Bis(trimethylsilyl)lactate

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  • Identifiers

    CAS number
    17596-96-2

    Molecular formula
    C9H22O3Si2

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

    Safety labels

  • Odor profile

    Fragrance
    Fruity 40.05%
    Mint 31.12%
    Odorless 26.02%
    Woody 24.62%
    Floral 22.76%
    Fresh 21.55%
    Ethereal 20.9%
    Herbal 20.65%
    Fermented 20.64%
    Green 20.39%

     

    Flavor
    Fruity 46.23%
    Green 34.19%
    Sweet 30.95%
    Tropical 28.31%
    Citrus 28.13%
    Herbal 25.79%
    Bitter 24.78%
    Mild 22.15%
    Grape skin 21.48%
    Pungent 21.28%

     

    Odor impact est.
    Medium

  • Properties

    pKa est.
    10.58 (weak base)

    Molecular weight
    234.44 g/mol

    Flash point

    • 77.56 ˚C est.

  • Synonyms

    • 17596-96-2
    • Bis(trimethylsilyl)lactate
    • Propionic acid, 2-(trimethylsiloxy)-, trimethylsilyl ester
    • Propanoic acid, 2-[(trimethylsilyl)oxy]-, trimethylsilyl ester
    • Lactic acid, di-TMS
    • Lactic acid, bis-TMS
    • Lactic acid, (2TMS)
    • Lactic acid, O,O-TMS
    • Trimethylsilyl 2-[(trimethylsilyl)oxy]propanoate
    • Lactic Acid, 2TMS derivative
    • Lactic acid, bis(trimethylsilyl)oxy-, ester
    • Trimethylsilyl 2-((trimethylsilyl)oxy)propanoate
    • 2-Trimethylsilyloxypropionic acid,trimethylsilyl ester
    • Propanoic acid, 2-((trimethylsilyl)oxy)-, trimethylsilyl ester
    • RefChem:329933
    • HXRGKEOWDNVHPA-UHFFFAOYSA-N
    • trimethylsilyl 2-trimethylsilyloxypropanoate
    • TRIMETHYLSILYL TRIMETHYLSILOXY LACTATE
    • o,o-Bis(trimethylsilyl)lactate
    • DTXSID201021853
    • 2-[(trimethylsilyl)oxy]propanoic acid trimethylsilyl ester
    • 17596-96-2

  • Applications

    Bis(trimethylsilyl)lactate, CAS 17596-96-2, is the silyl-protected lactate derivative primarily used as a protective group and synthetic intermediate in organic chemistry. In industrial contexts, it serves as a building block for chiral lactate derivatives used in pharmaceutical and agrochemical synthesis, enabling selective transformations on the lactic framework prior to deprotection. It can also function as a precursor to specialty lactate-derived polymers or coatings, where protected hydroxyl and carboxyl functionalities are required during formulation. Additionally, it is employed as a protected-group source in multi-step syntheses of complex compounds, with use governed by local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1136.51
    methanol 1474.77
    isopropanol 735.31
    water 20.83
    ethyl acetate 296.43
    n-propanol 867.63
    acetone 528.16
    n-butanol 693.58
    acetonitrile 346.92
    DMF 803.83
    toluene 295.46
    isobutanol 522.25
    1,4-dioxane 906.01
    methyl acetate 363.98
    THF 1334.61
    2-butanone 432.48
    n-pentanol 545.19
    sec-butanol 636.41
    n-hexane 379.65
    ethylene glycol 346.28
    NMP 677.89
    cyclohexane 536.78
    DMSO 686.2
    n-butyl acetate 366.13
    n-octanol 402.04
    chloroform 921.96
    n-propyl acetate 274.45
    acetic acid 702.09
    dichloromethane 643.17
    cyclohexanone 629.42
    propylene glycol 407.75
    isopropyl acetate 235.27
    DMAc 630.57
    2-ethoxyethanol 630.76
    isopentanol 443.56
    n-heptane 260.23
    ethyl formate 342.13
    1,2-dichloroethane 466.79
    n-hexanol 689.63
    2-methoxyethanol 971.82
    isobutyl acetate 199.34
    tetrachloromethane 233.61
    n-pentyl acetate 295.51
    transcutol 875.8
    n-heptanol 363.31
    ethylbenzene 192.87
    MIBK 242.56
    2-propoxyethanol 840.53
    tert-butanol 548.16
    MTBE 431.29
    2-butoxyethanol 491.09
    propionic acid 462.16
    o-xylene 186.57
    formic acid 488.98
    diethyl ether 591.4
    m-xylene 190.0
    p-xylene 221.98
    chlorobenzene 299.62
    dimethyl carbonate 155.53
    n-octane 115.66
    formamide 441.31
    cyclopentanone 633.74
    2-pentanone 357.8
    anisole 274.69
    cyclopentyl methyl ether 544.03
    gamma-butyrolactone 615.19
    1-methoxy-2-propanol 640.69
    pyridine 556.05
    3-pentanone 289.54
    furfural 581.21
    n-dodecane 75.05
    diethylene glycol 593.31
    diisopropyl ether 203.12
    tert-amyl alcohol 482.86
    acetylacetone 285.22
    n-hexadecane 78.8
    acetophenone 234.65
    methyl propionate 276.31
    isopentyl acetate 316.57
    trichloroethylene 611.39
    n-nonanol 350.29
    cyclohexanol 646.8
    benzyl alcohol 265.3
    2-ethylhexanol 357.02
    isooctanol 260.6
    dipropyl ether 410.49
    1,2-dichlorobenzene 244.36
    ethyl lactate 184.81
    propylene carbonate 359.56
    n-methylformamide 534.51
    2-pentanol 440.39
    n-pentane 338.66
    1-propoxy-2-propanol 537.69
    1-methoxy-2-propyl acetate 316.3
    2-(2-methoxypropoxy) propanol 315.6
    mesitylene 140.07
    ε-caprolactone 534.81
    p-cymene 142.38
    epichlorohydrin 613.06
    1,1,1-trichloroethane 381.97
    2-aminoethanol 593.75
    morpholine-4-carbaldehyde 697.03
    sulfolane 591.66
    2,2,4-trimethylpentane 102.2
    2-methyltetrahydrofuran 780.99
    n-hexyl acetate 412.27
    isooctane 80.48
    2-(2-butoxyethoxy)ethanol 472.03
    sec-butyl acetate 192.88
    tert-butyl acetate 241.8
    decalin 143.21
    glycerin 480.79
    diglyme 691.22
    acrylic acid 395.72
    isopropyl myristate 173.2
    n-butyric acid 518.29
    acetyl acetate 208.84
    di(2-ethylhexyl) phthalate 163.96
    ethyl propionate 228.07
    nitromethane 575.04
    1,2-diethoxyethane 382.32
    benzonitrile 286.17
    trioctyl phosphate 147.56
    1-bromopropane 486.17
    gamma-valerolactone 824.82
    n-decanol 255.32
    triethyl phosphate 138.67
    4-methyl-2-pentanol 251.91
    propionitrile 344.69
    vinylene carbonate 357.18
    1,1,2-trichlorotrifluoroethane 512.82
    DMS 212.47
    cumene 128.68
    2-octanol 280.75
    2-hexanone 321.38
    octyl acetate 235.51
    limonene 216.98
    1,2-dimethoxyethane 823.19
    ethyl orthosilicate 156.94
    tributyl phosphate 153.2
    diacetone alcohol 274.65
    N,N-dimethylaniline 226.0
    acrylonitrile 333.5
    aniline 332.98
    1,3-propanediol 651.86
    bromobenzene 280.54
    dibromomethane 590.24
    1,1,2,2-tetrachloroethane 639.67
    2-methyl-cyclohexyl acetate 249.51
    tetrabutyl urea 207.71
    diisobutyl methanol 188.86
    2-phenylethanol 316.94
    styrene 219.77
    dioctyl adipate 199.78
    dimethyl sulfate 177.74
    ethyl butyrate 238.14
    methyl lactate 216.92
    butyl lactate 269.58
    diethyl carbonate 172.59
    propanediol butyl ether 456.69
    triethyl orthoformate 228.58
    p-tert-butyltoluene 144.98
    methyl 4-tert-butylbenzoate 246.47
    morpholine 1119.1
    tert-butylamine 465.11
    n-dodecanol 195.56
    dimethoxymethane 562.02
    ethylene carbonate 339.56
    cyrene 254.38
    2-ethoxyethyl acetate 296.37
    2-ethylhexyl acetate 289.99
    1,2,4-trichlorobenzene 282.52
    4-methylpyridine 473.83
    dibutyl ether 327.22
    2,6-dimethyl-4-heptanol 188.86
    DEF 395.66
    dimethyl isosorbide 432.47
    tetrachloroethylene 490.9
    eugenol 277.64
    triacetin 269.08
    span 80 366.32
    1,4-butanediol 333.27
    1,1-dichloroethane 434.43
    2-methyl-1-pentanol 366.12
    methyl formate 384.47
    2-methyl-1-butanol 458.38
    n-decane 128.2
    butyronitrile 392.65
    3,7-dimethyl-1-octanol 290.32
    1-chlorooctane 245.63
    1-chlorotetradecane 115.81
    n-nonane 134.26
    undecane 93.47
    tert-butylcyclohexane 120.42
    cyclooctane 199.33
    cyclopentanol 653.3
    tetrahydropyran 1070.69
    tert-amyl methyl ether 358.4
    2,5,8-trioxanonane 462.49
    1-hexene 493.22
    2-isopropoxyethanol 372.37
    2,2,2-trifluoroethanol 253.31
    methyl butyrate 297.95

    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