cis-2,3-Dimethylthiirane

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  • Identifiers

    CAS number
    5954-71-2

    Molecular formula
    C4H8S

    SMILES
    C[C@@H]1[C@@H](S1)C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sulfurous 79.86%
    Meaty 74.52%
    Roasted 56.3%
    Onion 55.5%
    Alliaceous 48.21%
    Savory 44.24%
    Garlic 39.95%
    Beefy 39.77%
    Cooked 37.61%
    Vegetable 35.03%

     

    Flavor
    Sulfurous 56.49%
    Meaty 36.87%
    Onion 33.58%
    Green 29.25%
    Tropical 27.42%
    Sulfury 27.07%
    Roasted 26.97%
    Alliaceous 26.17%
    Vegetable 25.98%
    Bouillon 22.91%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    4.78 (weak acid)

    Molecular weight
    88.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    88°C

    Flash point

    • 9.13 ˚C est.

  • Synonyms

    • cis-2,3-Dimethylthiirane
    • (2r,3s)-2,3-dimethylthiirane
    • Thiirane, 2,3-dimethyl-, cis-
    • Thiirane, 2,3-dimethyl-, (2R,3S)-rel-
    • EINECS 227-721-5
    • DTXSID40884205
    • RefChem:126390
    • DTXCID501023660
    • 227-721-5
    • 5954-71-2
    • cis-Dimethylthiirane
    • cis-2-Butene sulfide
    • cisdimethylthiirane
    • cis-2-Butene episulfide
    • Z-2,3-Dimethyl-thiirane
    • cis-2,3-Dimethylepisulfide
    • 2,3-Dimethyl-cis-Thiirane
    • SCHEMBL2116781
    • ZMJBHCIEMIVIFZ-ZXZARUISSA-N
    • 2,3-Dimethyl-(2R,3S)-rel-Thiirane
    • DB-254239
    • NS00047452
    • 5954-71-2

  • Applications

    cis-2,3-Dimethylthiirane (CAS 5954-71-2) is primarily used as an organic-synthesis intermediate, enabling the preparation of sulfur-containing heterocycles and other organosulfur compounds. It serves as a building block in pharmaceutical and agrochemical research and development, providing routes to sulfur-functionalized motifs. In polymer and materials chemistry, it can be employed as a precursor for sulfur-containing polymers or as a reactive feedstock for further transformations. It also functions as a reagent in synthetic-method development and ring-opening/ring-expansion chemistry in R&D settings, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 75.07
    methanol 50.23
    isopropanol 65.87
    water 0.32
    ethyl acetate 168.82
    n-propanol 72.41
    acetone 130.22
    n-butanol 76.73
    acetonitrile 109.2
    DMF 88.98
    toluene 86.18
    isobutanol 51.95
    1,4-dioxane 204.15
    methyl acetate 143.35
    THF 315.67
    2-butanone 155.51
    n-pentanol 58.51
    sec-butanol 72.29
    n-hexane 25.48
    ethylene glycol 18.5
    NMP 125.53
    cyclohexane 44.08
    DMSO 92.46
    n-butyl acetate 162.31
    n-octanol 58.59
    chloroform 384.02
    n-propyl acetate 102.56
    acetic acid 101.84
    dichloromethane 235.23
    cyclohexanone 180.73
    propylene glycol 37.09
    isopropyl acetate 113.38
    DMAc 120.44
    2-ethoxyethanol 88.15
    isopentanol 61.83
    n-heptane 45.64
    ethyl formate 77.01
    1,2-dichloroethane 128.94
    n-hexanol 101.43
    2-methoxyethanol 106.66
    isobutyl acetate 68.46
    tetrachloromethane 88.75
    n-pentyl acetate 92.25
    transcutol 314.04
    n-heptanol 64.96
    ethylbenzene 50.03
    MIBK 84.6
    2-propoxyethanol 151.15
    tert-butanol 86.43
    MTBE 109.87
    2-butoxyethanol 110.15
    propionic acid 87.24
    o-xylene 59.56
    formic acid 23.83
    diethyl ether 131.01
    m-xylene 60.13
    p-xylene 63.98
    chlorobenzene 111.99
    dimethyl carbonate 48.35
    n-octane 16.19
    formamide 40.61
    cyclopentanone 227.96
    2-pentanone 129.63
    anisole 106.97
    cyclopentyl methyl ether 146.93
    gamma-butyrolactone 212.61
    1-methoxy-2-propanol 111.63
    pyridine 185.94
    3-pentanone 116.85
    furfural 195.36
    n-dodecane 10.99
    diethylene glycol 81.02
    diisopropyl ether 62.23
    tert-amyl alcohol 83.79
    acetylacetone 142.13
    n-hexadecane 12.51
    acetophenone 97.74
    methyl propionate 112.05
    isopentyl acetate 123.39
    trichloroethylene 283.33
    n-nonanol 56.42
    cyclohexanol 74.19
    benzyl alcohol 68.99
    2-ethylhexanol 80.5
    isooctanol 52.91
    dipropyl ether 136.0
    1,2-dichlorobenzene 102.49
    ethyl lactate 52.73
    propylene carbonate 137.7
    n-methylformamide 53.28
    2-pentanol 69.62
    n-pentane 28.42
    1-propoxy-2-propanol 151.92
    1-methoxy-2-propyl acetate 157.38
    2-(2-methoxypropoxy) propanol 92.58
    mesitylene 42.36
    ε-caprolactone 166.6
    p-cymene 57.74
    epichlorohydrin 207.62
    1,1,1-trichloroethane 206.04
    2-aminoethanol 37.93
    morpholine-4-carbaldehyde 140.59
    sulfolane 175.84
    2,2,4-trimethylpentane 17.58
    2-methyltetrahydrofuran 219.09
    n-hexyl acetate 106.15
    isooctane 15.5
    2-(2-butoxyethoxy)ethanol 129.85
    sec-butyl acetate 84.44
    tert-butyl acetate 127.92
    decalin 22.52
    glycerin 46.31
    diglyme 225.82
    acrylic acid 73.33
    isopropyl myristate 54.67
    n-butyric acid 119.37
    acetyl acetate 124.44
    di(2-ethylhexyl) phthalate 41.76
    ethyl propionate 98.92
    nitromethane 145.62
    1,2-diethoxyethane 159.41
    benzonitrile 97.89
    trioctyl phosphate 32.1
    1-bromopropane 110.68
    gamma-valerolactone 222.0
    n-decanol 42.37
    triethyl phosphate 61.34
    4-methyl-2-pentanol 47.22
    propionitrile 99.59
    vinylene carbonate 118.7
    1,1,2-trichlorotrifluoroethane 154.57
    DMS 80.91
    cumene 37.97
    2-octanol 44.67
    2-hexanone 102.9
    octyl acetate 62.4
    limonene 79.71
    1,2-dimethoxyethane 139.43
    ethyl orthosilicate 61.6
    tributyl phosphate 39.4
    diacetone alcohol 114.93
    N,N-dimethylaniline 64.9
    acrylonitrile 99.38
    aniline 88.39
    1,3-propanediol 54.66
    bromobenzene 117.92
    dibromomethane 180.8
    1,1,2,2-tetrachloroethane 230.71
    2-methyl-cyclohexyl acetate 94.09
    tetrabutyl urea 46.56
    diisobutyl methanol 59.95
    2-phenylethanol 94.37
    styrene 61.32
    dioctyl adipate 65.96
    dimethyl sulfate 59.67
    ethyl butyrate 138.78
    methyl lactate 58.26
    butyl lactate 68.71
    diethyl carbonate 89.81
    propanediol butyl ether 80.5
    triethyl orthoformate 106.5
    p-tert-butyltoluene 59.92
    methyl 4-tert-butylbenzoate 88.73
    morpholine 196.51
    tert-butylamine 61.9
    n-dodecanol 32.76
    dimethoxymethane 86.75
    ethylene carbonate 100.8
    cyrene 86.2
    2-ethoxyethyl acetate 123.15
    2-ethylhexyl acetate 108.28
    1,2,4-trichlorobenzene 127.36
    4-methylpyridine 137.97
    dibutyl ether 93.57
    2,6-dimethyl-4-heptanol 59.95
    DEF 109.93
    dimethyl isosorbide 166.12
    tetrachloroethylene 154.63
    eugenol 81.44
    triacetin 108.08
    span 80 91.64
    1,4-butanediol 26.02
    1,1-dichloroethane 181.73
    2-methyl-1-pentanol 56.21
    methyl formate 47.95
    2-methyl-1-butanol 59.65
    n-decane 19.55
    butyronitrile 101.27
    3,7-dimethyl-1-octanol 61.01
    1-chlorooctane 52.62
    1-chlorotetradecane 23.9
    n-nonane 19.66
    undecane 14.05
    tert-butylcyclohexane 22.03
    cyclooctane 22.2
    cyclopentanol 84.22
    tetrahydropyran 202.69
    tert-amyl methyl ether 91.92
    2,5,8-trioxanonane 148.78
    1-hexene 60.67
    2-isopropoxyethanol 78.43
    2,2,2-trifluoroethanol 47.41
    methyl butyrate 108.0

    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