Tetramethylolglycoluril

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  • Identifiers

    CAS number
    5395-50-6

    Molecular formula
    C8H14N4O6

    SMILES
    C(N1C2C(N(C1=O)CO)N(C(=O)N2CO)CO)O

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 66.49%
    Sweet 27.95%
    Cooling 22.76%
    Fishy 22.11%
    Savory 21.47%
    Bitter 17.14%
    Nutty 16.34%
    Meaty 16.21%
    Alcoholic 14.93%
    Mint 14.13%

     

    Flavor
    Bitter 71.66%
    Odorless 45.65%
    Sweet-like 25.36%
    Bland 25.12%
    Very mild 24.36%
    Yeast 19.48%
    Nitrile 19.23%
    Alkaline 19.0%
    Bouillon 18.91%
    Bread crust 18.74%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -2.1

    pKa est.
    4.91 (weak acid)

    Molecular weight
    262.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    248°C

    Flash point

    • 314.44 ˚C est.

  • Synonyms

    • 5395-50-6
    • Tetramethylol acetylenediurea
    • Tetramethylolglycoluril
    • Fixapret 140
    • Tetrakis(hydroxymethyl)glycoluril
    • Tetramethylol acetylene diuriene
    • NSC 3319
    • Glycoluril, 1,3,4,6-tetrakis(hydroxymethyl)-
    • 3BH30G5P9H
    • GROTAN TK6
    • ACTICIDE F(N)
    • NSC-3319
    • EINECS 226-408-0
    • NSC 67452
    • NSC-67452
    • N,N',N'',N'''-Tetrakis(hydroxymethyl)glycoluril
    • AI3-22154
    • TETRAMETHYLOLACETYLENEDIUREA
    • Imidazo(4,5-d)imidazole-2,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)-
    • Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)-
    • TETRAKIS(HYDROXYMETHYL)ACETYLENEUREA
    • 2,4,6,8-TETRAKIS(HYDROXYMETHYL)GLYCOLURIL
    • 2,5-DIOXO-1,3,4,6-TETRAKIS(HYDROXYMETHYL)HEXAHYDROIMIDAZO(4,5-D)IMIDAZOLE
    • Tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)imidazo(4,5-d)imidazole-2,5(1H,3H)-dione
    • tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)imidazo[4,5-d]imidazole-2,5(1h,3h)-dione
    • TETRAHYDRO-1,3,4,6-TETRAKIS(HYDROXYMETHYL)IMIDAZOL(4,5-D)IMIDAZOLE-2,5-(1H,3H)DIONE
    • RefChem:897357
    • TETRAMETHYLOLGLYCOLURIL [INCI]
    • 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
    • C8H14N4O6
    • 1,3,4,6-tetrakis(hydroxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione
    • MFCD00043995
    • NSC3319
    • NSC67452
    • 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo-[4,5-d]imidazole-2,5(1H,3H)-dione
    • Glycoluril,3,4,6-tetrakis(hydroxymethyl)-
    • N,N'',N'''-Tetrakis(hydroxymethyl)glycoluril
    • UNII-3BH30G5P9H
    • Imidazo[4,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)-
    • tetramethylol glycoluril
    • NCIOpen2_003449
    • SCHEMBL198235
    • Tetramethylolacetylendiharnstoff
    • DTXSID8063830
    • AKOS015914920
    • FT32795
    • s10410
    • AS-15207
    • CS-0140474
    • NS00001583
    • ST50979914
    • 395T506
    • N,N',N'', N'''-Tetrakis(hydroxymethyl)glycoluril
    • Q27257006
    • {Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione,} tetrahydro-1,3,4, 6-tetrakis(hydroxymethyl)-
    • 2,5-Dioxo-1,3,4,6- tetrakis(hydroxymethyl)hexahydroimidazo[4,5-d]imidazole
    • 1,3,4,6-tetrakis(hydroxymethyl)-1,3,4,6,3a,6a-hexahydro-1,3,4,6-tetraazapental ene-2,5-dione
    • 5395-50-6

  • Applications

    Tetramethylolglycoluril (CAS 5395-50-6) is primarily used as a multifunctional crosslinking agent for polymer dispersions and resin systems, including waterborne coatings and inks, enabling increased hardness, chemical resistance, and elevated heat stability. It commonly serves as a curing or crosslinking component in phenolic, amino, and urea-formaldehyde resin formulations, improving cure performance and mechanical properties of coatings and bonded joints. It also functions as an intermediate in the synthesis of specialty polymers and resin systems used in adhesives and composites, and can be incorporated into formulations for wood, paper, and packaging coatings and laminates, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.31
    methanol 7.16
    isopropanol 0.76
    water 72.33
    ethyl acetate 0.91
    n-propanol 0.93
    acetone 0.81
    n-butanol 0.8
    acetonitrile 1.87
    DMF 29.94
    toluene 0.21
    isobutanol 0.58
    1,4-dioxane 1.91
    methyl acetate 1.15
    THF 2.65
    2-butanone 0.85
    n-pentanol 0.48
    sec-butanol 0.62
    n-hexane 0.05
    ethylene glycol 10.83
    NMP 58.33
    cyclohexane 0.12
    DMSO 49.66
    n-butyl acetate 1.36
    n-octanol 0.42
    chloroform 1.34
    n-propyl acetate 0.55
    acetic acid 4.7
    dichloromethane 2.19
    cyclohexanone 3.2
    propylene glycol 4.56
    isopropyl acetate 0.51
    DMAc 27.56
    2-ethoxyethanol 3.87
    isopentanol 0.55
    n-heptane 0.13
    ethyl formate 2.58
    1,2-dichloroethane 1.35
    n-hexanol 0.83
    2-methoxyethanol 12.46
    isobutyl acetate 0.26
    tetrachloromethane 0.55
    n-pentyl acetate 0.68
    transcutol 2.0
    n-heptanol 0.66
    ethylbenzene 0.15
    MIBK 0.48
    2-propoxyethanol 6.37
    tert-butanol 0.7
    MTBE 0.19
    2-butoxyethanol 2.96
    propionic acid 3.23
    o-xylene 0.34
    formic acid 47.6
    diethyl ether 0.34
    m-xylene 0.25
    p-xylene 0.24
    chlorobenzene 0.36
    dimethyl carbonate 2.91
    n-octane 0.06
    formamide 45.47
    cyclopentanone 4.57
    2-pentanone 0.75
    anisole 0.26
    cyclopentyl methyl ether 0.99
    gamma-butyrolactone 12.55
    1-methoxy-2-propanol 6.13
    pyridine 2.25
    3-pentanone 0.86
    furfural 16.1
    n-dodecane 0.03
    diethylene glycol 14.67
    diisopropyl ether 0.12
    tert-amyl alcohol 0.67
    acetylacetone 1.32
    n-hexadecane 0.04
    acetophenone 0.89
    methyl propionate 2.15
    isopentyl acetate 0.93
    trichloroethylene 2.36
    n-nonanol 0.4
    cyclohexanol 1.06
    benzyl alcohol 0.88
    2-ethylhexanol 0.54
    isooctanol 0.44
    dipropyl ether 0.61
    1,2-dichlorobenzene 0.66
    ethyl lactate 2.6
    propylene carbonate 6.05
    n-methylformamide 18.27
    2-pentanol 0.41
    n-pentane 0.06
    1-propoxy-2-propanol 3.83
    1-methoxy-2-propyl acetate 2.78
    2-(2-methoxypropoxy) propanol 2.06
    mesitylene 0.21
    ε-caprolactone 4.46
    p-cymene 0.35
    epichlorohydrin 4.62
    1,1,1-trichloroethane 0.52
    2-aminoethanol 6.8
    morpholine-4-carbaldehyde 23.63
    sulfolane 33.63
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.18
    n-hexyl acetate 0.62
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 2.03
    sec-butyl acetate 0.28
    tert-butyl acetate 0.45
    decalin 0.05
    glycerin 22.76
    diglyme 4.15
    acrylic acid 6.14
    isopropyl myristate 0.26
    n-butyric acid 2.7
    acetyl acetate 0.87
    di(2-ethylhexyl) phthalate 0.69
    ethyl propionate 0.75
    nitromethane 11.57
    1,2-diethoxyethane 0.56
    benzonitrile 1.46
    trioctyl phosphate 0.7
    1-bromopropane 0.4
    gamma-valerolactone 12.69
    n-decanol 0.3
    triethyl phosphate 1.55
    4-methyl-2-pentanol 0.27
    propionitrile 1.35
    vinylene carbonate 7.03
    1,1,2-trichlorotrifluoroethane 15.43
    DMS 1.37
    cumene 0.14
    2-octanol 0.32
    2-hexanone 0.43
    octyl acetate 0.4
    limonene 0.41
    1,2-dimethoxyethane 3.17
    ethyl orthosilicate 1.08
    tributyl phosphate 0.71
    diacetone alcohol 1.79
    N,N-dimethylaniline 0.49
    acrylonitrile 3.32
    aniline 0.76
    1,3-propanediol 5.92
    bromobenzene 0.3
    dibromomethane 1.0
    1,1,2,2-tetrachloroethane 2.19
    2-methyl-cyclohexyl acetate 0.94
    tetrabutyl urea 1.33
    diisobutyl methanol 0.36
    2-phenylethanol 1.24
    styrene 0.13
    dioctyl adipate 0.52
    dimethyl sulfate 12.11
    ethyl butyrate 1.1
    methyl lactate 8.61
    butyl lactate 1.88
    diethyl carbonate 1.1
    propanediol butyl ether 2.35
    triethyl orthoformate 1.19
    p-tert-butyltoluene 0.31
    methyl 4-tert-butylbenzoate 1.63
    morpholine 3.19
    tert-butylamine 0.31
    n-dodecanol 0.22
    dimethoxymethane 5.43
    ethylene carbonate 4.87
    cyrene 6.9
    2-ethoxyethyl acetate 0.99
    2-ethylhexyl acetate 0.84
    1,2,4-trichlorobenzene 0.9
    4-methylpyridine 1.56
    dibutyl ether 0.22
    2,6-dimethyl-4-heptanol 0.36
    DEF 4.19
    dimethyl isosorbide 5.09
    tetrachloroethylene 1.96
    eugenol 2.0
    triacetin 1.06
    span 80 1.69
    1,4-butanediol 2.63
    1,1-dichloroethane 0.48
    2-methyl-1-pentanol 0.36
    methyl formate 10.76
    2-methyl-1-butanol 0.57
    n-decane 0.06
    butyronitrile 1.08
    3,7-dimethyl-1-octanol 0.35
    1-chlorooctane 0.17
    1-chlorotetradecane 0.07
    n-nonane 0.06
    undecane 0.04
    tert-butylcyclohexane 0.03
    cyclooctane 0.07
    cyclopentanol 1.67
    tetrahydropyran 0.77
    tert-amyl methyl ether 0.31
    2,5,8-trioxanonane 2.92
    1-hexene 0.11
    2-isopropoxyethanol 1.49
    2,2,2-trifluoroethanol 13.29
    methyl butyrate 1.13

    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