2-Methyl-3-buten-1-ol

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  • Identifiers

    CAS number
    4516-90-9

    Molecular formula
    C5H10O

    SMILES
    CC(CO)C=C

    Safety labels

    Flammable
    Flammable

    Retention indicies (RI)

    • Carbowax: 1263.0

  • Odor profile

    Fruity 84.27%
    Green 61.52%
    Herbal 49.19%
    Ethereal 46.41%
    Fresh 45.98%
    Pungent 45.63%
    Fermented 44.25%
    Cheesy 37.12%
    Sharp 35.48%
    Earthy 32.33%

    Scent© AI

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    7.77 (neutral)

    Molecular weight
    86.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    128°C

    Flash point est.
    38.59 ˚C

  • Synonyms

    • 2-Methyl-3-buten-1-ol
    • 2-methylbut-3-en-1-ol
    • 4516-90-9
    • 3-Buten-1-ol, 2-methyl-
    • 2-methyl-but-3-en-1-ol
    • 2-methyl-3-butene-1-ol
    • NVGOATMUHKIQQG-UHFFFAOYSA-
    • DTXSID00863410
    • 1-hydroxy-2-methyl-3-butene
    • DTXCID10812035
    • CHEBI:165505
    • 2-Methyl-3-buten-1-ol, 98%
    • LMFA05000103
    • AKOS015912823
    • DB-051272
    • HY-147113
    • NS00123895
    • EN300-114046
    • G30485

  • Applications

    2-Methyl-3-buten-1-ol (CAS 4516-90-9) is an allylic alcohol used mainly as a versatile intermediate: it readily undergoes allylic substitution, selective oxidation, epoxidation, hydroformylation, and Tsuji–Trost reactions after conversion to carbonates/esters, making it a practical building block for preparing flavors and fragrances (notably via esterification to fruity/green acetates or carbonates), pharmaceutical and agrochemical intermediates, surfactants, and fine chemicals; in materials chemistry its OH can be functionalized to (meth)acrylates to give flexible monomers for resins/coatings, engaged in thiol–ene coupling to anchor onto polymer backbones, or serve as a precursor to unsaturated epoxides and ethers; it is also employed as a model substrate in catalytic studies (Pd, Cu, Mn, ozonolysis, etc.) to probe selectivity on allylic frameworks, and can serve as a reference/analytical standard, noting it is a flammable liquid requiring closed storage and appropriate handling.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 344.39
    methanol 382.43
    isopropanol 201.51
    water 8.12
    ethyl acetate 101.6
    n-propanol 268.76
    acetone 72.72
    n-butanol 297.98
    acetonitrile 77.5
    DMF 80.62
    toluene 13.58
    isobutanol 183.93
    1,4-dioxane 185.52
    methyl acetate 94.45
    THF 279.45
    2-butanone 98.86
    n-pentanol 167.22
    sec-butanol 196.24
    n-hexane 19.34
    ethylene glycol 81.76
    NMP 122.76
    cyclohexane 20.11
    DMSO 160.58
    n-butyl acetate 173.88
    n-octanol 73.15
    chloroform 124.93
    n-propyl acetate 80.72
    acetic acid 335.0
    dichloromethane 88.77
    cyclohexanone 153.86
    propylene glycol 100.3
    isopropyl acetate 62.12
    DMAc 72.24
    2-ethoxyethanol 171.03
    isopentanol 215.72
    n-heptane 31.29
    ethyl formate 84.93
    1,2-dichloroethane 56.28
    n-hexanol 257.66
    2-methoxyethanol 277.73
    isobutyl acetate 48.85
    tetrachloromethane 47.6
    n-pentyl acetate 72.33
    transcutol 495.36
    n-heptanol 97.18
    ethylbenzene 10.28
    MIBK 59.14
    2-propoxyethanol 249.17
    tert-butanol 233.89
    MTBE 110.18
    2-butoxyethanol 142.61
    propionic acid 211.83
    o-xylene 15.63
    formic acid 158.06
    diethyl ether 99.27
    m-xylene 15.45
    p-xylene 15.8
    chlorobenzene 32.73
    dimethyl carbonate 15.29
    n-octane 9.41
    formamide 125.48
    cyclopentanone 149.44
    2-pentanone 86.73
    anisole 34.47
    cyclopentyl methyl ether 115.6
    gamma-butyrolactone 179.21
    1-methoxy-2-propanol 169.38
    pyridine 84.53
    3-pentanone 52.77
    furfural 155.65
    n-dodecane 5.87
    diethylene glycol 182.66
    diisopropyl ether 36.05
    tert-amyl alcohol 204.56
    acetylacetone 65.84
    n-hexadecane 6.07
    acetophenone 37.71
    methyl propionate 60.7
    isopentyl acetate 128.47
    trichloroethylene 116.68
    n-nonanol 64.42
    cyclohexanol 160.66
    benzyl alcohol 45.99
    2-ethylhexanol 150.32
    isooctanol 80.4
    dipropyl ether 107.06
    1,2-dichlorobenzene 31.82
    ethyl lactate 40.03
    propylene carbonate 108.73
    n-methylformamide 93.77
    2-pentanol 163.56
    n-pentane 21.65
    1-propoxy-2-propanol 211.62
    1-methoxy-2-propyl acetate 105.44
    2-(2-methoxypropoxy) propanol 111.08
    mesitylene 13.35
    ε-caprolactone 151.69
    p-cymene 23.39
    epichlorohydrin 148.99
    1,1,1-trichloroethane 62.74
    2-aminoethanol 168.51
    morpholine-4-carbaldehyde 139.79
    sulfolane 180.9
    2,2,4-trimethylpentane 15.28
    2-methyltetrahydrofuran 236.13
    n-hexyl acetate 83.64
    isooctane 13.15
    2-(2-butoxyethoxy)ethanol 168.76
    sec-butyl acetate 51.4
    tert-butyl acetate 72.2
    decalin 9.79
    glycerin 140.93
    diglyme 236.53
    acrylic acid 150.34
    isopropyl myristate 33.83
    n-butyric acid 298.82
    acetyl acetate 52.36
    di(2-ethylhexyl) phthalate 37.61
    ethyl propionate 49.93
    nitromethane 194.76
    1,2-diethoxyethane 135.18
    benzonitrile 53.05
    trioctyl phosphate 33.02
    1-bromopropane 48.61
    gamma-valerolactone 193.97
    n-decanol 48.09
    triethyl phosphate 39.14
    4-methyl-2-pentanol 89.18
    propionitrile 79.51
    vinylene carbonate 82.98
    1,1,2-trichlorotrifluoroethane 142.56
    DMS 37.48
    cumene 13.39
    2-octanol 58.17
    2-hexanone 80.98
    octyl acetate 43.92
    limonene 44.61
    1,2-dimethoxyethane 160.76
    ethyl orthosilicate 43.19
    tributyl phosphate 38.94
    diacetone alcohol 111.36
    N,N-dimethylaniline 25.46
    acrylonitrile 75.74
    aniline 52.82
    1,3-propanediol 244.56
    bromobenzene 22.41
    dibromomethane 64.7
    1,1,2,2-tetrachloroethane 97.79
    2-methyl-cyclohexyl acetate 74.99
    tetrabutyl urea 41.68
    diisobutyl methanol 68.64
    2-phenylethanol 75.01
    styrene 11.77
    dioctyl adipate 49.34
    dimethyl sulfate 27.23
    ethyl butyrate 111.58
    methyl lactate 43.23
    butyl lactate 68.18
    diethyl carbonate 53.02
    propanediol butyl ether 117.46
    triethyl orthoformate 75.04
    p-tert-butyltoluene 22.59
    methyl 4-tert-butylbenzoate 54.86
    morpholine 230.51
    tert-butylamine 141.19
    n-dodecanol 36.99
    dimethoxymethane 56.93
    ethylene carbonate 72.33
    cyrene 77.34
    2-ethoxyethyl acetate 77.84
    2-ethylhexyl acetate 100.22
    1,2,4-trichlorobenzene 40.04
    4-methylpyridine 63.49
    dibutyl ether 67.58
    2,6-dimethyl-4-heptanol 68.64
    DEF 85.68
    dimethyl isosorbide 152.63
    tetrachloroethylene 94.11
    eugenol 66.99
    triacetin 67.44
    span 80 117.22
    1,4-butanediol 87.63
    1,1-dichloroethane 57.11
    2-methyl-1-pentanol 133.65
    methyl formate 55.53
    2-methyl-1-butanol 201.62
    n-decane 10.39
    butyronitrile 112.21
    3,7-dimethyl-1-octanol 77.61
    1-chlorooctane 30.45
    1-chlorotetradecane 12.13
    n-nonane 10.32
    undecane 7.47
    tert-butylcyclohexane 12.77
    cyclooctane 8.07
    cyclopentanol 170.35
    tetrahydropyran 193.02
    tert-amyl methyl ether 85.01
    2,5,8-trioxanonane 166.15
    1-hexene 49.28
    2-isopropoxyethanol 110.16
    2,2,2-trifluoroethanol 93.17
    methyl butyrate 80.27

    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

Botanical

Name CAS Botanical Proportion
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.04%