Trimethylsilyl ((trimethylsilyl)oxy)acetate

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  • Identifiers

    CAS number
    33581-77-0

    Molecular formula
    C8H20O3Si2

    SMILES
    C[Si](C)(C)OCC(=O)O[Si](C)(C)C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 42.09%
    Mint 32.17%
    Ethereal 24.77%
    Fermented 24.23%
    Odorless 24.12%
    Green 23.57%
    Fresh 23.09%
    Woody 22.99%
    Camphoreous 21.71%
    Herbal 21.48%

     

    Flavor
    Fruity 45.99%
    Sweet 39.9%
    Green 35.39%
    Bitter 33.0%
    Herbal 30.61%
    Citrus 29.93%
    Tropical 28.24%
    Pungent 25.35%
    Lavender 23.74%
    Banana 21.72%

     

    Odor impact est.
    Medium

  • Properties

    pKa est.
    10.17 (weak base)

    Molecular weight
    220.41 g/mol

    Flash point

    • 80.92 ˚C est.

  • Synonyms

    • 33581-77-0
    • Trimethylsilyl ((trimethylsilyl)oxy)acetate
    • EINECS 251-580-9
    • WY41M9TKT0
    • trimethylsilyl [(trimethylsilyl)oxy]acetate
    • DTXSID50187279
    • RefChem:899900
    • DTXCID10109770
    • 251-580-9
    • Trimethylsilyl trimethylsiloxyacetate
    • trimethylsilyl 2-((trimethylsilyl)oxy)acetate
    • trimethylsilyl 2-trimethylsilyloxyacetate
    • TRIMETHYLSILYL(TRIMETHYLSILOXY)ACETATE
    • MFCD00009840
    • C8H20O3Si2
    • Acetic acid, [(trimethylsilyl)oxy]-, trimethylsilyl ester
    • trimethylsilyl 2-[(trimethylsilyl)oxy]acetate
    • Acetic acid, (trimethylsiloxy)-, trimethylsilyl ester
    • UNII-WY41M9TKT0
    • trimethylsilyl (trimethylsiloxy)acetate
    • trimethylsilyl trimethylsiloxy glycolate
    • Glycolic acid, di-TMS
    • Glycolic acid, bis-TMS
    • Glycolic acid, (2TMS)
    • SCHEMBL2572442
    • Glycolic acid, 2TMS derivative
    • IBA58177
    • AKOS015966807
    • Trimethylsilyl (trimethylsilyloxy)acetate
    • trimethylsilyl-2-(trimethylsiloxy)acetate
    • AS-81759
    • SY112920
    • Trimethylsilyl trimethylsiloxyacetate, 99%
    • trimethylsilyl-2 -(trimethylsiloxy)acetate
    • DB-048450
    • (Trimethylsiloxy)acetate trimethylsilyl ester
    • CS-0158133
    • NS00058990
    • trimethylsilyl2-((trimethylsilyl)oxy)acetate
    • D82091
    • F690135
    • [(trimethylsilyl)oxy]acetic acid trimethylsilyl ester
    • Q27293025
    • Glycolic acid, trimethylsilyl ether, trimethylsilyl ester
    • 33581-77-0

  • Applications

    Trimethylsilyl ((trimethylsilyl)oxy)acetate is a silyl-protected glycolate ester used primarily as an intermediate in organic synthesis to install or preserve the glycolyl moiety as a trimethylsilyl ether. It commonly serves as a protecting-group reagent for alcohol and carboxyl functionalities, enabling multi-step transformations. The compound can act as a precursor to further silylated glycolate esters and related monomers for polymer and plastics chemistries, allowing controlled reactivity in downstream processing. In coatings and inks, it may function as a reactive intermediate or building block for silane- or ester-containing formulations. In pharmaceutical synthesis it is used as an advanced intermediate in multi-step routes, with usage governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1136.87
    methanol 1561.36
    isopropanol 706.75
    water 58.42
    ethyl acetate 264.32
    n-propanol 806.21
    acetone 492.83
    n-butanol 626.36
    acetonitrile 337.61
    DMF 857.8
    toluene 221.09
    isobutanol 430.22
    1,4-dioxane 981.48
    methyl acetate 325.44
    THF 1211.97
    2-butanone 361.19
    n-pentanol 457.58
    sec-butanol 558.11
    n-hexane 269.84
    ethylene glycol 470.69
    NMP 580.0
    cyclohexane 424.27
    DMSO 756.7
    n-butyl acetate 298.37
    n-octanol 357.16
    chloroform 839.9
    n-propyl acetate 231.29
    acetic acid 830.94
    dichloromethane 542.7
    cyclohexanone 444.3
    propylene glycol 531.82
    isopropyl acetate 193.08
    DMAc 591.09
    2-ethoxyethanol 672.97
    isopentanol 378.56
    n-heptane 221.85
    ethyl formate 328.19
    1,2-dichloroethane 408.5
    n-hexanol 579.53
    2-methoxyethanol 1114.42
    isobutyl acetate 150.77
    tetrachloromethane 215.17
    n-pentyl acetate 220.8
    transcutol 1028.89
    n-heptanol 334.0
    ethylbenzene 142.2
    MIBK 181.63
    2-propoxyethanol 834.37
    tert-butanol 557.46
    MTBE 345.4
    2-butoxyethanol 491.09
    propionic acid 480.83
    o-xylene 138.2
    formic acid 724.95
    diethyl ether 525.12
    m-xylene 140.19
    p-xylene 155.34
    chlorobenzene 228.93
    dimethyl carbonate 158.45
    n-octane 96.17
    formamide 711.29
    cyclopentanone 521.31
    2-pentanone 286.03
    anisole 244.76
    cyclopentyl methyl ether 445.22
    gamma-butyrolactone 510.87
    1-methoxy-2-propanol 727.59
    pyridine 534.54
    3-pentanone 228.41
    furfural 521.17
    n-dodecane 66.35
    diethylene glycol 682.98
    diisopropyl ether 164.11
    tert-amyl alcohol 425.73
    acetylacetone 247.41
    n-hexadecane 68.4
    acetophenone 198.7
    methyl propionate 250.99
    isopentyl acetate 231.92
    trichloroethylene 511.07
    n-nonanol 327.13
    cyclohexanol 520.44
    benzyl alcohol 249.39
    2-ethylhexanol 288.88
    isooctanol 217.78
    dipropyl ether 359.45
    1,2-dichlorobenzene 188.01
    ethyl lactate 186.59
    propylene carbonate 296.17
    n-methylformamide 646.54
    2-pentanol 380.8
    n-pentane 272.76
    1-propoxy-2-propanol 579.25
    1-methoxy-2-propyl acetate 284.1
    2-(2-methoxypropoxy) propanol 352.88
    mesitylene 103.45
    ε-caprolactone 417.52
    p-cymene 104.45
    epichlorohydrin 550.48
    1,1,1-trichloroethane 301.22
    2-aminoethanol 744.67
    morpholine-4-carbaldehyde 726.35
    sulfolane 482.88
    2,2,4-trimethylpentane 71.01
    2-methyltetrahydrofuran 639.42
    n-hexyl acetate 318.15
    isooctane 57.59
    2-(2-butoxyethoxy)ethanol 539.54
    sec-butyl acetate 153.62
    tert-butyl acetate 198.97
    decalin 102.67
    glycerin 668.83
    diglyme 787.45
    acrylic acid 440.3
    isopropyl myristate 149.18
    n-butyric acid 492.31
    acetyl acetate 179.4
    di(2-ethylhexyl) phthalate 145.34
    ethyl propionate 198.8
    nitromethane 596.5
    1,2-diethoxyethane 383.71
    benzonitrile 229.83
    trioctyl phosphate 129.1
    1-bromopropane 346.82
    gamma-valerolactone 711.3
    n-decanol 247.13
    triethyl phosphate 127.68
    4-methyl-2-pentanol 210.96
    propionitrile 290.7
    vinylene carbonate 302.96
    1,1,2-trichlorotrifluoroethane 559.06
    DMS 173.64
    cumene 92.28
    2-octanol 226.8
    2-hexanone 254.74
    octyl acetate 208.22
    limonene 155.13
    1,2-dimethoxyethane 902.63
    ethyl orthosilicate 145.93
    tributyl phosphate 137.58
    diacetone alcohol 265.71
    N,N-dimethylaniline 197.73
    acrylonitrile 306.57
    aniline 314.15
    1,3-propanediol 765.14
    bromobenzene 199.84
    dibromomethane 488.73
    1,1,2,2-tetrachloroethane 565.08
    2-methyl-cyclohexyl acetate 198.2
    tetrabutyl urea 181.23
    diisobutyl methanol 154.08
    2-phenylethanol 299.39
    styrene 170.55
    dioctyl adipate 180.73
    dimethyl sulfate 163.37
    ethyl butyrate 209.53
    methyl lactate 243.36
    butyl lactate 235.77
    diethyl carbonate 160.08
    propanediol butyl ether 470.02
    triethyl orthoformate 220.23
    p-tert-butyltoluene 110.41
    methyl 4-tert-butylbenzoate 213.1
    morpholine 1198.0
    tert-butylamine 447.42
    n-dodecanol 193.2
    dimethoxymethane 574.27
    ethylene carbonate 288.5
    cyrene 253.6
    2-ethoxyethyl acetate 253.94
    2-ethylhexyl acetate 207.5
    1,2,4-trichlorobenzene 231.2
    4-methylpyridine 368.7
    dibutyl ether 286.86
    2,6-dimethyl-4-heptanol 154.08
    DEF 340.32
    dimethyl isosorbide 446.46
    tetrachloroethylene 442.66
    eugenol 265.71
    triacetin 238.17
    span 80 400.94
    1,4-butanediol 366.8
    1,1-dichloroethane 355.81
    2-methyl-1-pentanol 282.38
    methyl formate 440.21
    2-methyl-1-butanol 357.87
    n-decane 110.92
    butyronitrile 313.28
    3,7-dimethyl-1-octanol 253.47
    1-chlorooctane 202.11
    1-chlorotetradecane 101.12
    n-nonane 112.96
    undecane 83.09
    tert-butylcyclohexane 84.84
    cyclooctane 161.66
    cyclopentanol 603.28
    tetrahydropyran 923.06
    tert-amyl methyl ether 279.53
    2,5,8-trioxanonane 562.56
    1-hexene 350.4
    2-isopropoxyethanol 380.79
    2,2,2-trifluoroethanol 317.77
    methyl butyrate 256.09

    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