Methyl isopropenyl ketone

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  • Identifiers

    CAS number
    814-78-8

    Molecular formula
    C5H8O

    SMILES
    CC(=C)C(=O)C

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Pungent 61.79%
    Ethereal 47.03%
    Sharp 40.88%
    Ketonic 40.86%
    Burnt 33.25%
    Mint 29.35%
    Caramellic 29.34%
    Camphoreous 28.65%
    Nutty 25.78%
    Musty 24.78%

    Scent© AI

    Odor threshold>

    • 0.291 ppm /inhibited/

  • Properties

    XLogP3-AA
    0.9

    Molecular weight
    84.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -65 °F (USCG, 1999)
    • -54 °C

    Boiling point

    • 208 °F at 760 mmHg (USCG, 1999)
    • 98 °C
    • 97.00 to 99.00 °C. @ 760.00 mm Hg

    Flash point est.
    3.53 ˚C

    Flash point expt.

    • less than 73 °F (USCG, 1999)
    • 9 °C
    • 49 °F CC; 9 °C CC

    Solubility expt.

    • SOL IN ALCOHOL

  • Synonyms

    • 3-Methyl-3-buten-2-one
    • 814-78-8
    • 3-Methylbut-3-en-2-one
    • Isopropenyl methyl ketone
    • METHYL ISOPROPENYL KETONE
    • 3-Buten-2-one, 3-methyl-
    • Methyl butenone
    • 2-Methyl-1-buten-3-one
    • Ketone, methyl isopropenyl
    • Propen-2-yl methyl ketone
    • 3-Methyl-3-butene-2-one
    • 3-Methyl-3-buten-2-on
    • 2-Methyl-1-butene-3-one
    • 3-Butene-2-one, 3-methyl
    • 3-Methylene-2-butanone
    • CCRIS 5317
    • HSDB 1164
    • 3-Methyl-3-buten-2-on [German]
    • EINECS 212-405-1
    • NSC 24150
    • UN1246
    • BRN 1071241
    • F64867GQVB
    • NSC-24150
    • 3-METHYL-3-BUTEN-2-ONE DIMER
    • 3-methyl-but-3-en-2-one
    • DTXSID9052557
    • CH2=C(CH3)C(=O)CH3
    • 4-01-00-03462 (Beilstein Handbook Reference)
    • METHYL-3-BUTEN-2-ONE, 3-
    • METHYL ISOPROPENYL KETONE [HSDB]
    • 3-Methyl-3-buten-2-one (stabilized with HQ)
    • 54789-11-6
    • 3-BUTEN,2-ONE,3-METHYL METHYL,ISOPROPENYL,KETONE
    • 3-Methyl-3-buten-2-on (GERMAN)
    • 3-Methyl-3-buten-2-one (Stabilized in HQ) (~90%)
    • UNII-F64867GQVB
    • 3Methyl3buten2on
    • 2Methyl1buten3one
    • 3Methyl3buten2one
    • 2Methyl1butene3one
    • 3Methyl3butene2one
    • 3Methylene2butanone
    • methylisopropenylketon
    • 3-Methyl-3-butenone
    • 3Buten2one, 3methyl
    • 3Butene2one, 3methyl
    • Propen2yl methyl ketone
    • WLN: 1VY1&U1
    • DTXCID0031130
    • 3- Methyl-3- butene-2- one
    • CHEBI:88437
    • ALBB-035703
    • NSC24150
    • Methyl isopropenyl ketone, inhibited
    • MFCD00059207
    • 3-Methyl-3-buten-2-one, AldrichCPR
    • AKOS015841085
    • UN 1246
    • DB-008321
    • M0378
    • NS00021367
    • EN300-80664
    • D87596
    • A840140
    • 3-METHYLBUT-3-EN-2-ONE(STABILIZED WITH HQ)
    • Q27160306
    • 3- Methyl-3- butene-2- one (methyl isopropenyl ketone)
    • 3-BUTEN,2-ONE,3-METHYL METHYL,ISOPROPENYL,KETONE
    • Methyl isopropenyl ketone, inhibited [UN1246] [Flammable liquid]
    • 212-405-1

  • Applications

    Methyl isopropenyl ketone (MIK, CAS 814-78-8) is a highly reactive α,β-unsaturated ketone used mainly as an intermediate and synthetic building block: in organic synthesis to access β-thio/β-amino/β-alkyl ketones via Michael addition with thiols, amines and carbon nucleophiles (e.g., organocuprates), as a dienophile in Diels–Alder reactions, and in Robinson annulation/aldol sequences to construct terpenoid, heterocyclic and pharma/agro intermediates; in materials chemistry as a monomer/comonomer or modifier to introduce enone functionality into polymers, resins, coatings and adhesives, enabling crosslinking via Michael (thiol–Michael) chemistry or photo/thermal curing to enhance adhesion and chemical resistance; it is also a precursor to certain fragrance ingredients and odorant ketones (via addition–condensation routes) and for end-group/surface functionalization in polymer research; note that MIK is a strong Michael acceptor, prone to self-polymerization and lachrymatory, so it is typically supplied with an inhibitor (e.g., hydroquinone) and requires controlled handling and storage.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1112.75
    methanol 1413.35
    isopropanol 912.89
    water 98.35
    ethyl acetate 484.34
    n-propanol 762.79
    acetone 550.26
    n-butanol 654.45
    acetonitrile 812.12
    DMF 642.1
    toluene 154.88
    isobutanol 602.56
    1,4-dioxane 651.25
    methyl acetate 655.09
    THF 541.66
    2-butanone 588.04
    n-pentanol 488.43
    sec-butanol 838.6
    n-hexane 108.22
    ethylene glycol 246.38
    NMP 458.07
    cyclohexane 47.51
    DMSO 325.01
    n-butyl acetate 155.09
    n-octanol 246.89
    chloroform 922.45
    n-propyl acetate 204.18
    acetic acid 730.66
    dichloromethane 701.64
    cyclohexanone 355.85
    propylene glycol 348.9
    isopropyl acetate 271.08
    DMAc 748.58
    2-ethoxyethanol 568.99
    isopentanol 526.99
    n-heptane 49.13
    ethyl formate 321.34
    1,2-dichloroethane 319.12
    n-hexanol 335.59
    2-methoxyethanol 815.13
    isobutyl acetate 126.39
    tetrachloromethane 272.65
    n-pentyl acetate 184.3
    transcutol 923.5
    n-heptanol 245.98
    ethylbenzene 130.32
    MIBK 214.48
    2-propoxyethanol 432.73
    tert-butanol 855.22
    MTBE 562.12
    2-butoxyethanol 351.0
    propionic acid 616.12
    o-xylene 141.72
    formic acid 429.24
    diethyl ether 501.76
    m-xylene 119.36
    p-xylene 182.81
    chlorobenzene 177.51
    dimethyl carbonate 124.07
    n-octane 28.05
    formamide 624.61
    cyclopentanone 385.6
    2-pentanone 353.1
    anisole 287.98
    cyclopentyl methyl ether 272.82
    gamma-butyrolactone 441.89
    1-methoxy-2-propanol 592.24
    pyridine 467.4
    3-pentanone 284.91
    furfural 429.96
    n-dodecane 18.96
    diethylene glycol 292.45
    diisopropyl ether 137.15
    tert-amyl alcohol 850.84
    acetylacetone 299.47
    n-hexadecane 19.79
    acetophenone 232.04
    methyl propionate 342.98
    isopentyl acetate 153.41
    trichloroethylene 575.42
    n-nonanol 207.78
    cyclohexanol 349.59
    benzyl alcohol 269.69
    2-ethylhexanol 192.94
    isooctanol 191.11
    dipropyl ether 158.96
    1,2-dichlorobenzene 161.6
    ethyl lactate 129.75
    propylene carbonate 237.18
    n-methylformamide 578.77
    2-pentanol 501.33
    n-pentane 96.36
    1-propoxy-2-propanol 277.96
    1-methoxy-2-propyl acetate 171.85
    2-(2-methoxypropoxy) propanol 255.64
    mesitylene 79.41
    ε-caprolactone 378.12
    p-cymene 70.71
    epichlorohydrin 483.86
    1,1,1-trichloroethane 492.21
    2-aminoethanol 539.75
    morpholine-4-carbaldehyde 568.31
    sulfolane 291.12
    2,2,4-trimethylpentane 63.49
    2-methyltetrahydrofuran 539.56
    n-hexyl acetate 271.4
    isooctane 34.29
    2-(2-butoxyethoxy)ethanol 362.48
    sec-butyl acetate 163.74
    tert-butyl acetate 245.19
    decalin 45.96
    glycerin 350.25
    diglyme 557.35
    acrylic acid 462.48
    isopropyl myristate 90.16
    n-butyric acid 580.35
    acetyl acetate 233.96
    di(2-ethylhexyl) phthalate 89.57
    ethyl propionate 201.26
    nitromethane 875.47
    1,2-diethoxyethane 284.99
    benzonitrile 244.01
    trioctyl phosphate 62.14
    1-bromopropane 286.83
    gamma-valerolactone 565.75
    n-decanol 137.17
    triethyl phosphate 77.74
    4-methyl-2-pentanol 258.39
    propionitrile 502.85
    vinylene carbonate 237.79
    1,1,2-trichlorotrifluoroethane 440.03
    DMS 162.88
    cumene 105.44
    2-octanol 189.35
    2-hexanone 256.02
    octyl acetate 122.32
    limonene 95.43
    1,2-dimethoxyethane 640.33
    ethyl orthosilicate 86.94
    tributyl phosphate 70.8
    diacetone alcohol 347.72
    N,N-dimethylaniline 212.13
    acrylonitrile 553.75
    aniline 288.22
    1,3-propanediol 592.93
    bromobenzene 148.4
    dibromomethane 454.73
    1,1,2,2-tetrachloroethane 480.84
    2-methyl-cyclohexyl acetate 126.62
    tetrabutyl urea 88.55
    diisobutyl methanol 100.79
    2-phenylethanol 209.25
    styrene 142.81
    dioctyl adipate 112.41
    dimethyl sulfate 155.96
    ethyl butyrate 148.69
    methyl lactate 200.74
    butyl lactate 144.82
    diethyl carbonate 99.59
    propanediol butyl ether 304.53
    triethyl orthoformate 110.9
    p-tert-butyltoluene 69.86
    methyl 4-tert-butylbenzoate 185.94
    morpholine 752.33
    tert-butylamine 563.1
    n-dodecanol 93.35
    dimethoxymethane 347.14
    ethylene carbonate 184.61
    cyrene 193.09
    2-ethoxyethyl acetate 237.87
    2-ethylhexyl acetate 122.66
    1,2,4-trichlorobenzene 213.29
    4-methylpyridine 473.9
    dibutyl ether 190.67
    2,6-dimethyl-4-heptanol 100.79
    DEF 421.65
    dimethyl isosorbide 264.38
    tetrachloroethylene 389.57
    eugenol 209.53
    triacetin 206.45
    span 80 224.66
    1,4-butanediol 271.66
    1,1-dichloroethane 534.94
    2-methyl-1-pentanol 438.8
    methyl formate 323.61
    2-methyl-1-butanol 559.17
    n-decane 36.9
    butyronitrile 455.91
    3,7-dimethyl-1-octanol 203.15
    1-chlorooctane 118.99
    1-chlorotetradecane 39.88
    n-nonane 37.77
    undecane 25.05
    tert-butylcyclohexane 61.47
    cyclooctane 21.35
    cyclopentanol 386.41
    tetrahydropyran 466.87
    tert-amyl methyl ether 415.45
    2,5,8-trioxanonane 340.82
    1-hexene 261.64
    2-isopropoxyethanol 403.63
    2,2,2-trifluoroethanol 325.09
    methyl butyrate 264.78

    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) 0.15%
Lawsonia inermis flower 1a Lawsonia inermis L. (syn. L. alba Lam.), fam. Lythraceae 0.1%