Bromoacetyl bromide

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  • Identifiers

    CAS number
    598-21-0

    Molecular formula
    C2H2Br2O

    SMILES
    C(C(=O)Br)Br

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Odorless 57.52%
    Meaty 29.51%
    Savory 26.27%
    Roasted 22.28%
    Sweet 22.03%
    Fishy 21.77%
    Cooked 19.95%
    Fatty 19.6%
    Sulfurous 18.84%
    Buttery 18.72%

     

    Flavor
    Odorless 46.65%
    Roasted 26.59%
    Sulfury 25.12%
    Cooked 24.93%
    Mild 23.61%
    Sulfurous 21.81%
    Mousy 20.52%
    Bland 20.2%
    Taco 19.53%
    Roasted peanuts 19.5%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    4.85 (weak acid)

    Molecular weight
    201.84 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point

    • 298 °F at 760 mmHg (USCG, 1999)

    Flash point

    • 57.68 ˚C est.

  • Synonyms

    • Bromoacetyl bromide
    • 598-21-0
    • 2-Bromoacetyl bromide
    • ACETYL BROMIDE, BROMO-
    • Acetyl bromide, 2-bromo-
    • bromoacetylbromide
    • bromo acetyl bromide
    • CCRIS 9090
    • EINECS 209-923-5
    • UN2513
    • alpha-bromoacetyl bromide
    • MFCD00000115
    • DTXSID1060506
    • bromoacetic acid bromide
    • C2H2Br2O
    • bromacetylbromide
    • bromacetyl bromide
    • bromoactyl bromide
    • bromo acetylbromide
    • bromo-acetylbromide
    • bromoacetyl-bromide
    • Bromoacetic bromide
    • 2-bromoacetylbromide
    • 2bromoacetyl bromide
    • Bromo-acetyl bromide
    • a-bromo-acetylbromide
    • a-Bromoacetyl bromide
    • Acetyl bromide, bromo
    • 2-bromo-acetyl bromide
    • alphaBromoacetyl bromide
    • Acetyl bromide, 2bromo
    • BROMOETHANOYL BROMIDE
    • SCHEMBL34263
    • alpha-bromoacetic acid bromide
    • MONOBROMOACETYL BROMIDE
    • Bromoacetyl bromide, >=98%
    • GV64Q4VP87
    • DTXCID7042699
    • LSTRKXWIZZZYAS-UHFFFAOYSA-
    • BCP28220
    • BBL027286
    • STL146513
    • AKOS000121172
    • FB31500
    • UN 2513
    • BP-31082
    • VS-08519
    • DB-072701
    • B0539
    • Bromoacetyl bromide [UN2513] [Corrosive]
    • NS00043338
    • Bromoacetyl bromide, purum, >=98.0% (AT)
    • EN300-25769
    • E78899
    • InChI=1/C2H2Br2O/c3-1-2(4)5/h1H2
    • A832485
    • F0001-1567
    • 209-923-5

  • Applications

    Bromoacetyl bromide (CAS 598-21-0) is a highly reactive acylating agent and a versatile building block in organic synthesis. In pharmaceutical and medicinal chemistry, it is used to install the alpha-bromoacetyl motif onto amines and other nucleophiles, yielding N-(bromoacetyl) derivatives that can be elaborated into amides, heterocycles, or other pharmacophores. It also serves to generate alpha-bromo ketone building blocks via subsequent transformations, enabling routes to diverse drug leads. In bioconjugation contexts, the reactive bromoacetyl group can be employed to label or conjugate to thiol groups (e.g., cysteine residues) on peptides or proteins. In polymer and materials science, it functions as a functional linker to introduce reactive sites for coatings, adhesives, and surface modification. Handling requires appropriate safety measures and compliance with local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 83.46
    methanol 95.5
    isopropanol 75.15
    water 12.94
    ethyl acetate 131.91
    n-propanol 81.02
    acetone 275.43
    n-butanol 75.62
    acetonitrile 189.36
    DMF 420.44
    toluene 120.93
    isobutanol 68.16
    1,4-dioxane 319.02
    methyl acetate 173.4
    THF 324.48
    2-butanone 192.42
    n-pentanol 79.02
    sec-butanol 80.39
    n-hexane 43.08
    ethylene glycol 55.53
    NMP 526.45
    cyclohexane 60.27
    DMSO 410.26
    n-butyl acetate 111.55
    n-octanol 84.19
    chloroform 207.68
    n-propyl acetate 124.42
    acetic acid 130.81
    dichloromethane 218.91
    cyclohexanone 239.44
    propylene glycol 37.76
    isopropyl acetate 100.58
    DMAc 481.76
    2-ethoxyethanol 178.21
    isopentanol 72.03
    n-heptane 49.29
    ethyl formate 105.08
    1,2-dichloroethane 167.18
    n-hexanol 76.91
    2-methoxyethanol 210.99
    isobutyl acetate 91.56
    tetrachloromethane 61.91
    n-pentyl acetate 97.22
    transcutol 481.24
    n-heptanol 57.05
    ethylbenzene 90.99
    MIBK 122.36
    2-propoxyethanol 164.84
    tert-butanol 99.69
    MTBE 124.05
    2-butoxyethanol 109.38
    propionic acid 81.11
    o-xylene 131.59
    formic acid 78.68
    diethyl ether 164.43
    m-xylene 106.1
    p-xylene 112.77
    chlorobenzene 118.92
    dimethyl carbonate 106.61
    n-octane 26.64
    formamide 140.09
    cyclopentanone 275.65
    2-pentanone 159.77
    anisole 183.87
    cyclopentyl methyl ether 199.18
    gamma-butyrolactone 250.48
    1-methoxy-2-propanol 156.59
    pyridine 224.45
    3-pentanone 170.41
    furfural 321.38
    n-dodecane 25.07
    diethylene glycol 162.93
    diisopropyl ether 81.63
    tert-amyl alcohol 96.48
    acetylacetone 230.42
    n-hexadecane 27.51
    acetophenone 199.0
    methyl propionate 139.6
    isopentyl acetate 100.01
    trichloroethylene 251.78
    n-nonanol 80.54
    cyclohexanol 108.93
    benzyl alcohol 122.56
    2-ethylhexanol 73.04
    isooctanol 54.45
    dipropyl ether 131.23
    1,2-dichlorobenzene 123.09
    ethyl lactate 81.77
    propylene carbonate 135.62
    n-methylformamide 167.45
    2-pentanol 67.48
    n-pentane 44.7
    1-propoxy-2-propanol 131.08
    1-methoxy-2-propyl acetate 137.68
    2-(2-methoxypropoxy) propanol 179.09
    mesitylene 83.44
    ε-caprolactone 182.88
    p-cymene 77.78
    epichlorohydrin 259.08
    1,1,1-trichloroethane 151.49
    2-aminoethanol 67.89
    morpholine-4-carbaldehyde 482.52
    sulfolane 330.7
    2,2,4-trimethylpentane 27.81
    2-methyltetrahydrofuran 227.47
    n-hexyl acetate 127.07
    isooctane 19.81
    2-(2-butoxyethoxy)ethanol 202.8
    sec-butyl acetate 95.91
    tert-butyl acetate 119.95
    decalin 43.72
    glycerin 69.96
    diglyme 365.0
    acrylic acid 93.66
    isopropyl myristate 86.82
    n-butyric acid 83.05
    acetyl acetate 118.96
    di(2-ethylhexyl) phthalate 79.58
    ethyl propionate 123.97
    nitromethane 298.23
    1,2-diethoxyethane 214.67
    benzonitrile 149.47
    trioctyl phosphate 58.84
    1-bromopropane 113.13
    gamma-valerolactone 347.93
    n-decanol 69.74
    triethyl phosphate 85.04
    4-methyl-2-pentanol 54.63
    propionitrile 116.69
    vinylene carbonate 135.81
    1,1,2-trichlorotrifluoroethane 214.31
    DMS 139.67
    cumene 77.28
    2-octanol 54.11
    2-hexanone 153.28
    octyl acetate 94.47
    limonene 105.37
    1,2-dimethoxyethane 382.01
    ethyl orthosilicate 85.22
    tributyl phosphate 73.17
    diacetone alcohol 136.47
    N,N-dimethylaniline 186.39
    acrylonitrile 139.73
    aniline 123.37
    1,3-propanediol 78.28
    bromobenzene 120.15
    dibromomethane 151.46
    1,1,2,2-tetrachloroethane 208.38
    2-methyl-cyclohexyl acetate 108.72
    tetrabutyl urea 121.31
    diisobutyl methanol 63.34
    2-phenylethanol 107.31
    styrene 107.77
    dioctyl adipate 117.26
    dimethyl sulfate 186.97
    ethyl butyrate 117.92
    methyl lactate 94.57
    butyl lactate 80.56
    diethyl carbonate 89.71
    propanediol butyl ether 116.9
    triethyl orthoformate 102.74
    p-tert-butyltoluene 74.24
    methyl 4-tert-butylbenzoate 147.57
    morpholine 280.4
    tert-butylamine 77.71
    n-dodecanol 62.74
    dimethoxymethane 270.02
    ethylene carbonate 111.86
    cyrene 200.98
    2-ethoxyethyl acetate 138.24
    2-ethylhexyl acetate 93.84
    1,2,4-trichlorobenzene 154.69
    4-methylpyridine 231.96
    dibutyl ether 122.39
    2,6-dimethyl-4-heptanol 63.34
    DEF 241.35
    dimethyl isosorbide 286.22
    tetrachloroethylene 150.61
    eugenol 158.82
    triacetin 169.87
    span 80 142.29
    1,4-butanediol 58.6
    1,1-dichloroethane 136.69
    2-methyl-1-pentanol 78.96
    methyl formate 160.19
    2-methyl-1-butanol 71.81
    n-decane 34.77
    butyronitrile 109.41
    3,7-dimethyl-1-octanol 86.9
    1-chlorooctane 72.02
    1-chlorotetradecane 45.51
    n-nonane 33.96
    undecane 28.64
    tert-butylcyclohexane 35.76
    cyclooctane 36.84
    cyclopentanol 116.89
    tetrahydropyran 202.79
    tert-amyl methyl ether 131.76
    2,5,8-trioxanonane 305.98
    1-hexene 77.2
    2-isopropoxyethanol 146.8
    2,2,2-trifluoroethanol 97.34
    methyl butyrate 140.31

    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