2,6-Dimethoxy-1,4-Benzoquinone

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  • Identifiers

    CAS number
    530-55-2

    Molecular formula
    C8H8O4

    SMILES
    COC1=CC(=O)C=C(C1=O)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 81.84%
    Sweet 69.24%
    Burnt 55.8%
    Fruity 46.47%
    Nutty 38.24%
    Roasted 38.0%
    Buttery 37.19%
    Coffee 31.97%
    Rummy 27.01%
    Ethereal 24.89%

     

    Flavor
    Caramel 49.87%
    Maple 35.28%
    Fruity 34.24%
    Sugar 30.47%
    Buttery 24.9%
    Cotton candy 23.39%
    Extremely sweet 23.18%
    Seedy 22.94%
    Sweet 22.32%
    Fenugreek 22.2%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    5.7 (weak acid)

    Molecular weight
    168.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    298°C

    Melting point expt.

    • 252 °C

    Flash point

    • 99.56 ˚C est.

  • Synonyms

    • 2,6-Dimethoxy-1,4-benzoquinone
    • 530-55-2
    • 2,6-Dimethoxyquinone
    • 2,6-Dimethoxy-p-benzoquinone
    • 2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
    • 2,6-Dimethoxy-p-quinone
    • 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-
    • p-Benzoquinone, 2,6-dimethoxy-
    • DTXSID80862128
    • NSC-24500
    • NSC-56336
    • 1Z701W789S
    • RefChem:25890
    • DTXCID30810937
    • 208-484-7
    • 2,6-Dimethoxybenzoquinone
    • MFCD00016368
    • 2,6-Dimethoxysemiquinone anions
    • 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione
    • NSC 24500
    • 2,6-Dimethoxybenzo-1,4-quinone
    • 2,6-Dimethoxysemiquinone radicals
    • NSC24500
    • ghl.PD_Mitscher_leg0.4
    • MLS002207260
    • NSC 56336
    • 26547-64-8
    • SMR001306787
    • p-Benzoquinone,6-dimethoxy-
    • 2,4-dione, 2,6-dimethoxy-
    • DIMETHOXYBENZOQUINONE,6-
    • 3,5-Dimethoxy-1,4-benzoquinone; 3,5-Dimethoxybenzoquinone; NSC 24500
    • EINECS 208-484-7
    • UNII-1Z701W789S
    • Spectrum_000723
    • 2, 6-Dimethoxyquinone
    • Maybridge1_002628
    • Spectrum2_000781
    • Spectrum3_000177
    • Spectrum4_001608
    • Spectrum5_000335
    • Quinone, 2,6-dimethoxy-
    • 2,6-Dimetoxy-p-benzoquinone
    • 2-6-DIMETHOXYQUINONE
    • BSPBio_001673
    • KBioGR_001955
    • KBioSS_001203
    • SPECTRUM200413
    • cid_68262
    • DivK1c_001380
    • SCHEMBL570683
    • SPBio_000882
    • 2, 6-Dimethoxy-p-benzoquinone
    • CHEMBL448515
    • orb1303820
    • BDBM80763
    • HMS548P10
    • KBio2_001203
    • KBio2_003771
    • KBio2_006339
    • KBio3_001173
    • OLBNOBQOQZRLMP-UHFFFAOYSA-
    • 2,6-dimethoxy[1,4]benzoquinone
    • 3,5-Dimethoxy-1,4-benzoquinone
    • HMS1922P16
    • 2, 6-Dimethoxy-1,4-benzoquinone
    • 2,6-dimethoxy-[1,4]benzoquinone
    • DIMETHOXYBENZOQUINONE,2,6-
    • 2,6-DIMETHOXYQUINONE [MI]
    • HY-N1677
    • NSC56336
    • CCG-40159
    • SBB057170
    • AKOS015851594
    • EBC-616542
    • FD42586
    • FS-4243
    • SDCCGMLS-0066389.P001
    • CDS1_000340
    • 2,6-Dimethoxy-1,4-benzoquinone, 97%
    • NCGC00095215-01
    • NCGC00095215-02
    • NCGC00095215-03
    • NCGC00095215-04
    • NCGC00095215-05
    • NCI60_001958
    • PD002219
    • SY048603
    • DB-020224
    • CS-0017339
    • D2706
    • NS00006663
    • ST50331798
    • D90101
    • F239598
    • SR-05000002399
    • Q4596807
    • SR-05000002399-1
    • 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy- (9CI)
    • 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-, radical ion(1-)
    • InChI=1/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3
    • KIA
    • 530-55-2

  • Applications

    2,6-Dimethoxy-1,4-Benzoquinone is primarily used as an organic-synthesis intermediate and as a redox-active reagent in specialty chemical manufacturing; it serves as a building block for the synthesis of quinone-based dyes, pigments, and related intermediates; it can function as a redox facilitator in various oxidation–reduction steps within process chemistry; it is explored as a precursor for quinone-containing polymers and specialty plastics, enabling the introduction of redox-active motifs into materials; in pharmaceutical and agrochemical development, it is commonly evaluated as a synthetic building block for routes to active ingredients and intermediates; and it is studied as a redox mediator in electronics and energy-storage research, where its reversible redox chemistry can be leveraged in conducting systems and organic batteries.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.81
    methanol 12.47
    isopropanol 4.11
    water 0.96
    ethyl acetate 16.22
    n-propanol 4.59
    acetone 24.23
    n-butanol 3.99
    acetonitrile 20.07
    DMF 92.82
    toluene 7.35
    isobutanol 3.51
    1,4-dioxane 39.41
    methyl acetate 27.43
    THF 38.86
    2-butanone 15.11
    n-pentanol 3.8
    sec-butanol 3.07
    n-hexane 0.56
    ethylene glycol 14.24
    NMP 93.02
    cyclohexane 2.05
    DMSO 97.25
    n-butyl acetate 10.85
    n-octanol 5.39
    chloroform 50.37
    n-propyl acetate 9.7
    acetic acid 9.55
    dichloromethane 66.69
    cyclohexanone 32.48
    propylene glycol 4.51
    isopropyl acetate 7.57
    DMAc 81.9
    2-ethoxyethanol 17.35
    isopentanol 3.93
    n-heptane 1.04
    ethyl formate 29.63
    1,2-dichloroethane 40.37
    n-hexanol 6.18
    2-methoxyethanol 39.98
    isobutyl acetate 5.98
    tetrachloromethane 11.48
    n-pentyl acetate 7.09
    transcutol 18.63
    n-heptanol 4.49
    ethylbenzene 6.65
    MIBK 7.06
    2-propoxyethanol 21.52
    tert-butanol 6.2
    MTBE 3.97
    2-butoxyethanol 11.77
    propionic acid 10.37
    o-xylene 9.8
    formic acid 17.82
    diethyl ether 5.29
    m-xylene 6.39
    p-xylene 9.93
    chlorobenzene 18.55
    dimethyl carbonate 19.96
    n-octane 0.73
    formamide 34.25
    cyclopentanone 40.52
    2-pentanone 10.62
    anisole 15.8
    cyclopentyl methyl ether 13.03
    gamma-butyrolactone 62.82
    1-methoxy-2-propanol 17.82
    pyridine 35.31
    3-pentanone 11.24
    furfural 89.45
    n-dodecane 0.93
    diethylene glycol 37.4
    diisopropyl ether 1.8
    tert-amyl alcohol 4.57
    acetylacetone 23.85
    n-hexadecane 1.1
    acetophenone 21.85
    methyl propionate 20.09
    isopentyl acetate 9.16
    trichloroethylene 68.52
    n-nonanol 5.34
    cyclohexanol 7.69
    benzyl alcohol 17.1
    2-ethylhexanol 5.85
    isooctanol 3.93
    dipropyl ether 4.81
    1,2-dichlorobenzene 26.45
    ethyl lactate 12.27
    propylene carbonate 36.07
    n-methylformamide 44.71
    2-pentanol 2.37
    n-pentane 0.46
    1-propoxy-2-propanol 11.45
    1-methoxy-2-propyl acetate 16.92
    2-(2-methoxypropoxy) propanol 15.01
    mesitylene 5.22
    ε-caprolactone 31.32
    p-cymene 6.58
    epichlorohydrin 57.06
    1,1,1-trichloroethane 25.63
    2-aminoethanol 9.6
    morpholine-4-carbaldehyde 79.2
    sulfolane 86.83
    2,2,4-trimethylpentane 0.5
    2-methyltetrahydrofuran 17.78
    n-hexyl acetate 9.55
    isooctane 0.36
    2-(2-butoxyethoxy)ethanol 15.46
    sec-butyl acetate 5.45
    tert-butyl acetate 8.05
    decalin 2.1
    glycerin 16.0
    diglyme 35.48
    acrylic acid 15.12
    isopropyl myristate 5.42
    n-butyric acid 10.82
    acetyl acetate 14.7
    di(2-ethylhexyl) phthalate 8.57
    ethyl propionate 11.19
    nitromethane 47.25
    1,2-diethoxyethane 8.23
    benzonitrile 24.25
    trioctyl phosphate 6.43
    1-bromopropane 9.25
    gamma-valerolactone 59.6
    n-decanol 4.5
    triethyl phosphate 13.97
    4-methyl-2-pentanol 2.3
    propionitrile 13.55
    vinylene carbonate 42.16
    1,1,2-trichlorotrifluoroethane 60.16
    DMS 18.81
    cumene 5.98
    2-octanol 3.16
    2-hexanone 8.51
    octyl acetate 6.96
    limonene 7.72
    1,2-dimethoxyethane 42.3
    ethyl orthosilicate 10.9
    tributyl phosphate 7.34
    diacetone alcohol 13.82
    N,N-dimethylaniline 16.1
    acrylonitrile 26.92
    aniline 13.09
    1,3-propanediol 12.65
    bromobenzene 19.11
    dibromomethane 33.86
    1,1,2,2-tetrachloroethane 54.02
    2-methyl-cyclohexyl acetate 12.51
    tetrabutyl urea 13.33
    diisobutyl methanol 4.14
    2-phenylethanol 17.22
    styrene 7.63
    dioctyl adipate 10.28
    dimethyl sulfate 47.46
    ethyl butyrate 11.03
    methyl lactate 19.36
    butyl lactate 7.9
    diethyl carbonate 12.62
    propanediol butyl ether 8.69
    triethyl orthoformate 10.02
    p-tert-butyltoluene 5.77
    methyl 4-tert-butylbenzoate 18.89
    morpholine 31.0
    tert-butylamine 3.52
    n-dodecanol 3.88
    dimethoxymethane 40.65
    ethylene carbonate 32.22
    cyrene 27.99
    2-ethoxyethyl acetate 11.45
    2-ethylhexyl acetate 8.55
    1,2,4-trichlorobenzene 30.49
    4-methylpyridine 30.28
    dibutyl ether 4.81
    2,6-dimethyl-4-heptanol 4.14
    DEF 27.61
    dimethyl isosorbide 33.28
    tetrachloroethylene 46.59
    eugenol 20.21
    triacetin 13.77
    span 80 10.02
    1,4-butanediol 7.07
    1,1-dichloroethane 18.94
    2-methyl-1-pentanol 3.92
    methyl formate 54.0
    2-methyl-1-butanol 3.44
    n-decane 1.23
    butyronitrile 11.24
    3,7-dimethyl-1-octanol 5.52
    1-chlorooctane 4.99
    1-chlorotetradecane 2.85
    n-nonane 1.05
    undecane 1.07
    tert-butylcyclohexane 1.34
    cyclooctane 0.9
    cyclopentanol 10.16
    tetrahydropyran 14.09
    tert-amyl methyl ether 4.43
    2,5,8-trioxanonane 29.51
    1-hexene 1.88
    2-isopropoxyethanol 10.14
    2,2,2-trifluoroethanol 17.05
    methyl butyrate 17.24

    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