 44.75
    methyl acetate 19.52
    THF 69.72
    2-butanone 26.4
    n-pentanol 14.58
    sec-butanol 15.28
    n-hexane 0.77
    ethylene glycol 19.54
    NMP 118.29
    cyclohexane 0.77
    DMSO 239.91
    n-butyl acetate 18.23
    n-octanol 12.95
    chloroform 74.28
    n-propyl acetate 10.82
    acetic acid 39.75
    dichloromethane 71.63
    cyclohexanone 52.43
    propylene glycol 17.02
    isopropyl acetate 10.11
    DMAc 83.01
    2-ethoxyethanol 37.47
    isopentanol 15.02
    n-heptane 0.95
    ethyl formate 21.5
    1,2-dichloroethane 51.32
    n-hexanol 18.61
    2-methoxyethanol 64.7
    isobutyl acetate 7.07
    tetrachloromethane 9.62
    n-pentyl acetate 16.7
    transcutol 88.83
    n-heptanol 13.36
    ethylbenzene 4.51
    MIBK 14.03
    2-propoxyethanol 44.49
    tert-butanol 20.54
    MTBE 9.14
    2-butoxyethanol 32.74
    propionic acid 27.22
    o-xylene 6.24
    formic acid 33.54
    diethyl ether 6.94
    m-xylene 5.19
    p-xylene 7.07
    chlorobenzene 18.34
    dimethyl carbonate 10.58
    n-octane 0.87
    formamide 45.57
    cyclopentanone 80.22
    2-pentanone 18.28
    anisole 13.01
    cyclopentyl methyl ether 16.73
    gamma-butyrolactone 104.17
    1-methoxy-2-propanol 44.82
    pyridine 34.0
    3-pentanone 14.22
    furfural 95.21
    n-dodecane 0.94
    diethylene glycol 52.62
    diisopropyl ether 2.95
    tert-amyl alcohol 16.32
    acetylacetone 29.21
    n-hexadecane 1.07
    acetophenone 20.74
    methyl propionate 16.48
    isopentyl acetate 17.4
    trichloroethylene 108.13
    n-nonanol 11.99
    cyclohexanol 14.81
    benzyl alcohol 17.95
    2-ethylhexanol 11.99
    isooctanol 11.25
    dipropyl ether 7.39
    1,2-dichlorobenzene 26.14
    ethyl lactate 15.91
    propylene carbonate 45.66
    n-methylformamide 55.61
    2-pentanol 10.47
    n-pentane 0.51
    1-propoxy-2-propanol 29.48
    1-methoxy-2-propyl acetate 23.33
    2-(2-methoxypropoxy) propanol 30.02
    mesitylene 4.94
    ε-caprolactone 44.65
    p-cymene 6.92
    epichlorohydrin 89.48
    1,1,1-trichloroethane 32.04
    2-aminoethanol 26.49
    morpholine-4-carbaldehyde 87.71
    sulfolane 186.79
    2,2,4-trimethylpentane 0.83
    2-methyltetrahydrofuran 32.29
    n-hexyl acetate 22.0
    isooctane 0.79
    2-(2-butoxyethoxy)ethanol 39.2
    sec-butyl acetate 7.3
    tert-butyl acetate 13.98
    decalin 1.45
    glycerin 36.48
    diglyme 64.81
    acrylic acid 32.12
    isopropyl myristate 9.0
    n-butyric acid 28.51
    acetyl acetate 12.25
    di(2-ethylhexyl) phthalate 13.72
    ethyl propionate 10.77
    nitromethane 75.96
    1,2-diethoxyethane 20.23
    benzonitrile 25.4
    trioctyl phosphate 11.07
    1-bromopropane 13.99
    gamma-valerolactone 97.65
    n-decanol 9.19
    triethyl phosphate 11.84
    4-methyl-2-pentanol 8.03
    propionitrile 16.21
    vinylene carbonate 43.78
    1,1,2-trichlorotrifluoroethane 78.97
    DMS 22.48
    cumene 5.42
    2-octanol 9.89
    2-hexanone 13.75
    octyl acetate 12.53
    limonene 8.55
    1,2-dimethoxyethane 46.88
    ethyl orthosilicate 10.3
    tributyl phosphate 12.3
    diacetone alcohol 28.98
    N,N-dimethylaniline 12.84
    acrylonitrile 31.07
    aniline 11.96
    1,3-propanediol 34.7
    bromobenzene 15.78
    dibromomethane 39.35
    1,1,2,2-tetrachloroethane 87.63
    2-methyl-cyclohexyl acetate 15.65
    tetrabutyl urea 18.32
    diisobutyl methanol 8.07
    2-phenylethanol 21.5
    styrene 5.03
    dioctyl adipate 14.35
    dimethyl sulfate 36.31
    ethyl butyrate 12.8
    methyl lactate 23.96
    butyl lactate 20.31
    diethyl carbonate 10.23
    propanediol butyl ether 33.08
    triethyl orthoformate 11.35
    p-tert-butyltoluene 6.8
    methyl 4-tert-butylbenzoate 27.47
    morpholine 49.2
    tert-butylamine 9.78
    n-dodecanol 7.07
    dimethoxymethane 33.95
    ethylene carbonate 30.39
    cyrene 36.71
    2-ethoxyethyl acetate 22.53
    2-ethylhexyl acetate 13.44
    1,2,4-trichlorobenzene 32.58
    4-methylpyridine 24.94
    dibutyl ether 8.94
    2,6-dimethyl-4-heptanol 8.07
    DEF 29.47
    dimethyl isosorbide 51.13
    tetrachloroethylene 55.03
    eugenol 29.3
    triacetin 23.62
    span 80 25.04
    1,4-butanediol 18.62
    1,1-dichloroethane 32.17
    2-methyl-1-pentanol 12.88
    methyl formate 44.21
    2-methyl-1-butanol 13.58
    n-decane 1.45
    butyronitrile 16.37
    3,7-dimethyl-1-octanol 12.07
    1-chlorooctane 7.59
    1-chlorotetradecane 3.14
    n-nonane 1.22
    undecane 1.15
    tert-butylcyclohexane 1.51
    cyclooctane 0.45
    cyclopentanol 26.97
    tetrahydropyran 20.54
    tert-amyl methyl ether 9.05
    2,5,8-trioxanonane 46.74
    1-hexene 3.05
    2-isopropoxyethanol 22.36
    2,2,2-trifluoroethanol 26.32
    methyl butyrate 17.38

    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