2,2'-Thiodiethanol bis(3-aminocrotonate)

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  • Identifiers

    CAS number
    13560-49-1

    Molecular formula
    C12H20N2O4S

    SMILES
    C/C(=C\C(=O)OCCSCCOC(=O)/C=C(/C)\N)/N

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Meaty 53.2%
    Fruity 42.31%
    Sulfurous 41.29%
    Sweet 39.37%
    Roasted 38.49%
    Savory 35.03%
    Tropical 33.51%
    Grape 28.34%
    Cooked 28.25%
    Grapefruit 26.4%

     

    Flavor
    Fruity 35.42%
    Cooked 28.69%
    Odorless 28.18%
    Roasted 26.42%
    Mild 21.57%
    Nutty 21.42%
    Taco 21.28%
    Cabbage 20.88%
    Matches 20.7%
    Acrid 20.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    6.24 (neutral)

    Molecular weight
    288.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    314°C

    Flash point

    • 208.81 ˚C est.

  • Synonyms

    • Advastab A 70
    • EINECS 236-946-8
    • Thiodiethylene beta-aminocrotonate
    • NV4QFI538P
    • 13560-49-1
    • Thiodiethylene glycol bis(beta-aminocrotonate)
    • Crotonic acid, 3-amino-, thiodiethylene ester
    • Ethanol, 2,2'-thiodi-, bis(3-aminocrotonate)
    • 2,2'-Thiodiethanol bis(3-aminocrotonate)
    • 2-Butenoic acid, 3-amino-, thiodi-2,1-ethanediyl ester
    • 3-Thia-1,5-pentanediol bis(beta-aminocrotonate)
    • Thiodiethane-1,2-diyl bis(3-aminobut-2-enoate)
    • 2-Butenoic acid, 3-amino-, 1,1'-(thiodi-2,1-ethanediyl) ester
    • DTXSID801014773
    • THIODIETHYLENE .BETA.-AMINOCROTONATE
    • THIODIETHYLENE GLYCOL BIS(.BETA.-AMINOCROTONATE)
    • 3-THIA-1,5-PENTANEDIOL BIS(.BETA.-AMINOCROTONATE)
    • RefChem:440356
    • DTXCID901471536
    • 236-946-8
    • Thiodiglycol bis(3-aminocrotonate)
    • UNII-NV4QFI538P
    • 2-[2-[(E)-3-aminobut-2-enoyl]oxyethylsulfanyl]ethyl (Z)-3-aminobut-2-enoate
    • 3-Thia-1,5-pentanediol bis(3-aminocrotonate)
    • GZVBGWRBVGVPLI-FKJILZIQSA-N
    • Q27285066
    • 2-[(2-{[(2E)-3-Aminobut-2-enoyl]oxy}ethyl)sulfanyl]ethyl (2Z)-3-aminobut-2-enoate
    • 13560-49-1

  • Applications

    2,2'-Thiodiethanol bis(3-aminocrotonate) is used as a multifunctional curing and crosslinking component in polymer and coating formulations. In industrial manufacturing, it can act as a reactive hardener for epoxy and polyurethane systems, enabling higher crosslink density and improved thermal and chemical resistance. It also serves as a reactive monomer/additive to tailor polymer networks and to introduce amino and crotonate functionality into specialty polymers and plastics. In coatings and inks, it functions as a crosslinking agent that enhances film properties and adhesion. In electronics-related materials, it may be explored as a precursor for specialty polymers or encapsulants with enhanced dimensional stability. As an intermediate in chemical synthesis, it can be used to introduce bifunctionality into formulations. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 36.56
    methanol 91.96
    isopropanol 12.1
    water 17.84
    ethyl acetate 4.79
    n-propanol 19.01
    acetone 41.18
    n-butanol 11.43
    acetonitrile 12.42
    DMF 222.72
    toluene 2.71
    isobutanol 9.46
    1,4-dioxane 9.03
    methyl acetate 10.19
    THF 61.72
    2-butanone 17.34
    n-pentanol 8.64
    sec-butanol 8.28
    n-hexane 0.27
    ethylene glycol 28.14
    NMP 198.23
    cyclohexane 0.46
    DMSO 293.52
    n-butyl acetate 4.75
    n-octanol 3.23
    chloroform 17.11
    n-propyl acetate 6.37
    acetic acid 132.68
    dichloromethane 18.13
    cyclohexanone 36.57
    propylene glycol 43.59
    isopropyl acetate 3.37
    DMAc 207.95
    2-ethoxyethanol 34.6
    isopentanol 6.3
    n-heptane 0.23
    ethyl formate 15.82
    1,2-dichloroethane 11.47
    n-hexanol 4.88
    2-methoxyethanol 81.27
    isobutyl acetate 4.24
    tetrachloromethane 2.01
    n-pentyl acetate 4.25
    transcutol 44.6
    n-heptanol 3.65
    ethylbenzene 1.33
    MIBK 6.45
    2-propoxyethanol 25.96
    tert-butanol 8.35
    MTBE 1.81
    2-butoxyethanol 14.98
    propionic acid 39.98
    o-xylene 2.18
    formic acid 158.18
    diethyl ether 1.9
    m-xylene 2.03
    p-xylene 2.26
    chlorobenzene 4.4
    dimethyl carbonate 11.25
    n-octane 0.13
    formamide 131.2
    cyclopentanone 70.35
    2-pentanone 10.61
    anisole 4.3
    cyclopentyl methyl ether 9.77
    gamma-butyrolactone 84.0
    1-methoxy-2-propanol 44.12
    pyridine 20.62
    3-pentanone 7.79
    furfural 80.61
    n-dodecane 0.11
    diethylene glycol 35.72
    diisopropyl ether 0.49
    tert-amyl alcohol 6.49
    acetylacetone 18.45
    n-hexadecane 0.13
    acetophenone 12.23
    methyl propionate 11.7
    isopentyl acetate 4.4
    trichloroethylene 30.08
    n-nonanol 3.13
    cyclohexanol 9.68
    benzyl alcohol 13.84
    2-ethylhexanol 2.56
    isooctanol 2.75
    dipropyl ether 2.2
    1,2-dichlorobenzene 5.21
    ethyl lactate 13.79
    propylene carbonate 34.81
    n-methylformamide 92.64
    2-pentanol 3.67
    n-pentane 0.26
    1-propoxy-2-propanol 14.55
    1-methoxy-2-propyl acetate 10.19
    2-(2-methoxypropoxy) propanol 17.71
    mesitylene 1.19
    ε-caprolactone 29.45
    p-cymene 1.27
    epichlorohydrin 50.35
    1,1,1-trichloroethane 6.15
    2-aminoethanol 43.72
    morpholine-4-carbaldehyde 81.52
    sulfolane 161.66
    2,2,4-trimethylpentane 0.15
    2-methyltetrahydrofuran 13.88
    n-hexyl acetate 5.63
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 20.73
    sec-butyl acetate 2.97
    tert-butyl acetate 4.53
    decalin 0.24
    glycerin 81.63
    diglyme 32.78
    acrylic acid 60.67
    isopropyl myristate 2.05
    n-butyric acid 29.17
    acetyl acetate 5.97
    di(2-ethylhexyl) phthalate 6.49
    ethyl propionate 5.12
    nitromethane 119.94
    1,2-diethoxyethane 4.39
    benzonitrile 10.39
    trioctyl phosphate 3.8
    1-bromopropane 3.47
    gamma-valerolactone 95.51
    n-decanol 2.21
    triethyl phosphate 4.69
    4-methyl-2-pentanol 2.22
    propionitrile 8.1
    vinylene carbonate 33.69
    1,1,2-trichlorotrifluoroethane 92.5
    DMS 7.43
    cumene 1.17
    2-octanol 1.91
    2-hexanone 8.3
    octyl acetate 3.35
    limonene 1.74
    1,2-dimethoxyethane 30.77
    ethyl orthosilicate 3.69
    tributyl phosphate 4.61
    diacetone alcohol 18.3
    N,N-dimethylaniline 4.9
    acrylonitrile 18.14
    aniline 8.76
    1,3-propanediol 37.27
    bromobenzene 2.91
    dibromomethane 9.18
    1,1,2,2-tetrachloroethane 24.69
    2-methyl-cyclohexyl acetate 6.43
    tetrabutyl urea 8.47
    diisobutyl methanol 1.39
    2-phenylethanol 9.19
    styrene 1.69
    dioctyl adipate 5.72
    dimethyl sulfate 37.15
    ethyl butyrate 4.76
    methyl lactate 29.62
    butyl lactate 10.47
    diethyl carbonate 3.81
    propanediol butyl ether 20.04
    triethyl orthoformate 4.16
    p-tert-butyltoluene 1.16
    methyl 4-tert-butylbenzoate 12.58
    morpholine 22.18
    tert-butylamine 2.49
    n-dodecanol 1.54
    dimethoxymethane 35.32
    ethylene carbonate 21.87
    cyrene 40.73
    2-ethoxyethyl acetate 7.4
    2-ethylhexyl acetate 3.36
    1,2,4-trichlorobenzene 7.67
    4-methylpyridine 15.5
    dibutyl ether 1.72
    2,6-dimethyl-4-heptanol 1.39
    DEF 20.38
    dimethyl isosorbide 32.61
    tetrachloroethylene 15.54
    eugenol 16.28
    triacetin 12.72
    span 80 15.74
    1,4-butanediol 17.38
    1,1-dichloroethane 6.44
    2-methyl-1-pentanol 5.45
    methyl formate 66.12
    2-methyl-1-butanol 7.33
    n-decane 0.19
    butyronitrile 7.77
    3,7-dimethyl-1-octanol 2.58
    1-chlorooctane 0.95
    1-chlorotetradecane 0.41
    n-nonane 0.17
    undecane 0.14
    tert-butylcyclohexane 0.19
    cyclooctane 0.17
    cyclopentanol 19.26
    tetrahydropyran 8.04
    tert-amyl methyl ether 2.23
    2,5,8-trioxanonane 27.14
    1-hexene 1.11
    2-isopropoxyethanol 15.57
    2,2,2-trifluoroethanol 54.66
    methyl butyrate 9.65

    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