3-Hydroxy-4-pentenenitrile

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  • Identifiers

    CAS number
    27451-36-1

    Molecular formula
    C5H7NO

    SMILES
    C=CC(CC#N)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Green 30.29%
    Metallic 28.07%
    Spicy 26.92%
    Sweet 26.83%
    Pungent 24.64%
    Floral 24.64%
    Odorless 24.22%
    Earthy 23.3%
    Meaty 20.34%
    Fruity 19.61%

     

    Flavor
    Bitter 64.95%
    Odorless 35.46%
    Mild 21.68%
    Nitrile 21.29%
    Formyl 18.94%
    Sweet-like 18.72%
    Ocimene 18.7%
    Taco 18.65%
    Mouldy 18.6%
    Roasted peanuts 18.4%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    7.16 (neutral)

    Molecular weight
    97.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    225°C

    Flash point

    • 85.43 ˚C est.

  • Synonyms

    • 3-hydroxypent-4-enenitrile
    • 1-Cyano-2-hydroxy-3-butene
    • 27451-36-1
    • 3-Hydroxy-4-pentenenitrile
    • DTXSID20950134
    • RefChem:502442
    • DTXCID201378301
    • 827-594-1
    • 4-Pentenenitrile, 3-hydroxy-
    • 3-Hydroxy-pent-4-enenitrile
    • 6071-81-4
    • MFCD00870334
    • NSC321802;3-Hydroxypent-4-enenitrile
    • NSC321802
    • 1-Cyano-3-buten-2-ol
    • SCHEMBL2375307
    • CHEMBL1697705
    • CHEBI:166492
    • 3-Hydroxy-4-pentenenitrile, 9CI
    • (s)-1-cyano-2-hydroxy-3-butene
    • AKOS006273169
    • FC10557
    • NSC-321802
    • DB-294354
    • CS-0308277
    • EN300-113574
    • F19703
    • 27451-36-1

  • Applications

    3-Hydroxy-4-pentenenitrile (CAS 27451-36-1) is used as an organic synthesis intermediate, serving as a building block for a range of downstream compounds. Its hydroxyl and nitrile functionalities enable it to act as a monomer or a starting material for specialty polymers and resins, enabling subsequent reactions to form systems such as epoxies, polyurethanes, or acrylates. It is also regarded as a precursor for pharmaceutical and agrochemical intermediates after further transformations. In coatings and adhesive formulations, it can be used as a functional component or precursor for polymer systems with strong adhesion and crosslinking potential. These applications depend on local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 72.36
    methanol 186.9
    isopropanol 44.71
    water 56.97
    ethyl acetate 36.46
    n-propanol 47.56
    acetone 132.14
    n-butanol 30.29
    acetonitrile 67.28
    DMF 580.59
    toluene 6.55
    isobutanol 32.4
    1,4-dioxane 75.3
    methyl acetate 68.27
    THF 107.98
    2-butanone 57.08
    n-pentanol 23.56
    sec-butanol 28.54
    n-hexane 1.29
    ethylene glycol 153.9
    NMP 272.94
    cyclohexane 2.1
    DMSO 451.86
    n-butyl acetate 24.39
    n-octanol 18.45
    chloroform 27.14
    n-propyl acetate 24.11
    acetic acid 144.77
    dichloromethane 23.34
    cyclohexanone 63.24
    propylene glycol 116.52
    isopropyl acetate 20.47
    DMAc 382.33
    2-ethoxyethanol 72.09
    isopentanol 20.69
    n-heptane 2.27
    ethyl formate 47.28
    1,2-dichloroethane 20.31
    n-hexanol 28.99
    2-methoxyethanol 164.48
    isobutyl acetate 15.86
    tetrachloromethane 7.48
    n-pentyl acetate 15.94
    transcutol 157.36
    n-heptanol 16.67
    ethylbenzene 4.59
    MIBK 20.53
    2-propoxyethanol 71.26
    tert-butanol 47.85
    MTBE 19.48
    2-butoxyethanol 42.28
    propionic acid 97.85
    o-xylene 9.15
    formic acid 162.61
    diethyl ether 14.74
    m-xylene 7.71
    p-xylene 7.59
    chlorobenzene 12.65
    dimethyl carbonate 46.76
    n-octane 1.05
    formamide 171.27
    cyclopentanone 106.91
    2-pentanone 35.45
    anisole 21.85
    cyclopentyl methyl ether 28.9
    gamma-butyrolactone 120.13
    1-methoxy-2-propanol 102.15
    pyridine 47.01
    3-pentanone 30.49
    furfural 131.02
    n-dodecane 1.3
    diethylene glycol 119.4
    diisopropyl ether 5.13
    tert-amyl alcohol 31.15
    acetylacetone 68.48
    n-hexadecane 1.41
    acetophenone 31.67
    methyl propionate 51.76
    isopentyl acetate 19.19
    trichloroethylene 45.48
    n-nonanol 16.17
    cyclohexanol 26.17
    benzyl alcohol 26.66
    2-ethylhexanol 16.31
    isooctanol 12.89
    dipropyl ether 15.22
    1,2-dichlorobenzene 14.93
    ethyl lactate 35.55
    propylene carbonate 61.14
    n-methylformamide 216.31
    2-pentanol 15.23
    n-pentane 1.1
    1-propoxy-2-propanol 47.85
    1-methoxy-2-propyl acetate 38.74
    2-(2-methoxypropoxy) propanol 56.29
    mesitylene 6.25
    ε-caprolactone 47.79
    p-cymene 7.17
    epichlorohydrin 68.69
    1,1,1-trichloroethane 19.17
    2-aminoethanol 126.11
    morpholine-4-carbaldehyde 203.65
    sulfolane 185.94
    2,2,4-trimethylpentane 1.28
    2-methyltetrahydrofuran 43.39
    n-hexyl acetate 24.55
    isooctane 0.97
    2-(2-butoxyethoxy)ethanol 65.31
    sec-butyl acetate 13.84
    tert-butyl acetate 23.47
    decalin 1.84
    glycerin 201.02
    diglyme 120.83
    acrylic acid 122.23
    isopropyl myristate 12.11
    n-butyric acid 58.4
    acetyl acetate 34.56
    di(2-ethylhexyl) phthalate 19.15
    ethyl propionate 24.2
    nitromethane 268.96
    1,2-diethoxyethane 27.87
    benzonitrile 27.61
    trioctyl phosphate 14.17
    1-bromopropane 7.16
    gamma-valerolactone 133.15
    n-decanol 12.55
    triethyl phosphate 16.69
    4-methyl-2-pentanol 10.59
    propionitrile 36.2
    vinylene carbonate 58.7
    1,1,2-trichlorotrifluoroethane 131.05
    DMS 38.19
    cumene 5.16
    2-octanol 9.87
    2-hexanone 24.36
    octyl acetate 17.17
    limonene 10.41
    1,2-dimethoxyethane 100.92
    ethyl orthosilicate 14.31
    tributyl phosphate 15.86
    diacetone alcohol 50.02
    N,N-dimethylaniline 22.63
    acrylonitrile 64.61
    aniline 21.45
    1,3-propanediol 89.08
    bromobenzene 9.38
    dibromomethane 12.88
    1,1,2,2-tetrachloroethane 44.41
    2-methyl-cyclohexyl acetate 19.83
    tetrabutyl urea 26.92
    diisobutyl methanol 10.55
    2-phenylethanol 26.05
    styrene 6.15
    dioctyl adipate 23.16
    dimethyl sulfate 111.8
    ethyl butyrate 20.86
    methyl lactate 77.51
    butyl lactate 24.72
    diethyl carbonate 18.45
    propanediol butyl ether 58.93
    triethyl orthoformate 17.56
    p-tert-butyltoluene 7.14
    methyl 4-tert-butylbenzoate 33.72
    morpholine 82.66
    tert-butylamine 21.56
    n-dodecanol 10.07
    dimethoxymethane 111.22
    ethylene carbonate 44.03
    cyrene 58.35
    2-ethoxyethyl acetate 26.79
    2-ethylhexyl acetate 14.51
    1,2,4-trichlorobenzene 21.74
    4-methylpyridine 38.34
    dibutyl ether 11.8
    2,6-dimethyl-4-heptanol 10.55
    DEF 80.63
    dimethyl isosorbide 69.22
    tetrachloroethylene 31.77
    eugenol 41.7
    triacetin 45.48
    span 80 46.37
    1,4-butanediol 51.6
    1,1-dichloroethane 16.69
    2-methyl-1-pentanol 17.89
    methyl formate 153.76
    2-methyl-1-butanol 21.37
    n-decane 1.77
    butyronitrile 27.13
    3,7-dimethyl-1-octanol 15.8
    1-chlorooctane 6.77
    1-chlorotetradecane 3.64
    n-nonane 1.57
    undecane 1.48
    tert-butylcyclohexane 1.83
    cyclooctane 0.97
    cyclopentanol 45.59
    tetrahydropyran 33.25
    tert-amyl methyl ether 15.8
    2,5,8-trioxanonane 97.85
    1-hexene 4.25
    2-isopropoxyethanol 41.32
    2,2,2-trifluoroethanol 86.66
    methyl butyrate 34.88

    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