Butyllithium

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  • Identifiers

    CAS number
    109-72-8

    Molecular formula
    C4H9Li

    SMILES
    [Li].CCC[CH2]

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Cheesy 61.67%
    Fishy 54.26%
    Ripe 43.81%
    Fermented 37.38%
    Odorless 30.67%
    Oily 30.57%
    Musty 30.41%
    Sweaty 28.92%
    Alcoholic 28.87%
    Solvent 28.32%

     

    Flavor
    Fishy 43.87%
    Gasoline 30.96%
    Ammonia 28.39%
    Ammoniacal 28.08%
    Alkane 26.63%
    Rotten 25.69%
    Egg 24.99%
    Ethereal 24.0%
    Decomposing cabbage 22.96%
    Fruity 21.86%

     

  • Properties

    pKa est.
    -23.39 (strong acid)

    Molecular weight
    64.1 g/mol

    Flash point

    • -117.1 ˚C est.

  • Synonyms

    • bu-Li
    • RefChem:571855
    • DTXCID206821
    • 203-698-7
    • 09W9A6B8ZC
    • 109-72-8
    • butyl lithium
    • Butyllithium
    • CHEBI:51469
    • DTXSID1026821
    • Lithium, butyl-
    • n-BuLi
    • N-Butyllithium
    • 109-72-8

  • Applications

    Butyllithium (CAS 109-72-8) is primarily used as a strong base and nucleophile in organic synthesis to generate carbanions, enable deprotonation and lithiation for carbon-carbon bond formation, and to prepare reactive intermediates for subsequent transformations. In the polymer industry, it acts as an initiator for living (anionic) polymerization to produce well-defined polymers such as polystyrene, polybutadiene, and polyisoprene. It is also used to generate aryl/heteroaryl lithium intermediates for cross-coupling and other functionalization steps, supporting the synthesis of pharmaceutical and industrial building blocks. Additionally, it provides routes to other organolithium reagents, serving as a precursor to a range of lithiation reagents used in research and manufacturing. Handling is subject to safety and regulatory controls due to its pyrophoric nature, and use is guided by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 41.06
    methanol 39.93
    isopropanol 25.14
    water 0.26
    ethyl acetate 22.9
    n-propanol 28.05
    acetone 41.58
    n-butanol 25.57
    acetonitrile 27.84
    DMF 51.63
    toluene 10.19
    isobutanol 17.88
    1,4-dioxane 40.2
    methyl acetate 23.45
    THF 48.04
    2-butanone 27.79
    n-pentanol 17.45
    sec-butanol 21.52
    n-hexane 6.23
    ethylene glycol 13.87
    NMP 43.25
    cyclohexane 5.62
    DMSO 48.65
    n-butyl acetate 22.81
    n-octanol 14.37
    chloroform 30.2
    n-propyl acetate 15.29
    acetic acid 33.71
    dichloromethane 25.21
    cyclohexanone 34.8
    propylene glycol 14.33
    isopropyl acetate 12.33
    DMAc 26.83
    2-ethoxyethanol 19.99
    isopentanol 18.13
    n-heptane 5.5
    ethyl formate 14.21
    1,2-dichloroethane 18.75
    n-hexanol 26.44
    2-methoxyethanol 36.69
    isobutyl acetate 9.58
    tetrachloromethane 7.38
    n-pentyl acetate 12.05
    transcutol 64.04
    n-heptanol 13.16
    ethylbenzene 5.82
    MIBK 13.37
    2-propoxyethanol 31.31
    tert-butanol 25.57
    MTBE 19.42
    2-butoxyethanol 18.67
    propionic acid 26.24
    o-xylene 6.65
    formic acid 11.6
    diethyl ether 26.93
    m-xylene 7.26
    p-xylene 6.99
    chlorobenzene 13.15
    dimethyl carbonate 10.01
    n-octane 2.31
    formamide 15.65
    cyclopentanone 45.78
    2-pentanone 24.78
    anisole 13.24
    cyclopentyl methyl ether 24.28
    gamma-butyrolactone 40.46
    1-methoxy-2-propanol 29.03
    pyridine 25.74
    3-pentanone 17.08
    furfural 31.01
    n-dodecane 1.95
    diethylene glycol 26.41
    diisopropyl ether 8.04
    tert-amyl alcohol 20.57
    acetylacetone 21.48
    n-hexadecane 2.13
    acetophenone 11.67
    methyl propionate 18.55
    isopentyl acetate 16.64
    trichloroethylene 31.26
    n-nonanol 11.42
    cyclohexanol 18.9
    benzyl alcohol 10.38
    2-ethylhexanol 14.72
    isooctanol 9.78
    dipropyl ether 16.98
    1,2-dichlorobenzene 11.47
    ethyl lactate 8.14
    propylene carbonate 21.86
    n-methylformamide 25.24
    2-pentanol 17.3
    n-pentane 6.09
    1-propoxy-2-propanol 23.77
    1-methoxy-2-propyl acetate 17.66
    2-(2-methoxypropoxy) propanol 16.08
    mesitylene 5.01
    ε-caprolactone 27.6
    p-cymene 5.27
    epichlorohydrin 31.31
    1,1,1-trichloroethane 18.72
    2-aminoethanol 20.82
    morpholine-4-carbaldehyde 39.04
    sulfolane 43.3
    2,2,4-trimethylpentane 2.63
    2-methyltetrahydrofuran 36.05
    n-hexyl acetate 18.53
    isooctane 2.34
    2-(2-butoxyethoxy)ethanol 23.63
    sec-butyl acetate 9.58
    tert-butyl acetate 14.42
    decalin 2.95
    glycerin 18.09
    diglyme 37.28
    acrylic acid 23.71
    isopropyl myristate 7.83
    n-butyric acid 26.71
    acetyl acetate 13.68
    di(2-ethylhexyl) phthalate 7.0
    ethyl propionate 12.29
    nitromethane 41.63
    1,2-diethoxyethane 21.88
    benzonitrile 14.56
    trioctyl phosphate 6.02
    1-bromopropane 15.7
    gamma-valerolactone 42.22
    n-decanol 8.73
    triethyl phosphate 6.29
    4-methyl-2-pentanol 9.72
    propionitrile 19.17
    vinylene carbonate 19.52
    1,1,2-trichlorotrifluoroethane 22.33
    DMS 12.63
    cumene 4.41
    2-octanol 9.5
    2-hexanone 18.08
    octyl acetate 9.85
    limonene 9.09
    1,2-dimethoxyethane 28.27
    ethyl orthosilicate 6.28
    tributyl phosphate 7.04
    diacetone alcohol 19.24
    N,N-dimethylaniline 8.73
    acrylonitrile 22.69
    aniline 13.55
    1,3-propanediol 25.15
    bromobenzene 12.94
    dibromomethane 20.17
    1,1,2,2-tetrachloroethane 23.58
    2-methyl-cyclohexyl acetate 10.0
    tetrabutyl urea 9.3
    diisobutyl methanol 8.41
    2-phenylethanol 14.03
    styrene 7.86
    dioctyl adipate 9.52
    dimethyl sulfate 13.87
    ethyl butyrate 13.2
    methyl lactate 12.29
    butyl lactate 10.41
    diethyl carbonate 8.34
    propanediol butyl ether 18.87
    triethyl orthoformate 9.12
    p-tert-butyltoluene 5.57
    methyl 4-tert-butylbenzoate 12.25
    morpholine 42.51
    tert-butylamine 17.87
    n-dodecanol 6.98
    dimethoxymethane 26.01
    ethylene carbonate 15.62
    cyrene 12.68
    2-ethoxyethyl acetate 15.76
    2-ethylhexyl acetate 13.77
    1,2,4-trichlorobenzene 12.97
    4-methylpyridine 23.5
    dibutyl ether 14.39
    2,6-dimethyl-4-heptanol 8.41
    DEF 25.38
    dimethyl isosorbide 21.84
    tetrachloroethylene 17.63
    eugenol 12.97
    triacetin 15.03
    span 80 15.94
    1,4-butanediol 10.9
    1,1-dichloroethane 19.45
    2-methyl-1-pentanol 14.09
    methyl formate 17.51
    2-methyl-1-butanol 17.58
    n-decane 3.05
    butyronitrile 19.49
    3,7-dimethyl-1-octanol 12.08
    1-chlorooctane 9.2
    1-chlorotetradecane 3.98
    n-nonane 3.3
    undecane 2.37
    tert-butylcyclohexane 3.18
    cyclooctane 2.48
    cyclopentanol 22.52
    tetrahydropyran 35.96
    tert-amyl methyl ether 15.23
    2,5,8-trioxanonane 26.45
    1-hexene 14.83
    2-isopropoxyethanol 15.0
    2,2,2-trifluoroethanol 10.76
    methyl butyrate 16.81

    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