N-methyliminodiacetic acid

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  • Identifiers

    CAS number
    4408-64-4

    Molecular formula
    C5H9NO4

    SMILES
    CN(CC(=O)O)CC(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 60.6%
    Sweet 34.47%
    Savory 24.16%
    Sour 23.63%
    Meaty 18.39%
    Milky 17.81%
    Buttery 17.62%
    Cooked 16.77%
    Clean 16.72%
    Sharp 16.11%

     

    Flavor
    Odorless 65.54%
    Mild 34.14%
    Sour 32.88%
    Bland 26.83%
    Very mild 26.14%
    Acidic 24.32%
    Yeast 23.4%
    Stinky 20.97%
    Sweet-like 20.29%
    Nutty 20.27%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.3

    pKa est.
    5.76 (weak acid)

    Molecular weight
    147.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    322°C

    Flash point

    • 184.39 ˚C est.

  • Synonyms

    • N-METHYLIMINODIACETIC ACID
    • 4408-64-4
    • Glycine, N-(carboxymethyl)-N-methyl-
    • SH1YP5H4NA
    • NSC-11773
    • DTXSID00196033
    • RefChem:830727
    • DTXCID10118524
    • 2,2'-(methylazanediyl)diacetic acid
    • Methyliminodiacetic acid
    • 2-[carboxymethyl(methyl)amino]acetic acid
    • MIDA
    • MFCD00004284
    • Methylimidodiacetic acid
    • (Methylimino)diacetic acid
    • Acetic acid, (methylimino)di-
    • [(Carboxymethyl)(methyl)amino]acetic acid
    • NSC11773
    • MIDA ligand
    • N-(carboxymethyl)-N-methylGlycine
    • EINECS 224-557-6
    • NSC 11773
    • UNII-SH1YP5H4NA
    • 2-[(carboxymethyl)(methyl)amino]acetic acid
    • NCIStruc1_001758
    • NCIStruc2_000172
    • SCHEMBL22061
    • Methyliminodiacetic acid, 99%
    • orb2940340
    • SCHEMBL3898234
    • SCHEMBL5884556
    • CHEMBL1741474
    • 3-Azapentanedioic acid, 3-methyl-
    • NCI11773
    • CCG-37638
    • NCGC00013126
    • SBB053605
    • AKOS001187242
    • CS-W007872
    • FM60840
    • HY-W007872
    • NCGC00013126-02
    • NCGC00096247-01
    • 2-[(carboxymethyl)methylamino]acetic acid
    • AS-11328
    • NCI60_000423
    • SY011911
    • DB-001063
    • M2090
    • NS00031390
    • EN300-21786
    • 2-[carboxymethyl(methyl)amino]essigsäure
    • F066640
    • Z119894774
    • QuadraPure(R) IDA, macroporous, 350-750 mum particle size
    • 4408-64-4

  • Applications

    N-methyliminodiacetic acid (CAS 4408-64-4) is primarily used as a precursor to the MIDA boronate protecting group in organic synthesis, enabling the formation of MIDA boronates that facilitate Suzuki–Miyaura cross-couplings and related transformations; it also functions as a chelating ligand for metal ions, with applications in analytical chemistry (metal binding and titration) and in homogeneous catalysis; it serves as a building block for preparing metal-coordination compounds and catalysts, supporting research and development in coordination chemistry; and it provides a versatile scaffold for functionalized iminodiacetic acid derivatives used in polymer science and other materials applications where metal binding or controlled cross-linking is desired.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 20.01
    methanol 74.24
    isopropanol 5.15
    water 282.6
    ethyl acetate 3.64
    n-propanol 11.81
    acetone 3.55
    n-butanol 5.43
    acetonitrile 3.51
    DMF 142.53
    toluene 0.36
    isobutanol 4.52
    1,4-dioxane 7.33
    methyl acetate 4.54
    THF 14.19
    2-butanone 3.02
    n-pentanol 2.53
    sec-butanol 3.9
    n-hexane 0.12
    ethylene glycol 131.74
    NMP 327.19
    cyclohexane 0.11
    DMSO 86.08
    n-butyl acetate 3.93
    n-octanol 4.1
    chloroform 0.57
    n-propyl acetate 2.68
    acetic acid 102.12
    dichloromethane 1.41
    cyclohexanone 9.0
    propylene glycol 84.62
    isopropyl acetate 1.76
    DMAc 106.75
    2-ethoxyethanol 27.86
    isopentanol 2.27
    n-heptane 0.36
    ethyl formate 9.06
    1,2-dichloroethane 1.26
    n-hexanol 4.37
    2-methoxyethanol 111.1
    isobutyl acetate 1.35
    tetrachloromethane 0.16
    n-pentyl acetate 3.43
    transcutol 63.72
    n-heptanol 4.41
    ethylbenzene 0.26
    MIBK 1.33
    2-propoxyethanol 41.22
    tert-butanol 3.81
    MTBE 0.77
    2-butoxyethanol 22.17
    propionic acid 48.15
    o-xylene 0.7
    formic acid 434.88
    diethyl ether 1.04
    m-xylene 0.55
    p-xylene 0.36
    chlorobenzene 0.46
    dimethyl carbonate 10.17
    n-octane 0.16
    formamide 261.88
    cyclopentanone 16.98
    2-pentanone 2.45
    anisole 1.13
    cyclopentyl methyl ether 4.83
    gamma-butyrolactone 64.41
    1-methoxy-2-propanol 53.61
    pyridine 4.11
    3-pentanone 2.5
    furfural 57.75
    n-dodecane 0.13
    diethylene glycol 75.2
    diisopropyl ether 0.33
    tert-amyl alcohol 3.41
    acetylacetone 4.48
    n-hexadecane 0.14
    acetophenone 3.31
    methyl propionate 10.67
    isopentyl acetate 2.47
    trichloroethylene 1.79
    n-nonanol 3.74
    cyclohexanol 4.61
    benzyl alcohol 3.47
    2-ethylhexanol 2.27
    isooctanol 2.64
    dipropyl ether 2.39
    1,2-dichlorobenzene 0.8
    ethyl lactate 13.66
    propylene carbonate 24.4
    n-methylformamide 112.78
    2-pentanol 1.99
    n-pentane 0.13
    1-propoxy-2-propanol 23.63
    1-methoxy-2-propyl acetate 11.43
    2-(2-methoxypropoxy) propanol 23.97
    mesitylene 0.41
    ε-caprolactone 21.86
    p-cymene 0.81
    epichlorohydrin 14.52
    1,1,1-trichloroethane 0.32
    2-aminoethanol 133.24
    morpholine-4-carbaldehyde 174.85
    sulfolane 136.9
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 5.23
    n-hexyl acetate 5.42
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 33.05
    sec-butyl acetate 1.23
    tert-butyl acetate 1.88
    decalin 0.11
    glycerin 240.94
    diglyme 37.34
    acrylic acid 82.55
    isopropyl myristate 1.6
    n-butyric acid 21.04
    acetyl acetate 2.2
    di(2-ethylhexyl) phthalate 4.77
    ethyl propionate 3.47
    nitromethane 66.03
    1,2-diethoxyethane 3.61
    benzonitrile 2.33
    trioctyl phosphate 4.18
    1-bromopropane 0.45
    gamma-valerolactone 78.44
    n-decanol 2.7
    triethyl phosphate 3.74
    4-methyl-2-pentanol 1.01
    propionitrile 2.87
    vinylene carbonate 24.41
    1,1,2-trichlorotrifluoroethane 48.25
    DMS 8.57
    cumene 0.32
    2-octanol 2.16
    2-hexanone 1.49
    octyl acetate 3.24
    limonene 1.09
    1,2-dimethoxyethane 12.74
    ethyl orthosilicate 3.0
    tributyl phosphate 4.31
    diacetone alcohol 9.55
    N,N-dimethylaniline 2.03
    acrylonitrile 7.67
    aniline 2.37
    1,3-propanediol 58.18
    bromobenzene 0.24
    dibromomethane 0.61
    1,1,2,2-tetrachloroethane 1.84
    2-methyl-cyclohexyl acetate 3.62
    tetrabutyl urea 7.66
    diisobutyl methanol 1.16
    2-phenylethanol 4.18
    styrene 0.23
    dioctyl adipate 4.15
    dimethyl sulfate 34.74
    ethyl butyrate 3.74
    methyl lactate 44.85
    butyl lactate 13.02
    diethyl carbonate 2.64
    propanediol butyl ether 36.23
    triethyl orthoformate 3.92
    p-tert-butyltoluene 0.81
    methyl 4-tert-butylbenzoate 11.3
    morpholine 21.18
    tert-butylamine 1.31
    n-dodecanol 1.91
    dimethoxymethane 24.13
    ethylene carbonate 14.49
    cyrene 46.74
    2-ethoxyethyl acetate 7.26
    2-ethylhexyl acetate 2.21
    1,2,4-trichlorobenzene 1.4
    4-methylpyridine 3.51
    dibutyl ether 1.39
    2,6-dimethyl-4-heptanol 1.16
    DEF 17.85
    dimethyl isosorbide 34.86
    tetrachloroethylene 1.36
    eugenol 15.65
    triacetin 12.77
    span 80 27.54
    1,4-butanediol 17.39
    1,1-dichloroethane 0.43
    2-methyl-1-pentanol 1.39
    methyl formate 51.25
    2-methyl-1-butanol 3.18
    n-decane 0.21
    butyronitrile 2.04
    3,7-dimethyl-1-octanol 2.3
    1-chlorooctane 0.68
    1-chlorotetradecane 0.35
    n-nonane 0.2
    undecane 0.16
    tert-butylcyclohexane 0.11
    cyclooctane 0.09
    cyclopentanol 9.42
    tetrahydropyran 2.47
    tert-amyl methyl ether 1.33
    2,5,8-trioxanonane 31.88
    1-hexene 0.29
    2-isopropoxyethanol 9.68
    2,2,2-trifluoroethanol 54.71
    methyl butyrate 4.84

    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