3-Amino-2-butenenitrile

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  • Identifiers

    CAS number
    1118-61-2

    Molecular formula
    C4H6N2

    SMILES
    CC(=CC#N)N

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 29.85%
    Fishy 28.53%
    Meaty 26.8%
    Spicy 26.29%
    Pungent 25.17%
    Citrus 24.46%
    Roasted 22.57%
    Burnt 22.3%
    Floral 20.18%
    Metallic 19.89%

     

    Flavor
    Bitter 29.96%
    Odorless 21.4%
    Nitrile 21.26%
    Oriental 19.29%
    Mousy 18.69%
    Ocimene 18.62%
    Roasted peanuts 18.56%
    Bread crust 18.56%
    Matches 18.5%
    Mouldy 18.49%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    6.97 (neutral)

    Molecular weight
    82.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    203°C

    Flash point

    • 73.81 ˚C est.

  • Synonyms

    • 3-Aminocrotononitrile
    • 1118-61-2
    • 2-Butenenitrile, 3-amino-
    • DTXSID3061508
    • 3-Amino-2-butenenitrile
    • RefChem:1067293
    • DTXCID6033243
    • 214-266-2
    • AI3-52447
    • 3-aminobut-2-enenitrile
    • 3-Amino-but-2-enenitrile
    • beta-Aminocrotononitrile
    • 3-amino-2-butene nitrile
    • SCHEMBL294654
    • AKOS028108312
    • DB-041015
    • 1118-61-2

  • Applications

    3-Amino-2-butenenitrile is a versatile building block used chiefly as a reactive intermediate in organic synthesis. In real-world manufacturing, it is evaluated as a precursor for amine- and nitrile-containing scaffolds in pharmaceutical and agrochemical development. The compound also serves as a starting point for the synthesis of specialty polymers and plastics, where its amino and nitrile functionalities enable subsequent functionalization, crosslinking, or chain-extension steps. It can be employed in coatings, inks, and adhesive formulations as a reactive monomer or functional additive. In electronics and related high-tech sectors, it is explored as a precursor to nitrile-containing monomers and functionalized intermediates for specialty materials. Finally, it is widely used in research and development as a model substrate for studying the reactivity of amino nitrile systems and for access to diverse fine chemicals, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 45.52
    methanol 126.44
    isopropanol 26.65
    water 102.08
    ethyl acetate 29.38
    n-propanol 28.48
    acetone 111.42
    n-butanol 16.81
    acetonitrile 73.09
    DMF 297.14
    toluene 3.58
    isobutanol 18.59
    1,4-dioxane 49.34
    methyl acetate 54.96
    THF 75.4
    2-butanone 48.79
    n-pentanol 13.1
    sec-butanol 19.1
    n-hexane 1.55
    ethylene glycol 109.54
    NMP 179.07
    cyclohexane 1.59
    DMSO 154.43
    n-butyl acetate 18.27
    n-octanol 17.31
    chloroform 14.51
    n-propyl acetate 19.23
    acetic acid 185.17
    dichloromethane 10.31
    cyclohexanone 38.51
    propylene glycol 90.71
    isopropyl acetate 16.4
    DMAc 231.87
    2-ethoxyethanol 40.32
    isopentanol 11.16
    n-heptane 2.54
    ethyl formate 26.54
    1,2-dichloroethane 8.23
    n-hexanol 21.54
    2-methoxyethanol 86.87
    isobutyl acetate 14.89
    tetrachloromethane 4.83
    n-pentyl acetate 13.37
    transcutol 92.01
    n-heptanol 14.94
    ethylbenzene 2.37
    MIBK 16.47
    2-propoxyethanol 60.52
    tert-butanol 31.6
    MTBE 16.28
    2-butoxyethanol 34.88
    propionic acid 76.13
    o-xylene 4.44
    formic acid 147.66
    diethyl ether 12.59
    m-xylene 4.16
    p-xylene 4.33
    chlorobenzene 7.0
    dimethyl carbonate 49.64
    n-octane 1.05
    formamide 112.45
    cyclopentanone 73.73
    2-pentanone 27.43
    anisole 15.52
    cyclopentyl methyl ether 23.89
    gamma-butyrolactone 90.64
    1-methoxy-2-propanol 67.32
    pyridine 25.32
    3-pentanone 27.94
    furfural 79.03
    n-dodecane 1.27
    diethylene glycol 83.67
    diisopropyl ether 5.02
    tert-amyl alcohol 22.48
    acetylacetone 52.18
    n-hexadecane 1.33
    acetophenone 20.81
    methyl propionate 43.61
    isopentyl acetate 15.5
    trichloroethylene 19.97
    n-nonanol 15.66
    cyclohexanol 16.29
    benzyl alcohol 17.04
    2-ethylhexanol 12.24
    isooctanol 10.95
    dipropyl ether 14.04
    1,2-dichlorobenzene 8.18
    ethyl lactate 31.54
    propylene carbonate 46.84
    n-methylformamide 113.43
    2-pentanol 11.22
    n-pentane 1.43
    1-propoxy-2-propanol 42.71
    1-methoxy-2-propyl acetate 33.74
    2-(2-methoxypropoxy) propanol 49.17
    mesitylene 3.33
    ε-caprolactone 34.11
    p-cymene 4.94
    epichlorohydrin 40.87
    1,1,1-trichloroethane 13.61
    2-aminoethanol 82.83
    morpholine-4-carbaldehyde 125.21
    sulfolane 125.4
    2,2,4-trimethylpentane 1.37
    2-methyltetrahydrofuran 31.1
    n-hexyl acetate 23.0
    isooctane 1.0
    2-(2-butoxyethoxy)ethanol 52.58
    sec-butyl acetate 12.03
    tert-butyl acetate 20.17
    decalin 1.37
    glycerin 145.18
    diglyme 74.71
    acrylic acid 107.05
    isopropyl myristate 12.44
    n-butyric acid 39.48
    acetyl acetate 31.32
    di(2-ethylhexyl) phthalate 21.1
    ethyl propionate 20.66
    nitromethane 241.67
    1,2-diethoxyethane 18.47
    benzonitrile 17.94
    trioctyl phosphate 15.09
    1-bromopropane 3.68
    gamma-valerolactone 85.78
    n-decanol 12.59
    triethyl phosphate 14.77
    4-methyl-2-pentanol 7.93
    propionitrile 28.64
    vinylene carbonate 44.19
    1,1,2-trichlorotrifluoroethane 83.16
    DMS 36.33
    cumene 3.04
    2-octanol 8.76
    2-hexanone 19.2
    octyl acetate 18.97
    limonene 7.72
    1,2-dimethoxyethane 51.14
    ethyl orthosilicate 12.36
    tributyl phosphate 16.09
    diacetone alcohol 39.95
    N,N-dimethylaniline 14.17
    acrylonitrile 48.61
    aniline 16.08
    1,3-propanediol 46.86
    bromobenzene 4.4
    dibromomethane 5.44
    1,1,2,2-tetrachloroethane 19.51
    2-methyl-cyclohexyl acetate 18.37
    tetrabutyl urea 24.58
    diisobutyl methanol 7.24
    2-phenylethanol 21.39
    styrene 3.18
    dioctyl adipate 23.14
    dimethyl sulfate 93.89
    ethyl butyrate 16.68
    methyl lactate 63.96
    butyl lactate 23.05
    diethyl carbonate 15.68
    propanediol butyl ether 47.37
    triethyl orthoformate 14.7
    p-tert-butyltoluene 5.22
    methyl 4-tert-butylbenzoate 32.66
    morpholine 51.2
    tert-butylamine 15.63
    n-dodecanol 10.46
    dimethoxymethane 75.21
    ethylene carbonate 32.46
    cyrene 54.3
    2-ethoxyethyl acetate 24.69
    2-ethylhexyl acetate 12.07
    1,2,4-trichlorobenzene 13.94
    4-methylpyridine 21.06
    dibutyl ether 8.73
    2,6-dimethyl-4-heptanol 7.24
    DEF 40.79
    dimethyl isosorbide 61.53
    tetrachloroethylene 14.51
    eugenol 35.05
    triacetin 44.79
    span 80 48.49
    1,4-butanediol 29.49
    1,1-dichloroethane 9.87
    2-methyl-1-pentanol 9.28
    methyl formate 93.57
    2-methyl-1-butanol 12.69
    n-decane 1.7
    butyronitrile 16.44
    3,7-dimethyl-1-octanol 14.16
    1-chlorooctane 5.83
    1-chlorotetradecane 3.53
    n-nonane 1.51
    undecane 1.43
    tert-butylcyclohexane 1.6
    cyclooctane 0.8
    cyclopentanol 29.34
    tetrahydropyran 22.54
    tert-amyl methyl ether 13.86
    2,5,8-trioxanonane 71.33
    1-hexene 3.63
    2-isopropoxyethanol 27.37
    2,2,2-trifluoroethanol 96.28
    methyl butyrate 23.98

    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