Benzyl bromoacetate

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  • Identifiers

    CAS number
    5437-45-6

    Molecular formula
    C9H9BrO2

    SMILES
    C1=CC=C(C=C1)COC(=O)CBr

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 73.84%
    Sweet 59.09%
    Honey 41.87%
    Floral 41.76%
    Caramellic 40.64%
    Balsamic 35.91%
    Fatty 31.61%
    Winey 31.6%
    Rose 28.55%
    Pineapple 25.36%

     

    Flavor
    Fruity 78.16%
    Sweet 69.89%
    Floral 46.67%
    Grape 44.65%
    Balsam 36.59%
    Strawberry 35.17%
    Berry 34.37%
    Pineapple 31.87%
    Powdery 31.87%
    Wine 30.38%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    7.14 (neutral)

    Molecular weight
    229.07 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    280°C

    Flash point

    • 117.86 ˚C est.

  • Synonyms

    • Benzyl 2-bromoacetate
    • Benzyl bromoacetate
    • 5437-45-6
    • Bromoacetic acid benzyl ester
    • Acetic acid, bromo-, phenylmethyl ester
    • Merbac 35
    • DTXSID4040343
    • 64U2RK18D3
    • NSC-16114
    • NSC-23980
    • DTXCID2020343
    • RefChem:1079468
    • 226-611-4
    • MFCD00000190
    • 2-Bromoacetic Acid Phenylmethyl Ester
    • Acetic acid, bromo-, benzyl ester
    • benzyl-2-bromoacetate
    • phenylmethyl 2-bromoacetate
    • Caswell No. 082A
    • Benzyl2-bromoacetate
    • phenylmethyl bromoacetate
    • EINECS 226-611-4
    • EPA Pesticide Chemical Code 008710
    • BRN 0973658
    • UNII-64U2RK18D3
    • AI3-18917
    • 2-Bromoacetic acid benzyl ester
    • benzyl bromacetate
    • benzyl bromo-acetate
    • benzyl-2-bromacetate
    • benzyl-2-bromoacteate
    • benzyl 2-bromo-acetate
    • Benzyl bromoacetate, 96%
    • bromoacetic acid-benzylester
    • 4-06-00-02265 (Beilstein Handbook Reference)
    • SCHEMBL112615
    • bromo-acetic acid benzyl ester
    • Bromoacetic acid, benzyl ester
    • CHEMBL3184596
    • JHVLLYQQQYIWKX-UHFFFAOYSA-
    • bromoacetic acid. phenylmethyl ester
    • NSC16114
    • NSC23980
    • STR04959
    • alpha-bromo-acetic acid benzyl ester
    • Tox21_302092
    • NSC 16114
    • NSC 23980
    • SBB006752
    • STL299665
    • AKOS015836017
    • CS-W010391
    • FB02468
    • PB43021
    • NCGC00255660-01
    • SY002918
    • CAS-5437-45-6
    • DB-020655
    • NS00021204
    • Benzyl bromoacetate, purum, >=97.0% (GC)
    • EN300-72660
    • P19617
    • F319046
    • Q27263791
    • F2190-0284
    • InChI=1/C9H9BrO2/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5H,6-7H2
    • 5437-45-6

  • Applications

    Benzyl bromoacetate (CAS 5437-45-6) is primarily used as a versatile intermediate in organic synthesis, providing a benzyl ester framework with a bromomethyl handle that enables subsequent functionalization. It is commonly employed to introduce bromomethyl functionality for nucleophilic substitution, facilitating the preparation of benzyl-protected amines, alcohols, and carboxylate derivatives. In pharmaceutical and agrochemical synthesis, it serves as a building block for more complex intermediates and as part of protecting-group strategies in multi-step routes. In polymer chemistry and coatings, it can function as a reactive building block to graft benzyl-protected units or to install bromomethyl sites for post-polymerization modification. In fragrance chemistry, it may be used as a precursor for synthesizing benzyl-containing fragrance compounds. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 55.63
    methanol 48.97
    isopropanol 32.02
    water 0.22
    ethyl acetate 74.96
    n-propanol 42.66
    acetone 137.03
    n-butanol 40.77
    acetonitrile 67.6
    DMF 121.35
    toluene 59.59
    isobutanol 31.07
    1,4-dioxane 178.82
    methyl acetate 92.48
    THF 229.8
    2-butanone 102.99
    n-pentanol 48.58
    sec-butanol 36.07
    n-hexane 4.11
    ethylene glycol 18.59
    NMP 141.92
    cyclohexane 8.27
    DMSO 195.49
    n-butyl acetate 78.16
    n-octanol 23.07
    chloroform 289.65
    n-propyl acetate 77.78
    acetic acid 89.36
    dichloromethane 273.18
    cyclohexanone 129.04
    propylene glycol 16.86
    isopropyl acetate 49.95
    DMAc 176.33
    2-ethoxyethanol 101.97
    isopentanol 43.06
    n-heptane 7.23
    ethyl formate 53.26
    1,2-dichloroethane 172.54
    n-hexanol 44.01
    2-methoxyethanol 105.35
    isobutyl acetate 54.8
    tetrachloromethane 24.4
    n-pentyl acetate 46.28
    transcutol 437.14
    n-heptanol 27.24
    ethylbenzene 35.65
    MIBK 59.68
    2-propoxyethanol 92.99
    tert-butanol 47.18
    MTBE 50.5
    2-butoxyethanol 69.53
    propionic acid 46.71
    o-xylene 44.3
    formic acid 35.21
    diethyl ether 63.77
    m-xylene 41.69
    p-xylene 44.14
    chlorobenzene 82.77
    dimethyl carbonate 43.08
    n-octane 2.56
    formamide 62.8
    cyclopentanone 155.49
    2-pentanone 74.42
    anisole 91.22
    cyclopentyl methyl ether 86.17
    gamma-butyrolactone 160.39
    1-methoxy-2-propanol 71.33
    pyridine 169.53
    3-pentanone 69.86
    furfural 187.36
    n-dodecane 2.71
    diethylene glycol 85.95
    diisopropyl ether 22.5
    tert-amyl alcohol 45.95
    acetylacetone 111.69
    n-hexadecane 3.11
    acetophenone 96.79
    methyl propionate 64.77
    isopentyl acetate 71.04
    trichloroethylene 343.52
    n-nonanol 23.36
    cyclohexanol 45.79
    benzyl alcohol 75.65
    2-ethylhexanol 37.48
    isooctanol 26.1
    dipropyl ether 48.24
    1,2-dichlorobenzene 79.17
    ethyl lactate 41.66
    propylene carbonate 92.93
    n-methylformamide 55.77
    2-pentanol 30.73
    n-pentane 3.9
    1-propoxy-2-propanol 69.95
    1-methoxy-2-propyl acetate 86.45
    2-(2-methoxypropoxy) propanol 84.61
    mesitylene 25.54
    ε-caprolactone 111.09
    p-cymene 28.64
    epichlorohydrin 233.8
    1,1,1-trichloroethane 102.35
    2-aminoethanol 31.44
    morpholine-4-carbaldehyde 178.17
    sulfolane 181.35
    2,2,4-trimethylpentane 4.69
    2-methyltetrahydrofuran 124.62
    n-hexyl acetate 49.79
    isooctane 3.25
    2-(2-butoxyethoxy)ethanol 108.11
    sec-butyl acetate 55.46
    tert-butyl acetate 60.45
    decalin 7.49
    glycerin 32.71
    diglyme 222.75
    acrylic acid 54.47
    isopropyl myristate 28.79
    n-butyric acid 53.86
    acetyl acetate 66.27
    di(2-ethylhexyl) phthalate 35.3
    ethyl propionate 58.45
    nitromethane 152.61
    1,2-diethoxyethane 118.19
    benzonitrile 86.17
    trioctyl phosphate 22.02
    1-bromopropane 66.12
    gamma-valerolactone 185.63
    n-decanol 18.96
    triethyl phosphate 38.96
    4-methyl-2-pentanol 25.07
    propionitrile 49.91
    vinylene carbonate 91.61
    1,1,2-trichlorotrifluoroethane 162.44
    DMS 66.17
    cumene 26.91
    2-octanol 18.25
    2-hexanone 81.04
    octyl acetate 33.26
    limonene 38.85
    1,2-dimethoxyethane 176.93
    ethyl orthosilicate 37.97
    tributyl phosphate 27.55
    diacetone alcohol 76.42
    N,N-dimethylaniline 67.41
    acrylonitrile 68.18
    aniline 72.8
    1,3-propanediol 42.43
    bromobenzene 82.59
    dibromomethane 162.96
    1,1,2,2-tetrachloroethane 241.49
    2-methyl-cyclohexyl acetate 59.72
    tetrabutyl urea 41.7
    diisobutyl methanol 26.0
    2-phenylethanol 65.14
    styrene 47.97
    dioctyl adipate 50.54
    dimethyl sulfate 75.26
    ethyl butyrate 65.58
    methyl lactate 39.91
    butyl lactate 44.77
    diethyl carbonate 50.76
    propanediol butyl ether 61.39
    triethyl orthoformate 51.39
    p-tert-butyltoluene 26.3
    methyl 4-tert-butylbenzoate 67.82
    morpholine 165.88
    tert-butylamine 30.99
    n-dodecanol 15.82
    dimethoxymethane 102.14
    ethylene carbonate 71.6
    cyrene 97.6
    2-ethoxyethyl acetate 81.72
    2-ethylhexyl acetate 61.31
    1,2,4-trichlorobenzene 96.65
    4-methylpyridine 127.22
    dibutyl ether 35.71
    2,6-dimethyl-4-heptanol 26.0
    DEF 88.79
    dimethyl isosorbide 137.34
    tetrachloroethylene 156.24
    eugenol 74.65
    triacetin 76.82
    span 80 65.28
    1,4-butanediol 27.06
    1,1-dichloroethane 111.2
    2-methyl-1-pentanol 49.74
    methyl formate 55.54
    2-methyl-1-butanol 39.3
    n-decane 3.77
    butyronitrile 49.85
    3,7-dimethyl-1-octanol 29.36
    1-chlorooctane 17.81
    1-chlorotetradecane 9.43
    n-nonane 3.2
    undecane 3.1
    tert-butylcyclohexane 6.57
    cyclooctane 3.7
    cyclopentanol 47.57
    tetrahydropyran 125.45
    tert-amyl methyl ether 49.19
    2,5,8-trioxanonane 160.49
    1-hexene 20.81
    2-isopropoxyethanol 81.28
    2,2,2-trifluoroethanol 37.88
    methyl butyrate 77.08

    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