2-Methyl-1,3-dithiolane

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  • Identifiers

    CAS number
    5616-51-3

    Molecular formula
    C4H8S2

    SMILES
    CC1SCCS1

  • Odor profile

    Fragrance
    Sulfurous 80.92%
    Onion 51.93%
    Meaty 50.34%
    Alliaceous 49.89%
    Garlic 46.24%
    Savory 33.28%
    Roasted 31.8%
    Cooked 30.05%
    Vegetable 28.17%
    Beefy 26.11%

     

    Flavor
    Sulfurous 69.06%
    Alliaceous 47.56%
    Onion 45.13%
    Meaty 39.69%
    Roasted 39.52%
    Vegetable 39.26%
    Sulfur 38.98%
    Garlic 38.59%
    Savory 32.87%
    Cabbage 30.3%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    4.14 (weak acid)

    Molecular weight
    120.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point

    • 65.00 °C. @ 10.00 mm Hg

    Flash point

    • 64.38 ˚C est.

    Solubility expt.

    • insoluble in water; slightly soluble in fat

  • Synonyms

    • 2-Methyl-1,3-dithiolane
    • 5616-51-3
    • 1,3-DITHIOLANE, 2-METHYL-
    • 2-Methyl-1,3-dithiacyclopentane
    • FEMA No. 3705
    • EINECS 227-038-2
    • UNII-4O81R0SPR0
    • 1,3-Dithiolane,2-methyl-
    • NSC 227863
    • 4O81R0SPR0
    • NSC-227863
    • DTXSID8063963
    • 2-METHYL-1,3-DITHIOLANE [FHFI]
    • MFCD01729666
    • NSC227863
    • SCHEMBL761708
    • Acetaldehdye ethylene thioacetal
    • DTXCID6042028
    • FEMA 3705
    • 2-Methyl-1,3-dithiolane, AldrichCPR
    • AKOS025396842
    • AS-81346
    • CS-0365126
    • NS00022383
    • F75650
    • Q27260281
    • 227-038-2

  • Applications

    2-Methyl-1,3-dithiolane (CAS 5616-51-3) is primarily used as a carbonyl-protecting group in organic synthesis. It forms a cyclic thioacetal with aldehydes or ketones, masking the carbonyl functionality to enable multi-step syntheses. The resulting dithiolane derivatives serve as masked carbonyls for strategic C–C bond formation and umpolung-type transformations when deprotonated to generate an acyl anion equivalent. In industry, the compound is employed as an intermediate and building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. The 2-methyl substituent can influence reactivity and selectivity in downstream transformations, making these derivatives useful in organosulfur and heterocyclic chemistry. They are typically handled under appropriate controls and subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 253.11
    methanol 200.02
    isopropanol 200.32
    water 2.16
    ethyl acetate 573.64
    n-propanol 235.86
    acetone 456.14
    n-butanol 257.85
    acetonitrile 386.97
    DMF 372.24
    toluene 355.71
    isobutanol 169.76
    1,4-dioxane 816.11
    methyl acetate 471.22
    THF 837.78
    2-butanone 426.6
    n-pentanol 164.49
    sec-butanol 222.12
    n-hexane 40.9
    ethylene glycol 81.68
    NMP 417.79
    cyclohexane 115.87
    DMSO 349.54
    n-butyl acetate 516.75
    n-octanol 193.54
    chloroform 1402.59
    n-propyl acetate 311.47
    acetic acid 377.56
    dichloromethane 906.15
    cyclohexanone 618.17
    propylene glycol 130.13
    isopropyl acetate 348.23
    DMAc 399.72
    2-ethoxyethanol 316.78
    isopentanol 211.47
    n-heptane 90.1
    ethyl formate 306.94
    1,2-dichloroethane 498.72
    n-hexanol 276.29
    2-methoxyethanol 417.85
    isobutyl acetate 208.2
    tetrachloromethane 346.53
    n-pentyl acetate 302.66
    transcutol 1109.15
    n-heptanol 208.08
    ethylbenzene 147.71
    MIBK 255.86
    2-propoxyethanol 457.56
    tert-butanol 254.38
    MTBE 301.08
    2-butoxyethanol 337.21
    propionic acid 312.15
    o-xylene 203.46
    formic acid 109.88
    diethyl ether 395.72
    m-xylene 230.48
    p-xylene 194.55
    chlorobenzene 470.08
    dimethyl carbonate 210.73
    n-octane 35.97
    formamide 182.87
    cyclopentanone 676.05
    2-pentanone 382.01
    anisole 368.14
    cyclopentyl methyl ether 425.41
    gamma-butyrolactone 714.75
    1-methoxy-2-propanol 359.54
    pyridine 710.68
    3-pentanone 329.07
    furfural 801.88
    n-dodecane 29.46
    diethylene glycol 310.24
    diisopropyl ether 167.22
    tert-amyl alcohol 244.28
    acetylacetone 501.28
    n-hexadecane 34.04
    acetophenone 316.8
    methyl propionate 364.16
    isopentyl acetate 374.3
    trichloroethylene 1197.62
    n-nonanol 184.94
    cyclohexanol 262.57
    benzyl alcohol 239.25
    2-ethylhexanol 225.18
    isooctanol 165.05
    dipropyl ether 323.1
    1,2-dichlorobenzene 442.41
    ethyl lactate 158.17
    propylene carbonate 494.34
    n-methylformamide 236.45
    2-pentanol 211.82
    n-pentane 62.52
    1-propoxy-2-propanol 412.46
    1-methoxy-2-propyl acetate 458.03
    2-(2-methoxypropoxy) propanol 307.92
    mesitylene 158.9
    ε-caprolactone 568.89
    p-cymene 169.13
    epichlorohydrin 690.32
    1,1,1-trichloroethane 746.42
    2-aminoethanol 148.1
    morpholine-4-carbaldehyde 575.73
    sulfolane 589.29
    2,2,4-trimethylpentane 42.68
    2-methyltetrahydrofuran 576.96
    n-hexyl acetate 333.17
    isooctane 37.29
    2-(2-butoxyethoxy)ethanol 430.62
    sec-butyl acetate 239.74
    tert-butyl acetate 390.18
    decalin 53.75
    glycerin 187.6
    diglyme 803.82
    acrylic acid 269.8
    isopropyl myristate 166.52
    n-butyric acid 464.16
    acetyl acetate 469.47
    di(2-ethylhexyl) phthalate 140.14
    ethyl propionate 281.6
    nitromethane 635.2
    1,2-diethoxyethane 507.77
    benzonitrile 389.22
    trioctyl phosphate 103.76
    1-bromopropane 319.57
    gamma-valerolactone 779.7
    n-decanol 138.06
    triethyl phosphate 176.64
    4-methyl-2-pentanol 146.52
    propionitrile 317.49
    vinylene carbonate 532.2
    1,1,2-trichlorotrifluoroethane 560.44
    DMS 261.59
    cumene 108.8
    2-octanol 141.66
    2-hexanone 279.67
    octyl acetate 200.29
    limonene 235.01
    1,2-dimethoxyethane 470.5
    ethyl orthosilicate 178.28
    tributyl phosphate 128.22
    diacetone alcohol 351.75
    N,N-dimethylaniline 200.97
    acrylonitrile 378.13
    aniline 368.25
    1,3-propanediol 221.24
    bromobenzene 503.87
    dibromomethane 617.28
    1,1,2,2-tetrachloroethane 843.57
    2-methyl-cyclohexyl acetate 264.98
    tetrabutyl urea 143.93
    diisobutyl methanol 159.39
    2-phenylethanol 301.14
    styrene 198.53
    dioctyl adipate 219.37
    dimethyl sulfate 258.85
    ethyl butyrate 389.61
    methyl lactate 193.93
    butyl lactate 225.5
    diethyl carbonate 274.69
    propanediol butyl ether 278.21
    triethyl orthoformate 313.66
    p-tert-butyltoluene 174.3
    methyl 4-tert-butylbenzoate 300.39
    morpholine 682.08
    tert-butylamine 179.16
    n-dodecanol 106.47
    dimethoxymethane 360.95
    ethylene carbonate 427.93
    cyrene 274.81
    2-ethoxyethyl acetate 414.13
    2-ethylhexyl acetate 323.95
    1,2,4-trichlorobenzene 519.71
    4-methylpyridine 561.47
    dibutyl ether 274.92
    2,6-dimethyl-4-heptanol 159.39
    DEF 360.62
    dimethyl isosorbide 503.56
    tetrachloroethylene 616.24
    eugenol 279.81
    triacetin 370.91
    span 80 307.79
    1,4-butanediol 96.83
    1,1-dichloroethane 596.49
    2-methyl-1-pentanol 157.25
    methyl formate 211.54
    2-methyl-1-butanol 194.81
    n-decane 50.92
    butyronitrile 341.69
    3,7-dimethyl-1-octanol 192.32
    1-chlorooctane 152.35
    1-chlorotetradecane 70.39
    n-nonane 49.3
    undecane 37.1
    tert-butylcyclohexane 48.16
    cyclooctane 56.21
    cyclopentanol 256.39
    tetrahydropyran 615.02
    tert-amyl methyl ether 246.88
    2,5,8-trioxanonane 536.45
    1-hexene 121.21
    2-isopropoxyethanol 251.41
    2,2,2-trifluoroethanol 203.47
    methyl butyrate 325.13

    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