Diazomethane

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  • Identifiers

    CAS number
    334-88-3

    Molecular formula
    CH2N2

    SMILES
    C=[N+]=[N-]

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 74.54%
    Pungent 59.43%
    Radish 29.49%
    Sharp 22.89%
    Alliaceous 19.7%
    Burnt 18.95%
    Sulfurous 16.84%
    Garlic 16.77%
    Bitter 13.56%
    Gassy 11.94%

     

    Flavor
    Bitter 53.9%
    Pungent 49.47%
    Mustard 49.0%
    Odorless 37.14%
    Sulfur 33.8%
    Garlic 28.35%
    Horseradish 27.19%
    Formyl 23.92%
    Strong 23.03%
    Rotten 22.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    4.31 (weak acid)

    Molecular weight
    42.04 g/mol

    Melting point expt.

    • -229 °F (NIOSH, 2024)
    • -145 °C
    • -229 °F

    Boiling point

    • -9 °F at 760 mmHg (NIOSH, 2024)
    • -23 °C
    • -9 °F

    Flash point

    • -14.05 ˚C est.
    • Flammable gas
    • NA (Gas)

    Solubility expt.

    • Reacts with water (NIOSH, 2024)
    • Soluble in ... benzene, alcohol
    • Very soluble in ether and dioxane
    • Decomposes in water
    • Solubility in water: reaction
    • Reacts

  • Synonyms

    • DIAZOMETHANE
    • Azimethylene
    • 334-88-3
    • Acomethylene
    • Methane, diazo-
    • Diazonium methylide
    • EINECS 206-382-7
    • CCRIS 205
    • HSDB 1628
    • BRN 0102415
    • DIAZOMETHANE [MI]
    • 60A625P70P
    • DIAZOMETHANE [HSDB]
    • DIAZOMETHANE [IARC]
    • DTXSID0024008
    • CHEBI:73716
    • 4-01-00-03056 (Beilstein Handbook Reference)
    • METHANE,DIAZO
    • DIAZOMETHANE (IARC)
    • azomethylene
    • diazomethan
    • diazo methane
    • diazo-methane
    • CNN radical
    • UNII-60A625P70P
    • CNN
    • DIAZOMETHYL GROUP
    • DIAZONIUM, METHYLIDE
    • Diazomethane (ACGIH:OSHA)
    • DTXCID604008
    • AKOS015901056
    • DB-264755
    • NS00029498
    • C19387
    • Q413683
    • 186581-53-3
    • 206-382-7

  • Applications

    Diazomethane (CAS 334-88-3) is used primarily as a methylene donor and methylation reagent in organic synthesis. Real-world applications include: (1) methylating carboxylic acids to form methyl esters, (2) preparation of fatty acid methyl esters for GC analysis, (3) cyclopropanation of alkenes via carbene insertion to build cyclopropane rings in complex synthetic routes, (4) generation of diazo compounds such as diazoketones from carbonyl substrates by diazomethylation for downstream transformations like Wolff rearrangement, (5) serving as a diazo source for other transformations in research and development of organic compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 17.24
    methanol 35.0
    isopropanol 10.62
    water 24.78
    ethyl acetate 25.76
    n-propanol 10.86
    acetone 46.33
    n-butanol 8.5
    acetonitrile 48.82
    DMF 128.13
    toluene 10.29
    isobutanol 9.03
    1,4-dioxane 38.47
    methyl acetate 39.69
    THF 24.17
    2-butanone 26.93
    n-pentanol 6.49
    sec-butanol 8.26
    n-hexane 2.54
    ethylene glycol 17.19
    NMP 133.98
    cyclohexane 3.49
    DMSO 64.64
    n-butyl acetate 10.76
    n-octanol 7.35
    chloroform 25.24
    n-propyl acetate 10.31
    acetic acid 35.72
    dichloromethane 31.81
    cyclohexanone 28.96
    propylene glycol 10.53
    isopropyl acetate 11.15
    DMAc 152.04
    2-ethoxyethanol 19.56
    isopentanol 7.38
    n-heptane 2.41
    ethyl formate 20.39
    1,2-dichloroethane 21.61
    n-hexanol 6.13
    2-methoxyethanol 37.59
    isobutyl acetate 6.17
    tetrachloromethane 7.27
    n-pentyl acetate 7.54
    transcutol 61.7
    n-heptanol 3.75
    ethylbenzene 6.25
    MIBK 9.11
    2-propoxyethanol 18.33
    tert-butanol 12.48
    MTBE 12.8
    2-butoxyethanol 9.47
    propionic acid 22.16
    o-xylene 13.54
    formic acid 35.33
    diethyl ether 13.15
    m-xylene 8.6
    p-xylene 9.56
    chlorobenzene 15.17
    dimethyl carbonate 21.4
    n-octane 1.23
    formamide 41.22
    cyclopentanone 34.22
    2-pentanone 15.16
    anisole 18.22
    cyclopentyl methyl ether 15.14
    gamma-butyrolactone 48.95
    1-methoxy-2-propanol 23.15
    pyridine 30.35
    3-pentanone 21.26
    furfural 63.03
    n-dodecane 1.52
    diethylene glycol 24.58
    diisopropyl ether 4.68
    tert-amyl alcohol 11.26
    acetylacetone 29.27
    n-hexadecane 1.65
    acetophenone 22.58
    methyl propionate 29.29
    isopentyl acetate 9.37
    trichloroethylene 38.32
    n-nonanol 6.74
    cyclohexanol 10.26
    benzyl alcohol 13.74
    2-ethylhexanol 5.85
    isooctanol 3.51
    dipropyl ether 8.19
    1,2-dichlorobenzene 18.96
    ethyl lactate 10.81
    propylene carbonate 24.79
    n-methylformamide 47.57
    2-pentanol 5.48
    n-pentane 2.45
    1-propoxy-2-propanol 13.39
    1-methoxy-2-propyl acetate 17.16
    2-(2-methoxypropoxy) propanol 24.88
    mesitylene 6.36
    ε-caprolactone 27.51
    p-cymene 6.29
    epichlorohydrin 33.58
    1,1,1-trichloroethane 18.46
    2-aminoethanol 16.77
    morpholine-4-carbaldehyde 94.84
    sulfolane 52.16
    2,2,4-trimethylpentane 2.12
    2-methyltetrahydrofuran 19.87
    n-hexyl acetate 12.72
    isooctane 0.98
    2-(2-butoxyethoxy)ethanol 22.4
    sec-butyl acetate 7.22
    tert-butyl acetate 11.29
    decalin 2.83
    glycerin 20.48
    diglyme 41.47
    acrylic acid 29.07
    isopropyl myristate 7.13
    n-butyric acid 15.31
    acetyl acetate 23.4
    di(2-ethylhexyl) phthalate 10.06
    ethyl propionate 15.32
    nitromethane 102.91
    1,2-diethoxyethane 17.44
    benzonitrile 20.65
    trioctyl phosphate 5.62
    1-bromopropane 9.33
    gamma-valerolactone 55.89
    n-decanol 5.54
    triethyl phosphate 10.5
    4-methyl-2-pentanol 4.07
    propionitrile 21.09
    vinylene carbonate 29.14
    1,1,2-trichlorotrifluoroethane 38.76
    DMS 26.28
    cumene 5.74
    2-octanol 3.19
    2-hexanone 9.46
    octyl acetate 9.06
    limonene 8.39
    1,2-dimethoxyethane 37.95
    ethyl orthosilicate 9.11
    tributyl phosphate 8.3
    diacetone alcohol 15.12
    N,N-dimethylaniline 19.14
    acrylonitrile 34.22
    aniline 15.85
    1,3-propanediol 15.36
    bromobenzene 13.3
    dibromomethane 17.51
    1,1,2,2-tetrachloroethane 26.86
    2-methyl-cyclohexyl acetate 11.06
    tetrabutyl urea 14.4
    diisobutyl methanol 4.64
    2-phenylethanol 10.97
    styrene 8.33
    dioctyl adipate 13.13
    dimethyl sulfate 41.35
    ethyl butyrate 12.12
    methyl lactate 20.33
    butyl lactate 8.29
    diethyl carbonate 11.35
    propanediol butyl ether 12.74
    triethyl orthoformate 10.38
    p-tert-butyltoluene 5.9
    methyl 4-tert-butylbenzoate 18.02
    morpholine 33.9
    tert-butylamine 8.37
    n-dodecanol 4.81
    dimethoxymethane 38.27
    ethylene carbonate 21.82
    cyrene 23.46
    2-ethoxyethyl acetate 14.65
    2-ethylhexyl acetate 8.32
    1,2,4-trichlorobenzene 26.37
    4-methylpyridine 31.78
    dibutyl ether 8.49
    2,6-dimethyl-4-heptanol 4.64
    DEF 40.01
    dimethyl isosorbide 31.88
    tetrachloroethylene 22.79
    eugenol 16.73
    triacetin 25.93
    span 80 15.7
    1,4-butanediol 8.32
    1,1-dichloroethane 17.34
    2-methyl-1-pentanol 6.3
    methyl formate 43.53
    2-methyl-1-butanol 7.98
    n-decane 2.02
    butyronitrile 13.27
    3,7-dimethyl-1-octanol 8.33
    1-chlorooctane 5.28
    1-chlorotetradecane 3.33
    n-nonane 1.93
    undecane 1.72
    tert-butylcyclohexane 2.46
    cyclooctane 1.58
    cyclopentanol 11.45
    tetrahydropyran 16.14
    tert-amyl methyl ether 12.52
    2,5,8-trioxanonane 38.16
    1-hexene 4.98
    2-isopropoxyethanol 12.6
    2,2,2-trifluoroethanol 27.2
    methyl butyrate 16.38

    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