tert-Butyl bromoacetate

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  • Identifiers

    CAS number
    5292-43-3

    Molecular formula
    C6H11BrO2

    SMILES
    CC(C)(C)OC(=O)CBr

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 80.04%
    Sour 30.99%
    Cheesy 30.08%
    Fermented 28.33%
    Winey 24.41%
    Tropical 24.33%
    Ethereal 22.39%
    Herbal 22.31%
    Mint 21.42%
    Sweaty 21.28%

     

    Flavor
    Fruity 62.56%
    Tropical 35.44%
    Sweet 35.13%
    Green 31.53%
    Citrus 30.67%
    Herbal 30.32%
    Berry 27.16%
    Pineapple 25.93%
    Woody 25.06%
    Ripe 23.0%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    6.74 (neutral)

    Molecular weight
    195.05 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    179°C

    Flash point

    • 61.91 ˚C est.

  • Synonyms

    • tert-Butyl bromoacetate
    • 5292-43-3
    • tert-butyl 2-bromoacetate
    • t-Butyl bromoacetate
    • Bromoacetic Acid tert-Butyl Ester
    • Acetic acid, bromo-, 1,1-dimethylethyl ester
    • tert-Butylbromoacetate
    • MFCD00000188
    • t-butyl 2-bromoacetate
    • bromo-acetic acid tert-butyl ester
    • Acetic acid, bromo-, tert-butyl ester
    • LY42AF89SN
    • BrCH2C(O)OC(CH3)3
    • 1,1-dimethylethyl 2-bromoacetate
    • 1,1-Dimethylethyl monobromoacetate
    • Acetic acid, 2-bromo-, 1,1-dimethylethyl ester
    • 2-bromoacetic acid tert-butyl ester
    • Bromoacetic acid 1,1-dimethylethyl ester
    • tert-ButylBromoacetate-13C
    • t-butylbromoaceate
    • t-butylbromoacteate
    • t-Butylbromoacetate
    • EINECS 226-133-6
    • t-Butyl-bromoacetate
    • NSC 82470
    • tert butylbromoacetate
    • tertbutyl bromoacetate
    • tert-butyl bromacetate
    • tert butyl bromoacetate
    • tert-butyl-bromoacetate
    • tert.-butylbromoacetate
    • tert.butyl bromoacetate
    • Tert. butylbromoacetate
    • BrCH2CO2-t-Bu
    • t-butyl-2-bromoacetate
    • tert-butyl-bromo-acetate
    • tert-butyl2-bromoacetate
    • tert.-butyl bromoacetate
    • dimethylethyl bromoacetate
    • tertiarybutyl bromoacetate
    • t-buty alpha-bromoacetate
    • bromoacetate t-butyl ester
    • t-butyl alpha-bromoacetate
    • tert-Butyl-2-bromoacetate
    • tertiary butyl bromoacetate
    • T-BUTYL BROMOACTATE
    • Rosuvastatin Impurity 198
    • UNII-LY42AF89SN
    • tert-Butyl |A-bromoacetate
    • tert-butyl 2-bromo-acetate
    • NCIOpen2_001241
    • SCHEMBL38493
    • tert-butyl alpha-bromoacetate
    • 2-bromoacetate t-butyl ester
    • bromoacetic acid t-butyl ester
    • tert-butyl 2-bromanylethanoate
    • 1,1-dimethylethyl bromoacetate
    • tert-Butyl bromoacetate, 98%
    • bromoacetic acid tert-butylester
    • DTXSID2063763
    • SCHEMBL10968666
    • BNWCETAHAJSBFG-UHFFFAOYSA-
    • bromoacetic acid-tert-butyl ester
    • 2-bromoacetic acid-t butyl ester
    • bromoacetic acid tert.-butyl ester
    • bromo-acetic acid tert.-butyl ester
    • CS-D1664
    • NSC82470
    • STR02323
    • AB6559
    • NSC-82470
    • SBB070756
    • 2-bromoacetic acid tert.-butyl ester
    • AKOS009159099
    • FB02477
    • TERT-BUTYL .ALPHA.-BROMOACETATE
    • BP-20407
    • bromo-acetic acid 1,1-dimethylethyl ester
    • 2-bromoacetic acid 1,1-dimethylethyl ester
    • NS00032616
    • EN300-61309
    • tert-Butyl bromoacetate, purum, >=97.0% (GC)
    • A829312
    • F043685
    • F0001-1365
    • InChI=1/C6H11BrO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3
    • 5292-43-3

  • Applications

    tert-Butyl bromoacetate is a versatile alkylating reagent used in organic synthesis to introduce a protected bromoacetyl unit into nucleophiles such as amines and thiols, enabling formation of N- or C-substituted products bearing a tert-butyl ester. It serves as a key building block for constructing beta-substituted amino acid derivatives and peptidomimetics, and is widely employed in pharmaceutical and agrochemical syntheses. In addition, it is used as an intermediate for the synthesis of heterocycles and related functionalized compounds, and can be incorporated into polymer and materials chemistry workflows to install pendant ester functionality. Deprotection of the tert-butyl group provides access to the corresponding carboxylate after further transformations, with use subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 56.08
    methanol 67.57
    isopropanol 60.38
    water 3.66
    ethyl acetate 121.69
    n-propanol 60.24
    acetone 143.45
    n-butanol 59.35
    acetonitrile 86.89
    DMF 180.66
    toluene 113.62
    isobutanol 57.86
    1,4-dioxane 185.74
    methyl acetate 124.68
    THF 306.32
    2-butanone 125.64
    n-pentanol 52.09
    sec-butanol 69.0
    n-hexane 49.24
    ethylene glycol 33.52
    NMP 379.09
    cyclohexane 76.75
    DMSO 154.35
    n-butyl acetate 106.43
    n-octanol 88.6
    chloroform 386.0
    n-propyl acetate 85.83
    acetic acid 130.7
    dichloromethane 284.92
    cyclohexanone 219.97
    propylene glycol 46.48
    isopropyl acetate 91.79
    DMAc 248.28
    2-ethoxyethanol 83.64
    isopentanol 60.01
    n-heptane 41.59
    ethyl formate 73.6
    1,2-dichloroethane 164.86
    n-hexanol 87.58
    2-methoxyethanol 123.85
    isobutyl acetate 76.88
    tetrachloromethane 78.97
    n-pentyl acetate 92.36
    transcutol 236.98
    n-heptanol 57.11
    ethylbenzene 78.9
    MIBK 95.02
    2-propoxyethanol 140.36
    tert-butanol 93.94
    MTBE 102.28
    2-butoxyethanol 89.53
    propionic acid 97.3
    o-xylene 108.1
    formic acid 45.75
    diethyl ether 96.3
    m-xylene 104.85
    p-xylene 107.89
    chlorobenzene 144.5
    dimethyl carbonate 69.61
    n-octane 23.19
    formamide 47.77
    cyclopentanone 261.99
    2-pentanone 111.94
    anisole 131.78
    cyclopentyl methyl ether 201.86
    gamma-butyrolactone 277.77
    1-methoxy-2-propanol 119.13
    pyridine 167.62
    3-pentanone 118.29
    furfural 245.04
    n-dodecane 23.11
    diethylene glycol 114.88
    diisopropyl ether 59.34
    tert-amyl alcohol 91.49
    acetylacetone 162.21
    n-hexadecane 25.73
    acetophenone 134.6
    methyl propionate 117.54
    isopentyl acetate 105.21
    trichloroethylene 328.54
    n-nonanol 80.63
    cyclohexanol 121.5
    benzyl alcohol 90.09
    2-ethylhexanol 75.78
    isooctanol 53.16
    dipropyl ether 94.01
    1,2-dichlorobenzene 150.57
    ethyl lactate 67.95
    propylene carbonate 183.94
    n-methylformamide 80.88
    2-pentanol 61.28
    n-pentane 39.98
    1-propoxy-2-propanol 117.05
    1-methoxy-2-propyl acetate 128.03
    2-(2-methoxypropoxy) propanol 134.83
    mesitylene 79.35
    ε-caprolactone 200.18
    p-cymene 70.93
    epichlorohydrin 240.58
    1,1,1-trichloroethane 221.75
    2-aminoethanol 50.01
    morpholine-4-carbaldehyde 245.02
    sulfolane 344.84
    2,2,4-trimethylpentane 29.24
    2-methyltetrahydrofuran 229.65
    n-hexyl acetate 142.61
    isooctane 21.86
    2-(2-butoxyethoxy)ethanol 144.87
    sec-butyl acetate 75.09
    tert-butyl acetate 120.88
    decalin 46.38
    glycerin 71.54
    diglyme 205.29
    acrylic acid 105.97
    isopropyl myristate 76.53
    n-butyric acid 102.85
    acetyl acetate 112.35
    di(2-ethylhexyl) phthalate 82.89
    ethyl propionate 99.79
    nitromethane 167.43
    1,2-diethoxyethane 101.32
    benzonitrile 121.34
    trioctyl phosphate 62.16
    1-bromopropane 111.71
    gamma-valerolactone 262.23
    n-decanol 65.77
    triethyl phosphate 74.43
    4-methyl-2-pentanol 51.1
    propionitrile 79.25
    vinylene carbonate 159.85
    1,1,2-trichlorotrifluoroethane 212.61
    DMS 125.43
    cumene 68.55
    2-octanol 56.97
    2-hexanone 92.06
    octyl acetate 93.7
    limonene 99.19
    1,2-dimethoxyethane 156.12
    ethyl orthosilicate 71.6
    tributyl phosphate 69.82
    diacetone alcohol 127.19
    N,N-dimethylaniline 120.79
    acrylonitrile 99.83
    aniline 109.09
    1,3-propanediol 55.78
    bromobenzene 155.85
    dibromomethane 212.97
    1,1,2,2-tetrachloroethane 280.92
    2-methyl-cyclohexyl acetate 111.97
    tetrabutyl urea 95.81
    diisobutyl methanol 58.3
    2-phenylethanol 106.71
    styrene 89.45
    dioctyl adipate 105.57
    dimethyl sulfate 120.55
    ethyl butyrate 96.66
    methyl lactate 80.41
    butyl lactate 80.32
    diethyl carbonate 73.24
    propanediol butyl ether 107.14
    triethyl orthoformate 85.17
    p-tert-butyltoluene 76.48
    methyl 4-tert-butylbenzoate 144.81
    morpholine 180.95
    tert-butylamine 74.6
    n-dodecanol 55.54
    dimethoxymethane 138.69
    ethylene carbonate 125.96
    cyrene 152.5
    2-ethoxyethyl acetate 107.51
    2-ethylhexyl acetate 95.64
    1,2,4-trichlorobenzene 196.15
    4-methylpyridine 174.12
    dibutyl ether 85.95
    2,6-dimethyl-4-heptanol 58.3
    DEF 137.69
    dimethyl isosorbide 226.05
    tetrachloroethylene 182.07
    eugenol 133.69
    triacetin 147.69
    span 80 135.42
    1,4-butanediol 34.29
    1,1-dichloroethane 178.95
    2-methyl-1-pentanol 56.43
    methyl formate 82.21
    2-methyl-1-butanol 63.02
    n-decane 33.85
    butyronitrile 74.27
    3,7-dimethyl-1-octanol 87.24
    1-chlorooctane 81.95
    1-chlorotetradecane 45.07
    n-nonane 33.85
    undecane 27.1
    tert-butylcyclohexane 43.27
    cyclooctane 38.08
    cyclopentanol 128.13
    tetrahydropyran 181.94
    tert-amyl methyl ether 107.72
    2,5,8-trioxanonane 175.69
    1-hexene 74.31
    2-isopropoxyethanol 78.33
    2,2,2-trifluoroethanol 76.88
    methyl butyrate 106.62

    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