N-bromobutanimide

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  • Identifiers

    CAS number
    128-08-5

    Molecular formula
    C4H4BrNO2

    SMILES
    C1CC(=O)N(C1=O)Br

    Safety labels

    Oxidizer
    Oxidizer

    Corrosive
    Corrosive

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 53.6%
    Sweet 46.26%
    Caramellic 34.82%
    Burnt 32.64%
    Nutty 24.28%
    Ethereal 19.01%
    Popcorn 18.12%
    Roasted 16.05%
    Bitter 15.32%
    Spicy 15.26%

     

    Flavor
    Bitter 64.5%
    Odorless 28.55%
    Taco 20.08%
    Roasted 19.9%
    Nitrile 19.87%
    Bread crust 19.72%
    Very mild 19.6%
    Fenugreek 19.35%
    Roasted peanuts 19.26%
    Sweet-like 19.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    6.39 (neutral)

    Molecular weight
    177.98 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 173-175 °C (slight decomposition)
    • MP: 174 °C

    Boiling point

    • 338.9 °C at 101.325 kPa

    Flash point

    • 109.37 ˚C est.

    Solubility expt.

    • In water, 1.47 g/100 g water at 25 °C
    • Slightly soluble in water
    • Slightly soluble in ethyl acetate, diethyl ether; very soluble in acetone; insoluble in hexane
    • In tert-butanol 0.73; acetone 14.40; carbon tetrachloride 0.02; hexane 0.006; glacial acetic acid 3.10 (all in g/100 g of solvent, 25 °C)

  • Synonyms

    • n-bromobutanimide
    • RefChem:6049
    • N-Bromosuccinimide
    • 128-08-5
    • 1-Bromopyrrolidine-2,5-dione
    • Succinbromimide
    • 2,5-Pyrrolidinedione, 1-bromo-
    • Succinbromide
    • 1-Bromo-2,5-pyrrolidinedione
    • Succinibromimide
    • N-Bromosuccimide
    • NBS
    • Succinimide, N-bromo-
    • N-Bromsuccinimide
    • MFCD00005510
    • N-bromo-succinimide
    • NSC 16
    • N-Bromosuccinimide (NBS)
    • 1-Bromo-2,5-pyrrolidine-dione
    • K8G1F2UCJF
    • 1-Bromodihydro-1H-pyrrole-2,5-dione
    • 1-bromoazolidine-2,5-dione
    • NSC-16
    • n-bromo succinimide
    • CCRIS 2899
    • EINECS 204-877-2
    • UNII-K8G1F2UCJF
    • AI3-16619
    • N-Bromsuccinimid
    • N-bromosuccinimid
    • N-bromosuccmimide
    • 1-Bromo-2,5-pyrrolidinedione; Bromosuccinimide; NBS; NSC 16; Succinbromimide;
    • n-brom-succinimide
    • N-bromo succinimid
    • N-bromosuccinirnide
    • N-brornosuccinimide
    • JV-bromosuccinimide
    • N -bromosuccinimide
    • N-bromosuccin-imide
    • N- Bromosuccinimide
    • N-BromosuccinimideNBS
    • N-bromo succinic imide
    • SCHEMBL58
    • 2, 1-bromo-
    • WLN: T5VNVTJ BE
    • N-bromosuccinic acid imide
    • EC 204-877-2
    • N-bromo succinic acid imide
    • NSC16
    • 1-brompyrrolidine-2,5-dione
    • N-Bromopyrrolidine-2,5-dione
    • orb2939777
    • orb3026104
    • SCHEMBL2201542
    • SGCUT00108
    • N-BROMOSUCCINIMIDE [MI]
    • 1-Bromo-pyrrolidine-2,5-dione
    • DTXSID2038738
    • SCHEMBL10376304
    • CHEBI:53174
    • HSDB 8381
    • BB_SC-07072
    • HY-Y0775
    • to_000027
    • BR1130
    • SBB007826
    • STL146592
    • AKOS000120001
    • CS-W008781
    • FB09835
    • BP-30011
    • N-Bromosuccinimide, ReagentPlus(R), 99%
    • DB-025349
    • N-Bromosuccinimide, for synthesis, 98.0%
    • B0656
    • N-Bromosuccinimide, purum, >=95.0% (RT)
    • NS00004835
    • ST50214531
    • EN300-20081
    • D77695
    • N-Bromosuccinimide (< 0.1% wt chlorine content)
    • N-Bromosuccinimide(Discontinued,See C4X-135955)
    • Q286939
    • doi:10.14272/PCLIMKBDDGJMGD-UHFFFAOYSA-N.1
    • F1908-0173
    • InChI=1/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H
    • 128-08-5

  • Applications

    N-bromobutanimide (CAS 128-08-5) is a mild electrophilic brominating agent primarily used as a source of bromine for selective bromination in organic synthesis. It is employed for allylic and benzylic bromination and for introducing bromine into activated aromatic substrates under controlled conditions. It also serves as a convenient building-block reagent for the preparation of brominated intermediates that feed pharmaceutical and agrochemical development. In polymer and materials chemistry, it may be used to generate brominated monomers or to functionalize polymers via radical or electrophilic pathways. Additionally, it can be used in coatings, inks, and specialty chemical formulations where precise bromination steps are required in the workflow. Its use is typically governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.09
    methanol 20.0
    isopropanol 13.16
    water 2.2
    ethyl acetate 57.15
    n-propanol 12.1
    acetone 137.1
    n-butanol 10.68
    acetonitrile 106.72
    DMF 266.05
    toluene 35.8
    isobutanol 11.12
    1,4-dioxane 106.37
    methyl acetate 105.2
    THF 94.08
    2-butanone 91.24
    n-pentanol 10.97
    sec-butanol 14.27
    n-hexane 1.87
    ethylene glycol 8.44
    NMP 470.29
    cyclohexane 3.65
    DMSO 277.32
    n-butyl acetate 30.16
    n-octanol 7.78
    chloroform 110.15
    n-propyl acetate 38.71
    acetic acid 53.18
    dichloromethane 137.76
    cyclohexanone 121.49
    propylene glycol 7.52
    isopropyl acetate 37.08
    DMAc 415.62
    2-ethoxyethanol 40.42
    isopentanol 12.97
    n-heptane 1.82
    ethyl formate 55.45
    1,2-dichloroethane 87.13
    n-hexanol 8.95
    2-methoxyethanol 59.09
    isobutyl acetate 21.38
    tetrachloromethane 15.12
    n-pentyl acetate 24.31
    transcutol 80.25
    n-heptanol 6.59
    ethylbenzene 20.23
    MIBK 33.85
    2-propoxyethanol 35.21
    tert-butanol 20.1
    MTBE 29.87
    2-butoxyethanol 23.57
    propionic acid 33.85
    o-xylene 33.55
    formic acid 31.25
    diethyl ether 27.11
    m-xylene 21.68
    p-xylene 34.0
    chlorobenzene 63.73
    dimethyl carbonate 54.46
    n-octane 0.96
    formamide 88.35
    cyclopentanone 169.19
    2-pentanone 51.05
    anisole 63.69
    cyclopentyl methyl ether 44.42
    gamma-butyrolactone 215.63
    1-methoxy-2-propanol 40.11
    pyridine 141.0
    3-pentanone 60.94
    furfural 249.51
    n-dodecane 1.16
    diethylene glycol 33.38
    diisopropyl ether 10.37
    tert-amyl alcohol 21.74
    acetylacetone 122.47
    n-hexadecane 1.4
    acetophenone 84.62
    methyl propionate 63.7
    isopentyl acetate 28.38
    trichloroethylene 193.59
    n-nonanol 8.38
    cyclohexanol 19.89
    benzyl alcohol 44.25
    2-ethylhexanol 9.3
    isooctanol 6.78
    dipropyl ether 15.21
    1,2-dichlorobenzene 69.64
    ethyl lactate 28.11
    propylene carbonate 99.76
    n-methylformamide 92.19
    2-pentanol 9.87
    n-pentane 1.81
    1-propoxy-2-propanol 24.93
    1-methoxy-2-propyl acetate 45.43
    2-(2-methoxypropoxy) propanol 45.44
    mesitylene 13.98
    ε-caprolactone 98.18
    p-cymene 12.64
    epichlorohydrin 157.64
    1,1,1-trichloroethane 70.65
    2-aminoethanol 12.24
    morpholine-4-carbaldehyde 273.86
    sulfolane 285.47
    2,2,4-trimethylpentane 1.93
    2-methyltetrahydrofuran 71.81
    n-hexyl acetate 28.25
    isooctane 1.06
    2-(2-butoxyethoxy)ethanol 40.8
    sec-butyl acetate 26.58
    tert-butyl acetate 37.18
    decalin 3.55
    glycerin 17.97
    diglyme 92.14
    acrylic acid 48.16
    isopropyl myristate 16.66
    n-butyric acid 31.47
    acetyl acetate 64.55
    di(2-ethylhexyl) phthalate 23.0
    ethyl propionate 41.24
    nitromethane 270.24
    1,2-diethoxyethane 35.49
    benzonitrile 75.86
    trioctyl phosphate 14.0
    1-bromopropane 28.61
    gamma-valerolactone 246.09
    n-decanol 7.18
    triethyl phosphate 27.08
    4-methyl-2-pentanol 8.19
    propionitrile 45.12
    vinylene carbonate 106.76
    1,1,2-trichlorotrifluoroethane 115.58
    DMS 54.69
    cumene 14.71
    2-octanol 5.84
    2-hexanone 42.36
    octyl acetate 19.68
    limonene 16.36
    1,2-dimethoxyethane 108.95
    ethyl orthosilicate 21.92
    tributyl phosphate 19.3
    diacetone alcohol 43.99
    N,N-dimethylaniline 53.28
    acrylonitrile 86.24
    aniline 44.91
    1,3-propanediol 16.8
    bromobenzene 66.73
    dibromomethane 68.28
    1,1,2,2-tetrachloroethane 125.58
    2-methyl-cyclohexyl acetate 31.33
    tetrabutyl urea 31.64
    diisobutyl methanol 7.91
    2-phenylethanol 28.93
    styrene 30.37
    dioctyl adipate 30.7
    dimethyl sulfate 145.92
    ethyl butyrate 32.67
    methyl lactate 40.44
    butyl lactate 22.74
    diethyl carbonate 29.44
    propanediol butyl ether 21.39
    triethyl orthoformate 26.07
    p-tert-butyltoluene 11.48
    methyl 4-tert-butylbenzoate 51.28
    morpholine 88.34
    tert-butylamine 12.23
    n-dodecanol 6.28
    dimethoxymethane 84.16
    ethylene carbonate 73.22
    cyrene 76.67
    2-ethoxyethyl acetate 43.12
    2-ethylhexyl acetate 25.37
    1,2,4-trichlorobenzene 93.46
    4-methylpyridine 132.97
    dibutyl ether 13.46
    2,6-dimethyl-4-heptanol 7.91
    DEF 100.25
    dimethyl isosorbide 85.65
    tetrachloroethylene 79.29
    eugenol 49.02
    triacetin 55.82
    span 80 30.55
    1,4-butanediol 10.28
    1,1-dichloroethane 63.59
    2-methyl-1-pentanol 13.99
    methyl formate 98.13
    2-methyl-1-butanol 13.14
    n-decane 1.53
    butyronitrile 33.79
    3,7-dimethyl-1-octanol 10.54
    1-chlorooctane 6.78
    1-chlorotetradecane 4.28
    n-nonane 1.24
    undecane 1.32
    tert-butylcyclohexane 2.64
    cyclooctane 1.4
    cyclopentanol 26.08
    tetrahydropyran 47.32
    tert-amyl methyl ether 29.62
    2,5,8-trioxanonane 75.92
    1-hexene 6.92
    2-isopropoxyethanol 29.85
    2,2,2-trifluoroethanol 49.12
    methyl butyrate 55.74

    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