2,2'-(Dithiodimethylene)difuran

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  • Identifiers

    CAS number
    4437-20-1

    Molecular formula
    C10H10O2S2

    SMILES
    C1=COC(=C1)CSSCC2=CC=CO2

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sulfurous 84.61%
    Roasted 76.06%
    Meaty 74.44%
    Coffee 72.45%
    Savory 55.5%
    Onion 55.04%
    Alliaceous 52.95%
    Garlic 52.1%
    Burnt 50.89%
    Cooked 45.95%

     

    Flavor
    Sulfury 77.26%
    Meaty 73.44%
    Coffee 72.43%
    Roasted 71.4%
    Onion 61.76%
    Cabbage 41.24%
    Burnt 39.84%
    Chicken 39.14%
    Cooked 39.01%
    Mushroom 38.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    4.21 (weak acid)

    Molecular weight
    226.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 10 - 11 °C

    Boiling point

    • 229.00 to 230.00 °C. @ 760.00 mm Hg

    Flash point

    • 141.49 ˚C est.

    Solubility expt.

    • Slightly soluble in water; soluble in oils
    • Miscible at room temperature (in ethanol)

  • Synonyms

    • DIFURFURYL DISULFIDE
    • 4437-20-1
    • Difurfuryldisulfide
    • Furfuryl disulfide
    • 1,2-Bis(furan-2-ylmethyl)disulfane
    • Furan, 2,2'-[dithiobis(methylene)]bis-
    • 2,2'-(Dithiodimethylene)difuran
    • 2-Furfuryl disulfide
    • coffee difuran
    • Bis(2-furfuryl)disulfide
    • Bis(2-furfuryl) disulfide
    • bis(2-furanylmethyl) disulfide
    • FEMA No. 3146
    • 2,2'-(thiodimethylene)-difuran
    • 2-[(furan-2-ylmethyldisulfanyl)methyl]furan
    • 2,2'-(Dithiobis(methylene))bisfuran
    • 2,2'-[Dithiobis(methylene)]bisfuran
    • 5IP6729ULF
    • bis-Furfuryl disulfide
    • di-2-Furfuryl disulfide
    • DIFURFURYL DISUFIDE
    • EINECS 224-649-6
    • Furan, 2,2'-(dithiodimethylene)di-
    • bis(2-Furylmethyl)disulfide
    • bis-(Furylmethyl) disulfide
    • bis(2-furylmethyl) disulphide
    • Furan, 2,2'-(dithiobis(methylene))bis-
    • MLS001359844
    • DTXSID3063463
    • SMR001224400
    • 2-{[(furan-2-ylmethyl)disulfanyl]methyl}furan
    • 2,2'-(THIODIMETHYLENE)-DIFURAN [FHFI]
    • 2,2'-(Dithiobis(methylene))bis-Furan
    • 2,2'-[Dithiobis(methylene)]bis-Furan
    • UNII-5IP6729ULF
    • Difurfuryldisulfid
    • 2,2'-(dithiodimethylene)-difuran
    • difurfuryl-disulfide
    • MFCD00010082
    • 2-Difurfuryl disulfide
    • Bis-2-furfuryldisulphide
    • Furfuryl disulfide, 95%
    • Bis-2-Furfuryl disulphide
    • SCHEMBL891217
    • CHEMBL1331840
    • DTXCID2040315
    • FEMA 3146
    • 2,2 inverted exclamation marka-(Dithiodimethylene)difuran
    • CHEBI:171681
    • HMS3058N08
    • 2,2'-(Dithiodimethylene)di-Furan
    • AKOS015900548
    • CS-W013023
    • SB60952
    • NCGC00247288-01
    • 2-[(uran-2-ylmethyldisulanyl)methyl]uran
    • AS-61704
    • 2,2'-[Dithiobis(methylene)]bisfuran, 9CI
    • 2-([(2-Furylmethyl)disulfanyl]methyl)furan
    • D1384
    • NS00022195
    • 2,2'-(Dithiodimethylene)difuran, >=95%, FG
    • 2-([(2-Furylmethyl)disulfanyl]methyl)furan #
    • D89846
    • 2-({[(furan-2-yl)methyl]disulfanyl}methyl)furan
    • SR-01000854182
    • 2,2-Dithiobis(methylene)bisfuran; Furfuryldisulfide
    • SR-01000854182-2
    • Q27262341
    • InChI=1/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H

  • Applications

    2,2′-(Dithiodimethylene)difuran (CAS 4437-20-1) is a sulfur-rich, disulfide-bridged heteroaromatic molecule used as a reversible cross-linker and degradable spacer in conductive polymers, a synthetic intermediate for furan-sulfur pharmaceuticals, a cleavable crosslink in hydrogels, an antioxidant and redox stabilizer for extending rubber lifetime, an electron-modulating additive in organic energy-storage batteries via S–S redox shuttling, and a versatile green-chemistry building block for UV-responsive disulfide incorporation in bio-adhesives, recyclable 3-D printing resins, and self-healing surfaces.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 50.11
    methanol 52.96
    isopropanol 36.67
    water 0.12
    ethyl acetate 169.02
    n-propanol 46.44
    acetone 233.71
    n-butanol 36.62
    acetonitrile 198.13
    DMF 353.98
    toluene 193.71
    isobutanol 37.81
    1,4-dioxane 668.89
    methyl acetate 233.88
    THF 562.2
    2-butanone 230.96
    n-pentanol 47.17
    sec-butanol 49.63
    n-hexane 7.31
    ethylene glycol 36.6
    NMP 244.73
    cyclohexane 32.23
    DMSO 642.5
    n-butyl acetate 95.9
    n-octanol 53.16
    chloroform 804.37
    n-propyl acetate 117.37
    acetic acid 96.56
    dichloromethane 749.3
    cyclohexanone 308.35
    propylene glycol 58.04
    isopropyl acetate 91.69
    DMAc 511.57
    2-ethoxyethanol 223.95
    isopentanol 36.01
    n-heptane 12.88
    ethyl formate 106.67
    1,2-dichloroethane 387.18
    n-hexanol 47.97
    2-methoxyethanol 273.74
    isobutyl acetate 87.43
    tetrachloromethane 52.96
    n-pentyl acetate 71.76
    transcutol 843.84
    n-heptanol 32.19
    ethylbenzene 77.47
    MIBK 90.13
    2-propoxyethanol 169.84
    tert-butanol 54.02
    MTBE 89.3
    2-butoxyethanol 97.7
    propionic acid 75.35
    o-xylene 101.4
    formic acid 34.51
    diethyl ether 114.57
    m-xylene 83.86
    p-xylene 91.11
    chlorobenzene 217.72
    dimethyl carbonate 101.76
    n-octane 7.38
    formamide 91.28
    cyclopentanone 354.3
    2-pentanone 131.74
    anisole 232.53
    cyclopentyl methyl ether 218.48
    gamma-butyrolactone 348.9
    1-methoxy-2-propanol 184.69
    pyridine 540.61
    3-pentanone 149.2
    furfural 457.32
    n-dodecane 9.0
    diethylene glycol 175.39
    diisopropyl ether 36.61
    tert-amyl alcohol 60.08
    acetylacetone 249.36
    n-hexadecane 10.69
    acetophenone 212.19
    methyl propionate 170.74
    isopentyl acetate 91.87
    trichloroethylene 783.85
    n-nonanol 53.78
    cyclohexanol 85.67
    benzyl alcohol 165.13
    2-ethylhexanol 48.27
    isooctanol 32.29
    dipropyl ether 86.67
    1,2-dichlorobenzene 188.12
    ethyl lactate 73.48
    propylene carbonate 170.4
    n-methylformamide 130.61
    2-pentanol 31.48
    n-pentane 5.21
    1-propoxy-2-propanol 125.09
    1-methoxy-2-propyl acetate 159.62
    2-(2-methoxypropoxy) propanol 163.29
    mesitylene 47.38
    ε-caprolactone 228.41
    p-cymene 48.94
    epichlorohydrin 584.86
    1,1,1-trichloroethane 269.78
    2-aminoethanol 53.02
    morpholine-4-carbaldehyde 491.48
    sulfolane 395.68
    2,2,4-trimethylpentane 7.14
    2-methyltetrahydrofuran 283.15
    n-hexyl acetate 109.1
    isooctane 4.29
    2-(2-butoxyethoxy)ethanol 227.95
    sec-butyl acetate 82.52
    tert-butyl acetate 97.74
    decalin 19.63
    glycerin 104.97
    diglyme 415.39
    acrylic acid 89.75
    isopropyl myristate 58.09
    n-butyric acid 73.74
    acetyl acetate 123.98
    di(2-ethylhexyl) phthalate 59.86
    ethyl propionate 106.8
    nitromethane 312.21
    1,2-diethoxyethane 252.43
    benzonitrile 202.46
    trioctyl phosphate 35.2
    1-bromopropane 142.44
    gamma-valerolactone 538.44
    n-decanol 43.01
    triethyl phosphate 61.89
    4-methyl-2-pentanol 25.64
    propionitrile 119.08
    vinylene carbonate 202.34
    1,1,2-trichlorotrifluoroethane 393.25
    DMS 136.86
    cumene 47.82
    2-octanol 27.99
    2-hexanone 117.76
    octyl acetate 67.78
    limonene 68.09
    1,2-dimethoxyethane 422.42
    ethyl orthosilicate 59.41
    tributyl phosphate 47.53
    diacetone alcohol 122.16
    N,N-dimethylaniline 140.06
    acrylonitrile 188.18
    aniline 186.85
    1,3-propanediol 68.41
    bromobenzene 250.95
    dibromomethane 399.61
    1,1,2,2-tetrachloroethane 595.95
    2-methyl-cyclohexyl acetate 95.53
    tetrabutyl urea 76.07
    diisobutyl methanol 33.49
    2-phenylethanol 117.48
    styrene 121.48
    dioctyl adipate 89.83
    dimethyl sulfate 171.65
    ethyl butyrate 94.46
    methyl lactate 96.8
    butyl lactate 69.15
    diethyl carbonate 76.35
    propanediol butyl ether 121.95
    triethyl orthoformate 84.28
    p-tert-butyltoluene 44.31
    methyl 4-tert-butylbenzoate 124.61
    morpholine 544.04
    tert-butylamine 33.88
    n-dodecanol 36.47
    dimethoxymethane 289.41
    ethylene carbonate 152.33
    cyrene 178.45
    2-ethoxyethyl acetate 153.39
    2-ethylhexyl acetate 80.57
    1,2,4-trichlorobenzene 248.46
    4-methylpyridine 345.72
    dibutyl ether 97.23
    2,6-dimethyl-4-heptanol 33.49
    DEF 186.03
    dimethyl isosorbide 258.35
    tetrachloroethylene 307.07
    eugenol 126.14
    triacetin 175.47
    span 80 121.08
    1,4-butanediol 45.45
    1,1-dichloroethane 278.42
    2-methyl-1-pentanol 49.07
    methyl formate 128.67
    2-methyl-1-butanol 38.43
    n-decane 14.12
    butyronitrile 87.55
    3,7-dimethyl-1-octanol 60.01
    1-chlorooctane 53.2
    1-chlorotetradecane 27.11
    n-nonane 12.7
    undecane 10.79
    tert-butylcyclohexane 13.06
    cyclooctane 12.14
    cyclopentanol 87.39
    tetrahydropyran 359.83
    tert-amyl methyl ether 88.44
    2,5,8-trioxanonane 308.17
    1-hexene 29.73
    2-isopropoxyethanol 145.88
    2,2,2-trifluoroethanol 52.61
    methyl butyrate 131.0

    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