Dimethylmalonic acid

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  • Identifiers

    CAS number
    595-46-0

    Molecular formula
    C5H8O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sour 58.65%
    Cheesy 52.44%
    Odorless 46.14%
    Fruity 37.06%
    Sharp 33.45%
    Pungent 32.62%
    Dairy 28.86%
    Sweaty 27.51%
    Milky 25.81%
    Buttery 25.48%

     

    Flavor
    Odorless 35.39%
    Sour 30.33%
    Cheese 27.76%
    Acidic 23.13%
    Bland 21.67%
    Sharp 21.61%
    Pungent 21.34%
    Roquefort cheese 21.14%
    Soy 21.13%
    Stinky 20.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    5.56 (weak acid)

    Molecular weight
    132.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    260°C

    Melting point expt.

    • 192 °C

    Flash point

    • 147.75 ˚C est.

    Solubility expt.

    • 90 mg/mL at 13 °C

  • Synonyms

    • DIMETHYLMALONIC ACID
    • 595-46-0
    • 2,2-Dimethylmalonic acid
    • dimethylpropanedioic acid
    • Propanedioic acid, dimethyl-
    • 2,2-dimethylpropanedioic acid
    • 2,2-Propanedicarboxylic acid
    • Malonic acid, dimethyl-
    • NSC-836
    • 55981WKX6B
    • Propanedioic acid, 2,2-dimethyl-
    • DTXSID5060489
    • CHEBI:111517
    • RefChem:588570
    • DTXCID3042635
    • 209-867-1
    • MFCD00004193
    • dimethyl-malonic acid
    • 2,2-Dimethylmalonate
    • propanedioic acid dimethyl
    • 2,2-dimethyl-propanedioic acid
    • CHEMBL3360549
    • Dimethyl malonic acid
    • UNII-55981WKX6B
    • NSC 836
    • EINECS 209-867-1
    • 2,2-Propanedicarboxylate
    • DimethylmalonsA currencyure
    • Dimethylmalonic acid, 98%
    • SCHEMBL52160
    • Hydrogen 2,2-dimethylmalonate
    • NSC836
    • orb1706214
    • SCHEMBL2467558
    • SCHEMBL21830604
    • BDBM50038339
    • LMFA01170103
    • SBB065804
    • AKOS005255257
    • CS-W007894
    • EBC-613018
    • FD05620
    • HY-W007894
    • AC-22740
    • AS-12448
    • SY016494
    • DB-050524
    • D2606
    • NS00034185
    • EN300-37489
    • A10735
    • 595D460
    • AQ-917/40386832
    • F043495
    • Q27191232
    • F8881-3077
    • Dimethylmalonic acid, Standard for quantitative NMR, TraceCERT(R)
    • InChI=1/C5H8O4/c1-5(2,3(6)7)4(8)9/h1-2H3,(H,6,7)(H,8,9
    • MU6
    • Dimethylmalonic Acid

  • Applications

    Dimethylmalonic acid (dimethyl malonate) is a versatile building block in organic synthesis. It is widely used as an active methylene compound and a key intermediate for the preparation of pharmaceutical and agrochemical active ingredients. It is commonly employed in Knoevenagel condensations to furnish arylidene and heteroaryl products, which can serve as intermediates for dyes, pigments, and bioactive compounds. It also functions as a precursor in the synthesis of 1,3-dicarbonyl compounds and various heterocycles, enabling routes to specialty chemicals. In polymer and coatings chemistry, dimethylmalonate can be used as a malonate-derived monomer or functionalization reagent to introduce carbonyl linkages. Overall, its role is primarily as an intermediate and building block in multiple industrial syntheses, subject to formulation limits and regulatory considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 60.97
    methanol 100.52
    isopropanol 43.68
    water 39.8
    ethyl acetate 6.56
    n-propanol 33.01
    acetone 29.54
    n-butanol 27.21
    acetonitrile 7.07
    DMF 162.17
    toluene 1.51
    isobutanol 24.93
    1,4-dioxane 31.17
    methyl acetate 6.98
    THF 78.34
    2-butanone 14.45
    n-pentanol 20.7
    sec-butanol 29.96
    n-hexane 2.79
    ethylene glycol 39.84
    NMP 106.99
    cyclohexane 1.19
    DMSO 153.29
    n-butyl acetate 2.96
    n-octanol 11.59
    chloroform 6.41
    n-propyl acetate 4.53
    acetic acid 28.17
    dichloromethane 7.33
    cyclohexanone 15.56
    propylene glycol 37.78
    isopropyl acetate 7.83
    DMAc 96.8
    2-ethoxyethanol 61.56
    isopentanol 27.09
    n-heptane 1.83
    ethyl formate 9.81
    1,2-dichloroethane 6.91
    n-hexanol 14.61
    2-methoxyethanol 102.12
    isobutyl acetate 2.52
    tetrachloromethane 3.39
    n-pentyl acetate 6.28
    transcutol 51.69
    n-heptanol 15.48
    ethylbenzene 1.91
    MIBK 19.82
    2-propoxyethanol 40.22
    tert-butanol 70.22
    MTBE 20.93
    2-butoxyethanol 29.91
    propionic acid 15.15
    o-xylene 3.16
    formic acid 67.06
    diethyl ether 15.69
    m-xylene 3.0
    p-xylene 2.66
    chlorobenzene 1.47
    dimethyl carbonate 8.67
    n-octane 1.16
    formamide 90.41
    cyclopentanone 33.87
    2-pentanone 18.03
    anisole 7.15
    cyclopentyl methyl ether 20.74
    gamma-butyrolactone 34.61
    1-methoxy-2-propanol 86.8
    pyridine 7.08
    3-pentanone 9.95
    furfural 27.67
    n-dodecane 0.72
    diethylene glycol 47.09
    diisopropyl ether 7.25
    tert-amyl alcohol 51.22
    acetylacetone 19.76
    n-hexadecane 0.75
    acetophenone 8.58
    methyl propionate 9.8
    isopentyl acetate 4.03
    trichloroethylene 8.36
    n-nonanol 10.64
    cyclohexanol 14.3
    benzyl alcohol 9.13
    2-ethylhexanol 7.3
    isooctanol 12.85
    dipropyl ether 6.87
    1,2-dichlorobenzene 2.26
    ethyl lactate 8.43
    propylene carbonate 14.21
    n-methylformamide 56.81
    2-pentanol 23.32
    n-pentane 2.96
    1-propoxy-2-propanol 22.13
    1-methoxy-2-propyl acetate 9.28
    2-(2-methoxypropoxy) propanol 24.51
    mesitylene 3.33
    ε-caprolactone 14.47
    p-cymene 2.31
    epichlorohydrin 31.27
    1,1,1-trichloroethane 4.68
    2-aminoethanol 57.01
    morpholine-4-carbaldehyde 69.92
    sulfolane 78.59
    2,2,4-trimethylpentane 2.44
    2-methyltetrahydrofuran 29.24
    n-hexyl acetate 8.89
    isooctane 2.14
    2-(2-butoxyethoxy)ethanol 31.44
    sec-butyl acetate 3.74
    tert-butyl acetate 15.63
    decalin 1.26
    glycerin 64.11
    diglyme 47.59
    acrylic acid 16.07
    isopropyl myristate 4.35
    n-butyric acid 16.01
    acetyl acetate 4.31
    di(2-ethylhexyl) phthalate 6.26
    ethyl propionate 5.51
    nitromethane 36.2
    1,2-diethoxyethane 10.02
    benzonitrile 3.19
    trioctyl phosphate 5.49
    1-bromopropane 4.37
    gamma-valerolactone 48.01
    n-decanol 7.59
    triethyl phosphate 4.1
    4-methyl-2-pentanol 19.48
    propionitrile 5.3
    vinylene carbonate 8.74
    1,1,2-trichlorotrifluoroethane 32.3
    DMS 5.68
    cumene 2.65
    2-octanol 10.36
    2-hexanone 9.49
    octyl acetate 5.52
    limonene 3.52
    1,2-dimethoxyethane 59.07
    ethyl orthosilicate 4.31
    tributyl phosphate 4.58
    diacetone alcohol 40.43
    N,N-dimethylaniline 10.47
    acrylonitrile 6.47
    aniline 5.11
    1,3-propanediol 55.95
    bromobenzene 1.03
    dibromomethane 5.1
    1,1,2,2-tetrachloroethane 10.36
    2-methyl-cyclohexyl acetate 5.07
    tetrabutyl urea 8.84
    diisobutyl methanol 7.19
    2-phenylethanol 8.27
    styrene 1.61
    dioctyl adipate 5.82
    dimethyl sulfate 25.42
    ethyl butyrate 3.76
    methyl lactate 20.58
    butyl lactate 9.41
    diethyl carbonate 2.4
    propanediol butyl ether 28.15
    triethyl orthoformate 4.08
    p-tert-butyltoluene 2.78
    methyl 4-tert-butylbenzoate 19.34
    morpholine 47.63
    tert-butylamine 35.2
    n-dodecanol 5.31
    dimethoxymethane 78.79
    ethylene carbonate 6.84
    cyrene 34.97
    2-ethoxyethyl acetate 9.0
    2-ethylhexyl acetate 2.76
    1,2,4-trichlorobenzene 3.09
    4-methylpyridine 7.3
    dibutyl ether 5.46
    2,6-dimethyl-4-heptanol 7.19
    DEF 28.45
    dimethyl isosorbide 35.7
    tetrachloroethylene 8.58
    eugenol 16.9
    triacetin 9.48
    span 80 19.73
    1,4-butanediol 28.02
    1,1-dichloroethane 4.71
    2-methyl-1-pentanol 18.82
    methyl formate 31.99
    2-methyl-1-butanol 23.19
    n-decane 1.25
    butyronitrile 6.74
    3,7-dimethyl-1-octanol 9.76
    1-chlorooctane 3.33
    1-chlorotetradecane 1.43
    n-nonane 1.21
    undecane 0.93
    tert-butylcyclohexane 1.68
    cyclooctane 0.92
    cyclopentanol 24.72
    tetrahydropyran 14.09
    tert-amyl methyl ether 20.44
    2,5,8-trioxanonane 36.36
    1-hexene 4.84
    2-isopropoxyethanol 34.92
    2,2,2-trifluoroethanol 22.35
    methyl butyrate 7.76

    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