Oxiranemethanol, 3,3'-(1,3-butadiyne-1,4-diyl)bis-, (2R,2'R,3R,3'R)-

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  • Identifiers

    CAS number
    147921-90-2

    Molecular formula
    C10H10O4

    SMILES
    C(C1C(O1)C#CC#CC2C(O2)CO)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 47.06%
    Sweet 26.82%
    Meaty 20.85%
    Savory 20.15%
    Cooked 14.09%
    Roasted 13.96%
    Fishy 13.66%
    Alcoholic 11.9%
    Milky 11.65%
    Clean 10.77%

     

    Flavor
    Bitter 88.66%
    Odorless 30.64%
    Bland 28.49%
    Sweet-like 21.07%
    Nitrile 17.34%
    Cedarleaf 16.84%
    Alkaline 16.18%
    Oriental 16.13%
    Rotten 15.92%
    Bouillon 15.91%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.2

    pKa est.
    3.86 (weak acid)

    Molecular weight
    194.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    553°C

    Melting point expt.

    • 168 - 169 °C

    Flash point

    • 199.82 ˚C est.

  • Synonyms

    • Repandiol
    • 147921-90-2
    • 2,3,8,9-Diepoxy-4,6-decadiyne-1,10-diol
    • (3-{4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-2-yl)methanol
    • (3-(4-(3-(hydroxymethyl)oxiran-2-yl)buta-1,3-diyn-1-yl)oxiran-2-yl)methanol
    • RefChem:928370
    • Oxiranemethanol, 3,3'-(1,3-butadiyne-1,4-diyl)bis-, (2R,2'R,3R,3'R)-
    • [3-[4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diynyl]oxiran-2-yl]methanol
    • SCHEMBL28660087
    • DTXSID60933249
    • CHEBI:166496
    • 2,3:8,9-Dianhydro-4,5,6,7-tetradeoxydeca-4,6-diynitol
    • Oxiranemethanol, 3,3'-(1,3-butadiyne-1,4-diyl)bis-, (2R-(2alpha,3beta(2'R*,3'R*)))-
    • 147921-90-2

  • Applications

    Oxiranemethanol, 3,3'-(1,3-butadiyne-1,4-diyl)bis-, (2R,2'R,3R,3'R)- (CAS 147921-90-2) is a multi-functional epoxy monomer featuring two glycidyl groups linked by a rigid 1,3-butadiyne core, and is primarily used as a crosslinking and chain-extending agent in epoxy resin systems to boost thermal and mechanical performance. It also serves as a reactive intermediate for the synthesis of high-performance polymers and composites and as a resin modifier in coatings and adhesives formulations. In coatings and inks, it acts as a crosslinker to produce durable, chemically resistant films; in electronics and optical materials, the diynyl linker adds rigidity and enables further functionalization, supporting encapsulants and UV-curable systems. It may also be explored as a building block for specialty polymer architectures.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.19
    methanol 32.19
    isopropanol 7.77
    water 1.25
    ethyl acetate 10.52
    n-propanol 7.41
    acetone 20.73
    n-butanol 6.87
    acetonitrile 21.67
    DMF 57.4
    toluene 1.24
    isobutanol 4.69
    1,4-dioxane 18.65
    methyl acetate 13.79
    THF 27.44
    2-butanone 11.4
    n-pentanol 6.34
    sec-butanol 6.54
    n-hexane 0.26
    ethylene glycol 28.65
    NMP 34.3
    cyclohexane 0.77
    DMSO 179.71
    n-butyl acetate 6.49
    n-octanol 2.83
    chloroform 9.69
    n-propyl acetate 8.31
    acetic acid 47.21
    dichloromethane 13.02
    cyclohexanone 12.94
    propylene glycol 18.02
    isopropyl acetate 7.25
    DMAc 66.52
    2-ethoxyethanol 44.15
    isopentanol 7.0
    n-heptane 0.6
    ethyl formate 12.78
    1,2-dichloroethane 9.77
    n-hexanol 5.16
    2-methoxyethanol 67.16
    isobutyl acetate 4.43
    tetrachloromethane 1.24
    n-pentyl acetate 3.33
    transcutol 91.08
    n-heptanol 3.18
    ethylbenzene 1.24
    MIBK 6.96
    2-propoxyethanol 22.9
    tert-butanol 11.95
    MTBE 6.33
    2-butoxyethanol 14.49
    propionic acid 13.43
    o-xylene 1.71
    formic acid 73.64
    diethyl ether 5.62
    m-xylene 1.27
    p-xylene 1.52
    chlorobenzene 1.97
    dimethyl carbonate 9.28
    n-octane 0.27
    formamide 122.05
    cyclopentanone 18.7
    2-pentanone 8.24
    anisole 6.23
    cyclopentyl methyl ether 7.12
    gamma-butyrolactone 25.0
    1-methoxy-2-propanol 35.71
    pyridine 11.36
    3-pentanone 6.81
    furfural 35.32
    n-dodecane 0.26
    diethylene glycol 44.78
    diisopropyl ether 2.08
    tert-amyl alcohol 9.71
    acetylacetone 19.71
    n-hexadecane 0.29
    acetophenone 10.33
    methyl propionate 10.3
    isopentyl acetate 6.43
    trichloroethylene 17.01
    n-nonanol 3.15
    cyclohexanol 6.9
    benzyl alcohol 9.35
    2-ethylhexanol 3.72
    isooctanol 3.08
    dipropyl ether 4.59
    1,2-dichlorobenzene 2.83
    ethyl lactate 12.84
    propylene carbonate 13.01
    n-methylformamide 37.66
    2-pentanol 4.65
    n-pentane 0.34
    1-propoxy-2-propanol 14.98
    1-methoxy-2-propyl acetate 13.53
    2-(2-methoxypropoxy) propanol 23.93
    mesitylene 1.13
    ε-caprolactone 13.56
    p-cymene 1.78
    epichlorohydrin 30.11
    1,1,1-trichloroethane 4.19
    2-aminoethanol 24.81
    morpholine-4-carbaldehyde 43.48
    sulfolane 42.69
    2,2,4-trimethylpentane 0.35
    2-methyltetrahydrofuran 10.37
    n-hexyl acetate 4.68
    isooctane 0.22
    2-(2-butoxyethoxy)ethanol 27.62
    sec-butyl acetate 5.31
    tert-butyl acetate 8.37
    decalin 0.4
    glycerin 50.87
    diglyme 54.35
    acrylic acid 19.54
    isopropyl myristate 2.99
    n-butyric acid 13.07
    acetyl acetate 10.36
    di(2-ethylhexyl) phthalate 4.4
    ethyl propionate 7.55
    nitromethane 90.9
    1,2-diethoxyethane 11.61
    benzonitrile 7.98
    trioctyl phosphate 3.02
    1-bromopropane 2.83
    gamma-valerolactone 34.88
    n-decanol 2.63
    triethyl phosphate 6.82
    4-methyl-2-pentanol 3.99
    propionitrile 10.13
    vinylene carbonate 13.31
    1,1,2-trichlorotrifluoroethane 50.05
    DMS 7.87
    cumene 1.17
    2-octanol 1.78
    2-hexanone 7.2
    octyl acetate 3.72
    limonene 2.49
    1,2-dimethoxyethane 45.33
    ethyl orthosilicate 6.11
    tributyl phosphate 3.96
    diacetone alcohol 20.61
    N,N-dimethylaniline 5.69
    acrylonitrile 17.37
    aniline 4.96
    1,3-propanediol 26.12
    bromobenzene 1.6
    dibromomethane 6.3
    1,1,2,2-tetrachloroethane 14.68
    2-methyl-cyclohexyl acetate 7.07
    tetrabutyl urea 6.46
    diisobutyl methanol 3.17
    2-phenylethanol 7.79
    styrene 1.47
    dioctyl adipate 6.69
    dimethyl sulfate 21.56
    ethyl butyrate 8.24
    methyl lactate 20.3
    butyl lactate 6.76
    diethyl carbonate 7.39
    propanediol butyl ether 14.08
    triethyl orthoformate 7.69
    p-tert-butyltoluene 1.65
    methyl 4-tert-butylbenzoate 10.6
    morpholine 24.79
    tert-butylamine 5.31
    n-dodecanol 2.15
    dimethoxymethane 27.64
    ethylene carbonate 10.32
    cyrene 24.07
    2-ethoxyethyl acetate 8.38
    2-ethylhexyl acetate 4.56
    1,2,4-trichlorobenzene 4.26
    4-methylpyridine 6.91
    dibutyl ether 3.31
    2,6-dimethyl-4-heptanol 3.17
    DEF 16.37
    dimethyl isosorbide 27.12
    tetrachloroethylene 9.16
    eugenol 12.87
    triacetin 13.64
    span 80 12.64
    1,4-butanediol 14.15
    1,1-dichloroethane 4.33
    2-methyl-1-pentanol 6.15
    methyl formate 26.68
    2-methyl-1-butanol 5.74
    n-decane 0.38
    butyronitrile 7.8
    3,7-dimethyl-1-octanol 3.81
    1-chlorooctane 1.15
    1-chlorotetradecane 0.71
    n-nonane 0.32
    undecane 0.31
    tert-butylcyclohexane 0.3
    cyclooctane 0.38
    cyclopentanol 7.13
    tetrahydropyran 8.16
    tert-amyl methyl ether 5.79
    2,5,8-trioxanonane 41.69
    1-hexene 0.83
    2-isopropoxyethanol 23.24
    2,2,2-trifluoroethanol 26.58
    methyl butyrate 10.66

    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