Chloranil

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  • Identifiers

    CAS number
    118-75-2

    Molecular formula
    C6Cl4O2

    SMILES
    C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 45.19%
    Sweet 43.85%
    Caramellic 43.7%
    Burnt 38.44%
    Sharp 17.76%
    Dry 16.77%
    Savory 16.66%
    Roasted 15.65%
    Bitter 14.93%
    Spicy 14.49%

     

    Flavor
    Bitter 59.27%
    Odorless 29.98%
    Nitrile 20.41%
    Roasted 20.3%
    Bread crust 20.26%
    Taco 19.91%
    Soybean 19.11%
    Nutty 19.0%
    Roasted peanuts 18.89%
    Rotten 18.88%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    3.71 (weak acid)

    Molecular weight
    245.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 552 °F (decomposes) (NTP, 1992)
    • 292 °C (SEALED TUBE)
    • 290 °C

    Boiling point

    • Sublimes (NTP, 1992)
    • Sublimes
    • SUBLIMES AT BOILING POINT

    Flash point

    • 138.75 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • ALMOST INSOL IN COLD PETROLEUM ETHER, COLD ALCOHOL; SPARINGLY SOL IN CHLOROFORM, CARBON DISULFIDE, CARBON TETRACHLORIDE; SOLUBLE IN ETHER. INSOLUBLE IN WATER.
    • g/100 g: in acetone 33, ether 16, dimethylformamide 5.4, solvent naphtha 5.4, benzene 1.3, methanol about 0.1, carbon tetrachloride about 0.1, dibutyl phthalate about 0.1
    • ALMOST INSOL IN WATER (1:4000)
    • In water, 250 mg/l at room temperature
    • Solubility in water: none

  • Synonyms

    • Chloranil
    • 118-75-2
    • p-Chloranil
    • Tetrachloro-p-benzoquinone
    • Tetrachloro-1,4-benzoquinone
    • Spergon
    • 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione
    • Tetrachlorobenzoquinone
    • Vulklor
    • Coversan
    • Reranil
    • Tetrachloroquinone
    • Khloranil
    • Psorisan
    • 2,3,5,6-TETRACHLORO-1,4-BENZOQUINONE
    • Spergon technical
    • Spergon I
    • Tetrachloro-p-quinone
    • Chloranile
    • Quinone tetrachloride
    • Tetrachloroparabenzoquinone
    • Geigy-444E
    • 2,3,5,6-Tetrachloro-p-benzoquinone
    • Dow Seed Disinfectant No. 5
    • 2,3,5,6-Tetrachlorobenzo-1,4-quinone
    • 2,3,5,6-Tetrachloro-2,5-cyclohexadiene-1,4-dione
    • 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro-
    • Caswell No. 171
    • 2,3,5,6-Tetrachloroquinone
    • ENT 3,797
    • G-444E
    • 2,3,5,6-Tetrachlorobenzoquinone
    • p-Benzoquinone, 2,3,5,6-tetrachloro-
    • NSC 8432
    • CCRIS 7155
    • alpha-Chloranil
    • HSDB 1533
    • Tetrachlorquinone
    • G-25804
    • 1,4-Benzoquinone, 2,3,5,6-tetrachloro-
    • EINECS 204-274-4
    • .alpha.-Chloranil
    • EPA Pesticide Chemical Code 079301
    • 01W5X7N5XV
    • DTXSID2020266
    • CHEBI:36703
    • AI3-03797
    • CHLORANIL [MI]
    • NSC-8432
    • CHLORANIL [HSDB]
    • MFCD00001594
    • CHLORANIL [WHO-DD]
    • 2,3,5,6-Tetrachlor-1,4-benzochinon
    • DTXCID20266
    • tetrachlorocyclohexa-2,5-diene-1,4-dione
    • EC 204-274-4
    • ENT 3797
    • 2,3,5,6-tetrachloro-[1,4]benzoquinone
    • TCBQ compound
    • 4-Chloranil
    • CAS-118-75-2
    • pchloranil
    • UNII-01W5X7N5XV
    • Tetrachloro 1,4 benzoquinone
    • para-chloranil
    • tetrachloro-1
    • Tetrachloropquinone
    • Geigy444E
    • P-CHLORONIL
    • Tetrachloropbenzoquinone
    • ACTOR CL
    • Spectrum_001590
    • SpecPlus_000850
    • Spectrum2_000024
    • Spectrum3_001660
    • Spectrum4_000794
    • Spectrum5_001386
    • Tetrachloro1,4benzoquinone
    • 2,5,6-Tetrachloroquinone
    • 2,3,5,6Tetrachloroquinone
    • Dow Seed Disinfectant No 5
    • SCHEMBL24049
    • BSPBio_003419
    • KBioGR_001268
    • KBioSS_002070
    • DivK1c_006946
    • SPECTRUM1504212
    • SPBio_000087
    • 2,5,6-Tetrachlorobenzoquinone
    • CHEMBL192627
    • 2,3,5,6Tetrachlorobenzoquinone
    • BDBM22782
    • KBio1_001890
    • KBio2_002070
    • KBio2_004638
    • KBio2_007206
    • KBio3_002639
    • 2,3,5,6Tetrachloropbenzoquinone
    • NSC8432
    • 2,5,6-Tetrachloro-p-benzoquinone
    • G444E
    • HY-Y0278
    • WLN: L6V DVJ BG CG EG FG
    • p-Benzoquinone,3,5,6-tetrachloro-
    • pBenzoquinone, 2,3,5,6tetrachloro
    • Tox21_201656
    • Tox21_303021
    • 2,3,5,6Tetrachloro1,4benzoquinone
    • CCG-39987
    • STK396683
    • Tetrachloro-1,4-benzoquinone, 99%
    • 2,5,6-Tetrachloro-1,4-benzoquinone
    • AKOS001569085
    • Chloranil, purum, >=97.0% (AT)
    • 2,4-dione, 2,3,5,6-tetrachloro-
    • FT33950
    • 1,4Benzoquinone, 2,3,5,6tetrachloro
    • 1,2,4,5-TETRACHLOROBENZOQUINONE
    • NCGC00091254-01
    • NCGC00091254-02
    • NCGC00091254-03
    • NCGC00091254-04
    • NCGC00091254-05
    • NCGC00256410-01
    • NCGC00259205-01
    • AC-11776
    • AS-14117
    • BP-30129

  • Applications

    Chloranil is mainly used as an oxidizing agent in organic synthesis, for example in oxidations of hydroquinones and other electron-rich substrates to give quinones. It also serves as an important intermediate in the production of dyes and pigments, enabling synthesis of colored quinone systems used in textile, paint, and paper industries. In the area of organic electronics and semiconductors, chloranil acts as an electron acceptor to form charge-transfer complexes and to dope conjugated polymers for advanced electronic materials. Additionally, it may be used as an oxidizing reagent in analytical chemistry and laboratory research, and is regarded as a colorant precursor for coating and printing formulations, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.67
    methanol 1.59
    isopropanol 1.46
    water 0.19
    ethyl acetate 12.2
    n-propanol 1.7
    acetone 12.19
    n-butanol 1.4
    acetonitrile 7.72
    DMF 29.5
    toluene 10.11
    isobutanol 1.5
    1,4-dioxane 25.2
    methyl acetate 15.17
    THF 38.46
    2-butanone 13.04
    n-pentanol 1.97
    sec-butanol 2.23
    n-hexane 1.92
    ethylene glycol 1.07
    NMP 63.31
    cyclohexane 3.76
    DMSO 27.74
    n-butyl acetate 11.77
    n-octanol 3.62
    chloroform 16.54
    n-propyl acetate 9.5
    acetic acid 3.47
    dichloromethane 21.42
    cyclohexanone 19.13
    propylene glycol 0.69
    isopropyl acetate 11.55
    DMAc 56.03
    2-ethoxyethanol 7.29
    isopentanol 1.77
    n-heptane 3.45
    ethyl formate 6.18
    1,2-dichloroethane 14.73
    n-hexanol 2.86
    2-methoxyethanol 7.5
    isobutyl acetate 5.84
    tetrachloromethane 5.72
    n-pentyl acetate 9.18
    transcutol 21.56
    n-heptanol 2.92
    ethylbenzene 10.65
    MIBK 8.69
    2-propoxyethanol 9.42
    tert-butanol 2.73
    MTBE 9.37
    2-butoxyethanol 6.97
    propionic acid 3.03
    o-xylene 14.35
    formic acid 2.44
    diethyl ether 10.57
    m-xylene 9.03
    p-xylene 12.91
    chlorobenzene 8.01
    dimethyl carbonate 11.34
    n-octane 2.1
    formamide 8.48
    cyclopentanone 29.5
    2-pentanone 9.65
    anisole 22.03
    cyclopentyl methyl ether 22.51
    gamma-butyrolactone 33.47
    1-methoxy-2-propanol 5.97
    pyridine 20.25
    3-pentanone 14.7
    furfural 31.45
    n-dodecane 1.53
    diethylene glycol 6.22
    diisopropyl ether 7.97
    tert-amyl alcohol 4.07
    acetylacetone 23.19
    n-hexadecane 1.83
    acetophenone 23.26
    methyl propionate 12.71
    isopentyl acetate 10.93
    trichloroethylene 26.99
    n-nonanol 4.03
    cyclohexanol 3.95
    benzyl alcohol 7.48
    2-ethylhexanol 4.39
    isooctanol 2.94
    dipropyl ether 11.58
    1,2-dichlorobenzene 11.53
    ethyl lactate 5.01
    propylene carbonate 16.46
    n-methylformamide 8.75
    2-pentanol 1.95
    n-pentane 1.37
    1-propoxy-2-propanol 8.01
    1-methoxy-2-propyl acetate 18.71
    2-(2-methoxypropoxy) propanol 13.14
    mesitylene 8.18
    ε-caprolactone 19.58
    p-cymene 10.26
    epichlorohydrin 30.43
    1,1,1-trichloroethane 13.69
    2-aminoethanol 1.58
    morpholine-4-carbaldehyde 44.6
    sulfolane 44.12
    2,2,4-trimethylpentane 1.69
    2-methyltetrahydrofuran 26.71
    n-hexyl acetate 9.94
    isooctane 1.07
    2-(2-butoxyethoxy)ethanol 10.93
    sec-butyl acetate 9.78
    tert-butyl acetate 15.74
    decalin 3.65
    glycerin 1.65
    diglyme 29.82
    acrylic acid 3.71
    isopropyl myristate 7.43
    n-butyric acid 2.86
    acetyl acetate 13.95
    di(2-ethylhexyl) phthalate 5.9
    ethyl propionate 12.2
    nitromethane 17.56
    1,2-diethoxyethane 17.5
    benzonitrile 10.3
    trioctyl phosphate 4.14
    1-bromopropane 7.79
    gamma-valerolactone 34.11
    n-decanol 3.32
    triethyl phosphate 11.76
    4-methyl-2-pentanol 2.11
    propionitrile 4.9
    vinylene carbonate 12.43
    1,1,2-trichlorotrifluoroethane 19.22
    DMS 17.26
    cumene 7.93
    2-octanol 2.86
    2-hexanone 10.19
    octyl acetate 7.46
    limonene 12.23
    1,2-dimethoxyethane 25.08
    ethyl orthosilicate 11.35
    tributyl phosphate 5.6
    diacetone alcohol 10.59
    N,N-dimethylaniline 21.29
    acrylonitrile 7.07
    aniline 7.83
    1,3-propanediol 1.83
    bromobenzene 10.02
    dibromomethane 14.16
    1,1,2,2-tetrachloroethane 21.01
    2-methyl-cyclohexyl acetate 13.98
    tetrabutyl urea 10.27
    diisobutyl methanol 4.6
    2-phenylethanol 8.96
    styrene 10.57
    dioctyl adipate 9.66
    dimethyl sulfate 27.92
    ethyl butyrate 13.55
    methyl lactate 5.99
    butyl lactate 5.69
    diethyl carbonate 10.63
    propanediol butyl ether 4.18
    triethyl orthoformate 12.74
    p-tert-butyltoluene 9.51
    methyl 4-tert-butylbenzoate 16.79
    morpholine 19.95
    tert-butylamine 2.53
    n-dodecanol 2.86
    dimethoxymethane 19.65
    ethylene carbonate 10.16
    cyrene 17.59
    2-ethoxyethyl acetate 14.66
    2-ethylhexyl acetate 11.77
    1,2,4-trichlorobenzene 15.89
    4-methylpyridine 18.87
    dibutyl ether 8.92
    2,6-dimethyl-4-heptanol 4.6
    DEF 22.82
    dimethyl isosorbide 37.85
    tetrachloroethylene 17.44
    eugenol 13.42
    triacetin 16.65
    span 80 7.54
    1,4-butanediol 1.29
    1,1-dichloroethane 8.31
    2-methyl-1-pentanol 2.62
    methyl formate 9.0
    2-methyl-1-butanol 1.94
    n-decane 2.49
    butyronitrile 3.9
    3,7-dimethyl-1-octanol 4.22
    1-chlorooctane 5.17
    1-chlorotetradecane 2.98
    n-nonane 2.34
    undecane 1.9
    tert-butylcyclohexane 2.79
    cyclooctane 3.08
    cyclopentanol 5.31
    tetrahydropyran 14.35
    tert-amyl methyl ether 12.19
    2,5,8-trioxanonane 25.04
    1-hexene 3.53
    2-isopropoxyethanol 6.79
    2,2,2-trifluoroethanol 5.14
    methyl butyrate 12.2

    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