Trimethylsilyl 2-trimethylsilyloxybenzoate

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  • Identifiers

    CAS number
    3789-85-3

    Molecular formula
    C13H22O3Si2

    SMILES
    C[Si](C)(C)OC1=CC=CC=C1C(=O)O[Si](C)(C)C

    Safety labels

  • Odor profile

    Fragrance
    Floral 46.96%
    Herbal 45.8%
    Fruity 41.03%
    Green 36.7%
    Mint 33.9%
    Woody 33.13%
    Fresh 29.02%
    Sweet 27.6%
    Balsamic 26.67%
    Camphoreous 26.08%

     

    Flavor
    Bitter 51.18%
    Herbal 39.33%
    Sweet 36.3%
    Fruity 35.09%
    Citrus 26.69%
    Camphor 25.02%
    Bergamot 23.6%
    Green 23.11%
    Floral 23.02%
    Lavender 22.46%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    8.44 (weak base)

    Molecular weight
    282.48 g/mol

    Flash point

    • 115.17 ˚C est.

  • Synonyms

    • 3789-85-3
    • trimethylsilyl 2-trimethylsilyloxybenzoate
    • DTXSID801021356
    • RefChem:1100471
    • DTXCID001506398
    • Benzoic acid, 2-[(trimethylsilyl)oxy]-, trimethylsilyl ester
    • trimethylsilyl trimethylsiloxy salicylate
    • Benzoic acid, o-(trimethylsiloxy)-, trimethylsilyl ester
    • Salicylic acid (2TMS)
    • Salicylic acid, di-TMS
    • Salicylic acid, bis-TMS
    • Trimethylsilyl 2-[(trimethylsilyl)oxy]benzoate
    • SCHEMBL7608797
    • SCHEMBL30420964
    • Salicylic acid, 2TMS derivative
    • BENZOIC ACID,2-TRIMETHYLSILOXY,TRIMETHYLSILYL ESTER
    • Benzoic acid, 2-hydroxy, di-TMS
    • trimethylsilyl 2-trimethylsiloxybenzoate
    • 2-Hydroxybenzoic acid, di(trimethylsilyl) deriv.
    • Bis(trimethylsilyl) derivative of Salicylic acid
    • Trimethylsilyl 2-[(trimethylsilyl)oxy]benzoate #
    • Q63392143
    • 2-TRIMETHYLSILOXYBENZOIC ACID TRIMETHYLSILYL ESTER
    • InChI=1/C13H22O3Si2/c1-17(2,3)15-12-10-8-7-9-11(12)13(14)16-18(4,5)6/h7-10H,1-6H
    • 3789-85-3

  • Applications

    This compound, Trimethylsilyl 2-trimethylsilyloxybenzoate (CAS 3789-85-3), is commonly used as a protected salicylate building block in organic synthesis, with both trimethylsilyl-protected sites enabling chemoselective, multi-step sequences by masking reactive functionalities until deprotection. It serves as an intermediate in pharmaceutical and agrochemical development, where the salicylate core can be revealed after suitable processing. It can function as a precursor for salicylate-containing monomers or linkers in polymer and coating chemistries, expanding options for functional materials. In method development and library synthesis, it provides a flexible masked difunctional scaffold that supports selective transformations without premature side reactions. Overall, its role is as a protecting-group-compatible building block and synthetic intermediate across diverse industrial chemistry contexts, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 329.47
    methanol 317.78
    isopropanol 281.88
    water 3.58
    ethyl acetate 358.16
    n-propanol 284.71
    acetone 733.21
    n-butanol 263.66
    acetonitrile 259.17
    DMF 1092.38
    toluene 201.37
    isobutanol 218.66
    1,4-dioxane 583.39
    methyl acetate 399.9
    THF 1682.51
    2-butanone 499.77
    n-pentanol 195.51
    sec-butanol 245.75
    n-hexane 80.96
    ethylene glycol 119.8
    NMP 1351.1
    cyclohexane 128.48
    DMSO 902.32
    n-butyl acetate 340.15
    n-octanol 202.8
    chloroform 886.76
    n-propyl acetate 273.74
    acetic acid 462.54
    dichloromethane 673.05
    cyclohexanone 867.17
    propylene glycol 229.0
    isopropyl acetate 292.7
    DMAc 877.69
    2-ethoxyethanol 276.17
    isopentanol 225.79
    n-heptane 71.57
    ethyl formate 255.47
    1,2-dichloroethane 505.0
    n-hexanol 274.86
    2-methoxyethanol 483.19
    isobutyl acetate 222.49
    tetrachloromethane 100.95
    n-pentyl acetate 280.9
    transcutol 627.72
    n-heptanol 179.32
    ethylbenzene 108.53
    MIBK 332.35
    2-propoxyethanol 480.93
    tert-butanol 299.74
    MTBE 296.2
    2-butoxyethanol 303.1
    propionic acid 364.15
    o-xylene 130.26
    formic acid 166.39
    diethyl ether 297.3
    m-xylene 160.43
    p-xylene 151.63
    chlorobenzene 311.82
    dimethyl carbonate 289.19
    n-octane 37.11
    formamide 214.16
    cyclopentanone 1322.9
    2-pentanone 465.25
    anisole 242.71
    cyclopentyl methyl ether 654.61
    gamma-butyrolactone 1290.37
    1-methoxy-2-propanol 470.77
    pyridine 505.87
    3-pentanone 358.37
    furfural 783.21
    n-dodecane 32.06
    diethylene glycol 315.67
    diisopropyl ether 136.96
    tert-amyl alcohol 259.38
    acetylacetone 600.19
    n-hexadecane 35.81
    acetophenone 269.17
    methyl propionate 399.73
    isopentyl acetate 303.9
    trichloroethylene 937.93
    n-nonanol 181.36
    cyclohexanol 337.86
    benzyl alcohol 198.77
    2-ethylhexanol 182.53
    isooctanol 147.15
    dipropyl ether 254.29
    1,2-dichlorobenzene 279.61
    ethyl lactate 195.52
    propylene carbonate 714.09
    n-methylformamide 394.9
    2-pentanol 212.36
    n-pentane 73.89
    1-propoxy-2-propanol 364.02
    1-methoxy-2-propyl acetate 390.41
    2-(2-methoxypropoxy) propanol 282.88
    mesitylene 113.1
    ε-caprolactone 676.14
    p-cymene 95.57
    epichlorohydrin 931.28
    1,1,1-trichloroethane 432.96
    2-aminoethanol 215.31
    morpholine-4-carbaldehyde 861.01
    sulfolane 1472.28
    2,2,4-trimethylpentane 38.14
    2-methyltetrahydrofuran 801.06
    n-hexyl acetate 387.16
    isooctane 34.73
    2-(2-butoxyethoxy)ethanol 367.36
    sec-butyl acetate 198.98
    tert-butyl acetate 344.59
    decalin 55.9
    glycerin 291.48
    diglyme 584.26
    acrylic acid 351.2
    isopropyl myristate 164.97
    n-butyric acid 418.47
    acetyl acetate 279.33
    di(2-ethylhexyl) phthalate 169.82
    ethyl propionate 255.77
    nitromethane 688.06
    1,2-diethoxyethane 292.62
    benzonitrile 273.18
    trioctyl phosphate 139.16
    1-bromopropane 312.14
    gamma-valerolactone 1223.09
    n-decanol 136.6
    triethyl phosphate 145.97
    4-methyl-2-pentanol 151.47
    propionitrile 238.52
    vinylene carbonate 548.84
    1,1,2-trichlorotrifluoroethane 622.21
    DMS 346.1
    cumene 85.05
    2-octanol 147.21
    2-hexanone 315.06
    octyl acetate 216.2
    limonene 158.18
    1,2-dimethoxyethane 506.37
    ethyl orthosilicate 140.32
    tributyl phosphate 156.91
    diacetone alcohol 390.26
    N,N-dimethylaniline 195.69
    acrylonitrile 303.05
    aniline 245.06
    1,3-propanediol 258.86
    bromobenzene 302.02
    dibromomethane 500.76
    1,1,2,2-tetrachloroethane 835.82
    2-methyl-cyclohexyl acetate 253.27
    tetrabutyl urea 235.33
    diisobutyl methanol 122.81
    2-phenylethanol 230.8
    styrene 132.63
    dioctyl adipate 236.89
    dimethyl sulfate 450.68
    ethyl butyrate 253.52
    methyl lactate 300.03
    butyl lactate 259.71
    diethyl carbonate 180.93
    propanediol butyl ether 334.46
    triethyl orthoformate 205.21
    p-tert-butyltoluene 103.45
    methyl 4-tert-butylbenzoate 294.07
    morpholine 700.46
    tert-butylamine 204.49
    n-dodecanol 110.55
    dimethoxymethane 621.64
    ethylene carbonate 487.23
    cyrene 351.87
    2-ethoxyethyl acetate 325.04
    2-ethylhexyl acetate 256.77
    1,2,4-trichlorobenzene 363.15
    4-methylpyridine 468.12
    dibutyl ether 215.19
    2,6-dimethyl-4-heptanol 122.81
    DEF 463.88
    dimethyl isosorbide 529.44
    tetrachloroethylene 454.95
    eugenol 266.16
    triacetin 358.15
    span 80 328.98
    1,4-butanediol 123.07
    1,1-dichloroethane 486.3
    2-methyl-1-pentanol 163.41
    methyl formate 354.72
    2-methyl-1-butanol 214.54
    n-decane 52.48
    butyronitrile 256.11
    3,7-dimethyl-1-octanol 170.03
    1-chlorooctane 157.28
    1-chlorotetradecane 74.31
    n-nonane 51.95
    undecane 39.92
    tert-butylcyclohexane 52.81
    cyclooctane 54.09
    cyclopentanol 457.59
    tetrahydropyran 684.97
    tert-amyl methyl ether 253.39
    2,5,8-trioxanonane 423.05
    1-hexene 167.88
    2-isopropoxyethanol 214.31
    2,2,2-trifluoroethanol 216.57
    methyl butyrate 327.01

    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