Methylmagnesium chloride

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  • Identifiers

    CAS number
    676-58-4

    Molecular formula
    CH3ClMg

    SMILES
    [CH3-].[Mg+2].[Cl-]

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

  • Odor profile

    Odor impact est.
    Low

  • Properties

    pKa est.
    5.39 (weak acid)

    Molecular weight
    74.79 g/mol

    Flash point

    • -94.93 ˚C est.

  • Synonyms

    • METHYLMAGNESIUM CHLORIDE
    • 676-58-4
    • Chloromethylmagnesium
    • Magnesium, chloromethyl-
    • HSDB 5740
    • EINECS 211-629-7
    • CHEBI:51492
    • EC 211-629-7
    • M5E1132G4W
    • Magnesium, chloromethyl
    • RefChem:818642
    • UN3053
    • METHYLMAGNESIUM CHLORIDE [HSDB]
    • 211-629-7
    • chloro(methyl)magnesium
    • Methyl magnesium chloride
    • MeMgCl
    • magnesium;carbanide;chloride
    • UNII-M5E1132G4W
    • CH3MgCl
    • methylmagnesiumchloride
    • Chloridomethylmagnesium
    • methyl magnesiumchloride
    • methylmagnesium-chloride
    • methyl-magnesium chloride
    • SCHEMBL5665
    • Methyl magnesium(II)chloride
    • DTXSID7052365
    • SCHEMBL25402886
    • 3M methyl magnesium chloride in THF
    • Methylmagnesium chloride, 3M in THF
    • AKOS009127739
    • Methylmagnesium chloride, 2.5M in THF
    • 676-58-4

  • Applications

    Methylmagnesium chloride (CAS 676-58-4), a methyl Grignard reagent, is widely used in organic synthesis as a nucleophilic methylating agent that adds a methyl group to carbonyl compounds to yield secondary or tertiary alcohols after aqueous workup. It can also be quenched to form hydrocarbons or higher alcohols, enabling the preparation of simple alkyl chains and alcohol products. In industry, it is used to introduce methyl groups into pharmaceutical and fine-chemical intermediates, supporting the synthesis of complex molecules in drug and agrochemical development. It can undergo carboxylation with carbon dioxide to produce carboxylic acids after acid workup, providing building blocks for carboxylic acid motifs. It also participates in epoxide opening, expanding carbon skeletons by nucleophilic attack on epoxides to yield alcohol-containing products. Thanks to these reactions, methylmagnesium chloride is a versatile building block in laboratories and contract manufacturing, though handling requires dry solvents and inert atmosphere.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 285.2
    methanol 388.01
    isopropanol 222.38
    water 3.39
    ethyl acetate 73.87
    n-propanol 216.15
    acetone 160.48
    n-butanol 195.27
    acetonitrile 134.97
    DMF 301.12
    toluene 29.19
    isobutanol 141.52
    1,4-dioxane 141.62
    methyl acetate 84.88
    THF 235.2
    2-butanone 102.21
    n-pentanol 99.3
    sec-butanol 181.07
    n-hexane 42.56
    ethylene glycol 125.27
    NMP 213.14
    cyclohexane 37.27
    DMSO 211.92
    n-butyl acetate 70.96
    n-octanol 62.47
    chloroform 217.48
    n-propyl acetate 42.23
    acetic acid 282.19
    dichloromethane 150.26
    cyclohexanone 112.99
    propylene glycol 148.8
    isopropyl acetate 39.19
    DMAc 154.48
    2-ethoxyethanol 92.47
    isopentanol 105.14
    n-heptane 29.74
    ethyl formate 75.65
    1,2-dichloroethane 85.53
    n-hexanol 138.82
    2-methoxyethanol 225.08
    isobutyl acetate 26.91
    tetrachloromethane 65.82
    n-pentyl acetate 47.21
    transcutol 127.79
    n-heptanol 69.06
    ethylbenzene 14.84
    MIBK 34.86
    2-propoxyethanol 142.14
    tert-butanol 204.86
    MTBE 95.57
    2-butoxyethanol 91.3
    propionic acid 183.41
    o-xylene 18.7
    formic acid 120.72
    diethyl ether 106.62
    m-xylene 18.45
    p-xylene 21.07
    chlorobenzene 50.08
    dimethyl carbonate 35.96
    n-octane 12.3
    formamide 113.16
    cyclopentanone 174.06
    2-pentanone 80.27
    anisole 35.16
    cyclopentyl methyl ether 84.63
    gamma-butyrolactone 192.09
    1-methoxy-2-propanol 144.81
    pyridine 116.67
    3-pentanone 57.45
    furfural 136.88
    n-dodecane 8.61
    diethylene glycol 105.76
    diisopropyl ether 25.34
    tert-amyl alcohol 159.68
    acetylacetone 57.39
    n-hexadecane 9.14
    acetophenone 29.49
    methyl propionate 70.06
    isopentyl acetate 51.69
    trichloroethylene 139.27
    n-nonanol 52.19
    cyclohexanol 110.66
    benzyl alcohol 39.5
    2-ethylhexanol 64.26
    isooctanol 46.17
    dipropyl ether 61.88
    1,2-dichlorobenzene 38.84
    ethyl lactate 30.44
    propylene carbonate 97.21
    n-methylformamide 162.31
    2-pentanol 115.54
    n-pentane 43.61
    1-propoxy-2-propanol 104.9
    1-methoxy-2-propyl acetate 45.09
    2-(2-methoxypropoxy) propanol 49.0
    mesitylene 12.84
    ε-caprolactone 92.17
    p-cymene 15.82
    epichlorohydrin 122.46
    1,1,1-trichloroethane 104.25
    2-aminoethanol 189.08
    morpholine-4-carbaldehyde 143.25
    sulfolane 197.89
    2,2,4-trimethylpentane 15.15
    2-methyltetrahydrofuran 152.07
    n-hexyl acetate 61.77
    isooctane 9.34
    2-(2-butoxyethoxy)ethanol 76.06
    sec-butyl acetate 25.17
    tert-butyl acetate 40.63
    decalin 11.07
    glycerin 154.64
    diglyme 105.68
    acrylic acid 175.01
    isopropyl myristate 25.38
    n-butyric acid 190.49
    acetyl acetate 42.72
    di(2-ethylhexyl) phthalate 28.2
    ethyl propionate 37.09
    nitromethane 190.26
    1,2-diethoxyethane 52.92
    benzonitrile 52.34
    trioctyl phosphate 24.58
    1-bromopropane 82.5
    gamma-valerolactone 153.82
    n-decanol 39.61
    triethyl phosphate 20.77
    4-methyl-2-pentanol 44.03
    propionitrile 118.43
    vinylene carbonate 83.26
    1,1,2-trichlorotrifluoroethane 135.68
    DMS 36.24
    cumene 11.38
    2-octanol 47.27
    2-hexanone 48.84
    octyl acetate 37.92
    limonene 29.0
    1,2-dimethoxyethane 108.31
    ethyl orthosilicate 21.49
    tributyl phosphate 25.72
    diacetone alcohol 61.66
    N,N-dimethylaniline 26.17
    acrylonitrile 132.75
    aniline 67.24
    1,3-propanediol 188.51
    bromobenzene 45.82
    dibromomethane 120.93
    1,1,2,2-tetrachloroethane 130.53
    2-methyl-cyclohexyl acetate 29.95
    tetrabutyl urea 32.97
    diisobutyl methanol 29.47
    2-phenylethanol 49.04
    styrene 21.84
    dioctyl adipate 31.81
    dimethyl sulfate 52.74
    ethyl butyrate 41.48
    methyl lactate 59.44
    butyl lactate 42.02
    diethyl carbonate 27.36
    propanediol butyl ether 82.87
    triethyl orthoformate 32.14
    p-tert-butyltoluene 18.02
    methyl 4-tert-butylbenzoate 42.12
    morpholine 181.09
    tert-butylamine 140.83
    n-dodecanol 30.74
    dimethoxymethane 106.03
    ethylene carbonate 69.02
    cyrene 40.8
    2-ethoxyethyl acetate 44.8
    2-ethylhexyl acetate 42.44
    1,2,4-trichlorobenzene 46.14
    4-methylpyridine 92.53
    dibutyl ether 47.11
    2,6-dimethyl-4-heptanol 29.47
    DEF 96.11
    dimethyl isosorbide 60.64
    tetrachloroethylene 97.77
    eugenol 45.15
    triacetin 40.24
    span 80 68.43
    1,4-butanediol 68.26
    1,1-dichloroethane 109.67
    2-methyl-1-pentanol 64.7
    methyl formate 98.53
    2-methyl-1-butanol 113.94
    n-decane 13.8
    butyronitrile 117.21
    3,7-dimethyl-1-octanol 43.58
    1-chlorooctane 33.89
    1-chlorotetradecane 15.12
    n-nonane 14.95
    undecane 10.4
    tert-butylcyclohexane 12.39
    cyclooctane 11.31
    cyclopentanol 162.95
    tetrahydropyran 144.12
    tert-amyl methyl ether 68.97
    2,5,8-trioxanonane 73.08
    1-hexene 75.17
    2-isopropoxyethanol 56.32
    2,2,2-trifluoroethanol 74.98
    methyl butyrate 53.44

    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