2,2-Dibromo-3-nitrilopropionamide

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  • Identifiers

    CAS number
    10222-01-2

    Molecular formula
    C3H2Br2N2O

    SMILES
    C(#N)C(C(=O)N)(Br)Br

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 64.28%
    Sweet 24.98%
    Savory 19.22%
    Fishy 17.18%
    Cooling 17.08%
    Bitter 17.04%
    Dry 13.81%
    Meaty 13.63%
    Mint 13.34%
    Spicy 12.94%

     

    Flavor
    Bitter 57.33%
    Odorless 41.99%
    Bland 24.75%
    Nitrile 18.79%
    Mild 18.79%
    Sweet-like 17.94%
    Taco 17.63%
    Bread crust 17.55%
    Rotten 17.46%
    Yeast 17.45%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    3.23 (weak acid)

    Molecular weight
    241.87 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 123 to 126 °C
    • 126 °C

    Boiling point

    • Decomposes at 190 °C

    Flash point

    • 109.16 ˚C est.

    Solubility expt.

    • In water, 1.5 g/100 mL (15,000 mg/L)
    • In acetone, 35 g/100 mL; in ethanol, 25 g/100mL
    • 0.82 mg/L @ 25 °C (exp)

  • Synonyms

    • 2,2-DIBROMO-2-CYANOACETAMIDE
    • 10222-01-2
    • Dibromocyanoacetamide
    • Dbnpa
    • 2,2-Dibromo-3-nitrilopropionamide
    • Acetamide, 2,2-dibromo-2-cyano-
    • 2-Cyano-2,2-dibromoacetamide
    • XD-7287l Antimicrobial
    • Caswell No. 287AA
    • Dibromonitrilopropionamide
    • 2,2-Dibromo-2-carbamoylacetonitrile
    • Dowicil QK 20
    • Dibromocyano acetic acid amide
    • NSC 98283
    • XD-1603
    • HSDB 6982
    • UNII-7N51QGL6MJ
    • XD 7287L
    • EINECS 233-539-7
    • EPA Pesticide Chemical Code 101801
    • BRN 1761192
    • DTXSID5032361
    • 2,2-Dibromo-3-nitrilopropanamide
    • Acetamide, 2-cyano-2,2-dibromo-
    • NSC-98283
    • 7N51QGL6MJ
    • DTXCID3012361
    • DOW ANTIMICROBIAL 7287
    • 3-02-00-01641 (Beilstein Handbook Reference)
    • DIBROMO-3-NITRILOPROPIONAMIDE, 2,2-
    • 2,2-DIBROMO-3-NITRILOPROPIONAMIDE [HSDB]
    • C3H2Br2N2O
    • 2,2-dibromo-2-cyano-acetamide
    • Cyanodibromoacetamide
    • MFCD00129791
    • DPNPA
    • XD7287l Antimicrobial
    • 2,2Dibromo2cyanoacetamide
    • NCIOpen2_006184
    • SCHEMBL23129
    • Acetamide, 2,2dibromo2cyano
    • Acetamide, 2cyano2,2dibromo
    • Acetamide,2-dibromo-2-cyano-
    • 2,2Dibromo2carbamoylacetonitrile
    • 2-Cyano-2,2-dibromo-Acetamide
    • CHEMBL1878278
    • DIBROMOCYANOACETAMIDE [INCI]
    • NSC98283
    • Tox21_300089
    • XD1603
    • 2,2-Dibromo-2-cyanoacetamide, 9CI
    • 2, 2-Dibromo-2-carbamoylacetonitrile
    • 2,2-Dibromo-2-cyanoacetamide, 96%
    • AKOS015833850
    • 2,2-bis(bromanyl)-2-cyano-ethanamide
    • USEPA/OPP Pesticide Code: 101801
    • alpha, alpha-Dibromo-alpha-cyanoacetamide
    • NCGC00164203-01
    • NCGC00164203-02
    • NCGC00253921-01
    • AS-12928
    • CAS-10222-01-2
    • DB-027512
    • CS-0144768
    • D2902
    • NS00009357
    • H11778
    • A800546
    • Q5204411
    • dbnpa; 2,2-dibromo-2-cyanoacetamide; 2,2-dibromo-2-carbamoylacetonitrile; 2,2-dibromo-3-nitrilopropionamide; dbnpa

  • Applications

    2,2-Dibromo-3-nitrilopropionamide is used principally as a broad-spectrum antimicrobial biocide in aqueous systems across multiple industries. In industrial settings it protects process and cooling waters from bacteria and biofilm formation; in paper and pulp processing it helps control microbial growth in process waters; in paints, coatings, and inks it serves as a preservative for water-based formulations and emulsions; in adhesives and sealants it functions as an antimicrobial preservative for aqueous product formulations; in polymers and plastics manufacturing it may be used to inhibit microbial growth in polymer emulsions and related products during processing and storage.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 44.65
    methanol 81.22
    isopropanol 39.35
    water 10.01
    ethyl acetate 54.31
    n-propanol 33.68
    acetone 193.9
    n-butanol 27.18
    acetonitrile 62.05
    DMF 573.35
    toluene 12.27
    isobutanol 23.94
    1,4-dioxane 105.21
    methyl acetate 74.34
    THF 217.55
    2-butanone 100.35
    n-pentanol 24.43
    sec-butanol 28.84
    n-hexane 2.05
    ethylene glycol 46.37
    NMP 391.86
    cyclohexane 2.85
    DMSO 426.09
    n-butyl acetate 36.36
    n-octanol 18.61
    chloroform 32.68
    n-propyl acetate 45.65
    acetic acid 65.28
    dichloromethane 32.5
    cyclohexanone 88.76
    propylene glycol 44.93
    isopropyl acetate 48.82
    DMAc 453.25
    2-ethoxyethanol 84.71
    isopentanol 22.29
    n-heptane 3.53
    ethyl formate 58.75
    1,2-dichloroethane 29.58
    n-hexanol 25.53
    2-methoxyethanol 144.45
    isobutyl acetate 28.91
    tetrachloromethane 8.21
    n-pentyl acetate 28.69
    transcutol 95.62
    n-heptanol 18.5
    ethylbenzene 7.26
    MIBK 55.16
    2-propoxyethanol 88.6
    tert-butanol 44.4
    MTBE 40.07
    2-butoxyethanol 47.58
    propionic acid 40.65
    o-xylene 11.19
    formic acid 71.96
    diethyl ether 40.56
    m-xylene 11.84
    p-xylene 10.87
    chlorobenzene 13.72
    dimethyl carbonate 91.66
    n-octane 1.84
    formamide 129.33
    cyclopentanone 186.1
    2-pentanone 83.46
    anisole 40.2
    cyclopentyl methyl ether 69.46
    gamma-butyrolactone 168.04
    1-methoxy-2-propanol 127.74
    pyridine 57.89
    3-pentanone 66.48
    furfural 155.97
    n-dodecane 1.7
    diethylene glycol 93.59
    diisopropyl ether 15.31
    tert-amyl alcohol 33.32
    acetylacetone 151.64
    n-hexadecane 1.91
    acetophenone 51.08
    methyl propionate 75.85
    isopentyl acetate 30.12
    trichloroethylene 54.64
    n-nonanol 18.05
    cyclohexanol 26.89
    benzyl alcohol 34.11
    2-ethylhexanol 16.54
    isooctanol 15.48
    dipropyl ether 27.49
    1,2-dichlorobenzene 14.55
    ethyl lactate 48.56
    propylene carbonate 87.71
    n-methylformamide 158.11
    2-pentanol 22.47
    n-pentane 2.57
    1-propoxy-2-propanol 63.99
    1-methoxy-2-propyl acetate 73.09
    2-(2-methoxypropoxy) propanol 57.3
    mesitylene 9.63
    ε-caprolactone 69.48
    p-cymene 9.06
    epichlorohydrin 118.02
    1,1,1-trichloroethane 26.23
    2-aminoethanol 47.19
    morpholine-4-carbaldehyde 257.61
    sulfolane 291.48
    2,2,4-trimethylpentane 1.85
    2-methyltetrahydrofuran 84.83
    n-hexyl acetate 31.72
    isooctane 1.6
    2-(2-butoxyethoxy)ethanol 60.9
    sec-butyl acetate 31.24
    tert-butyl acetate 59.35
    decalin 1.87
    glycerin 87.58
    diglyme 113.83
    acrylic acid 49.98
    isopropyl myristate 18.14
    n-butyric acid 41.18
    acetyl acetate 48.29
    di(2-ethylhexyl) phthalate 21.63
    ethyl propionate 46.66
    nitromethane 208.82
    1,2-diethoxyethane 41.73
    benzonitrile 29.47
    trioctyl phosphate 17.59
    1-bromopropane 13.68
    gamma-valerolactone 211.89
    n-decanol 14.65
    triethyl phosphate 26.54
    4-methyl-2-pentanol 16.39
    propionitrile 38.31
    vinylene carbonate 70.0
    1,1,2-trichlorotrifluoroethane 126.54
    DMS 42.29
    cumene 6.5
    2-octanol 14.33
    2-hexanone 55.4
    octyl acetate 22.97
    limonene 13.94
    1,2-dimethoxyethane 156.05
    ethyl orthosilicate 21.99
    tributyl phosphate 19.97
    diacetone alcohol 94.51
    N,N-dimethylaniline 39.25
    acrylonitrile 57.5
    aniline 30.28
    1,3-propanediol 53.14
    bromobenzene 10.08
    dibromomethane 17.46
    1,1,2,2-tetrachloroethane 51.96
    2-methyl-cyclohexyl acetate 32.04
    tetrabutyl urea 37.0
    diisobutyl methanol 13.69
    2-phenylethanol 32.61
    styrene 9.24
    dioctyl adipate 29.52
    dimethyl sulfate 208.36
    ethyl butyrate 35.54
    methyl lactate 87.82
    butyl lactate 35.48
    diethyl carbonate 26.68
    propanediol butyl ether 47.4
    triethyl orthoformate 30.69
    p-tert-butyltoluene 10.33
    methyl 4-tert-butylbenzoate 48.21
    morpholine 117.66
    tert-butylamine 22.99
    n-dodecanol 11.71
    dimethoxymethane 226.96
    ethylene carbonate 57.46
    cyrene 94.63
    2-ethoxyethyl acetate 43.98
    2-ethylhexyl acetate 23.82
    1,2,4-trichlorobenzene 22.31
    4-methylpyridine 55.62
    dibutyl ether 16.11
    2,6-dimethyl-4-heptanol 13.69
    DEF 123.42
    dimethyl isosorbide 112.37
    tetrachloroethylene 30.63
    eugenol 53.03
    triacetin 51.82
    span 80 42.9
    1,4-butanediol 32.6
    1,1-dichloroethane 25.83
    2-methyl-1-pentanol 18.42
    methyl formate 142.2
    2-methyl-1-butanol 20.73
    n-decane 2.5
    butyronitrile 33.23
    3,7-dimethyl-1-octanol 16.39
    1-chlorooctane 8.28
    1-chlorotetradecane 4.36
    n-nonane 2.21
    undecane 2.04
    tert-butylcyclohexane 2.0
    cyclooctane 1.49
    cyclopentanol 46.85
    tetrahydropyran 55.99
    tert-amyl methyl ether 35.56
    2,5,8-trioxanonane 95.33
    1-hexene 6.65
    2-isopropoxyethanol 58.54
    2,2,2-trifluoroethanol 66.0
    methyl butyrate 61.17

    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