Malonic acid

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  • Identifiers

    CAS number
    141-82-2

    Molecular formula
    C3H4O4

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

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sour 68.36%
    Odorless 63.32%
    Sharp 36.48%
    Cheesy 31.29%
    Pungent 25.65%
    Burnt 23.12%
    Sweaty 21.89%
    Winey 20.86%
    Clean 20.18%
    Caramellic 19.76%

     

    Flavor
    Odorless 69.57%
    Sour 54.16%
    Vinegar 36.79%
    Acidic 32.82%
    Sharp 28.52%
    Pungent 28.1%
    Rancid 25.56%
    Soy 22.33%
    Very mild 22.28%
    Formyl 21.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.8

    pKa est.
    5.69 (weak acid)

    Molecular weight
    104.06 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 276.1 °F (NTP, 1992)
    • 135 dec °C
    • 135-137 °C
    • 135 °C

    Boiling point

    • 284 °F at 760 mmHg (decomposes) (NTP, 1992)
    • Decomposes above 140 °C

    Flash point

    • 181.01 ˚C est.

    Solubility expt.

    • greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
    • 763000 mg/L (at 25 °C)
    • In water, 6.23X10+5 mg/L at 25 °C
    • In water, 7.66X10+5 mg/L at 20 °C (pH 1-10), EU Guideline Method A.6 (flask method)
    • One gram dissolves in: 0.65 mL water, about 2 mL alcohol, 1.1 mL methanol, 3 mL propyl alcohol, 13 mL ether, 7 mL pyridine
    • 763.0 mg/mL
    • Solubility in water, g/100ml at 20 °C: 7.3

  • Synonyms

    • malonic acid
    • propanedioic acid
    • 141-82-2
    • Dicarboxymethane
    • Carboxyacetic acid
    • Methanedicarboxylic acid
    • malonate
    • Kyselina malonova
    • USAF EK-695
    • 1,3-Propanedioic acid
    • Dicarboxylic acid
    • Kyselina malonova [Czech]
    • NSC 8124
    • MFCD00002707
    • UNII-9KX7ZMG0MK
    • 9KX7ZMG0MK
    • AI3-15375
    • H2malo
    • EINECS 205-503-0
    • BRN 1751370
    • Methanedicarbonic acid
    • CHEBI:30794
    • Thallium malonate
    • HOOC-CH2-COOH
    • NSC-8124
    • Propane-1,3-dioic acid
    • Malonicacid
    • alpha,omega-Dicarboxylic acid
    • DTXSID7021659
    • HSDB 8437
    • NSC8124
    • 4-02-00-01874 (Beilstein Handbook Reference)
    • 1,3-Propanoic acid
    • Malonic acid-13C3
    • PROPANEDIOLIC ACID
    • METAHNEDICARBOXYLIC ACID
    • 2fah
    • MLI
    • Malonic acid, 99%
    • Malonic acid (8CI)
    • 1o4m
    • 63524-05-0
    • Malonate dicarboxylic acid
    • Malonic acid, 99.5%
    • Propanedioic acid (9CI)
    • SCHEMBL336
    • WLN: QV1VQ
    • MALONIC ACID [MI]
    • CH2(COOH)2
    • CHEMBL7942
    • DTXCID401659
    • SCHEMBL1471092
    • BDBM14673
    • Propanedioic acid dithallium salt
    • Malonic acid, analytical standard
    • BCP05571
    • STR00614
    • Tox21_200534
    • AC8295
    • LMFA01170041
    • s3029
    • STL194278
    • Malonic acid, ReagentPlus(R), 99%
    • AKOS000119034
    • CS-W019962
    • DB02175
    • FM32432
    • PROPANEDIOIC ACID MALONIC ACID
    • NCGC00248681-01
    • NCGC00258088-01
    • BP-11453
    • CAS-141-82-2
    • SY001875
    • DB-081008
    • DB-088240
    • Malonic acid, SAJ first grade, >=99.0%
    • M0028
    • NS00013842
    • EN300-18457
    • Malonic acid, Vetec(TM) reagent grade, 98%
    • C00383
    • C02028
    • C04025
    • Q421972
    • Z57965450
    • F1908-0177
    • Malonic acid, certified reference material, TraceCERT(R)
    • 592A9849-68C3-4635-AA3D-CBC44965EA3A
    • Malonic acid, sublimed grade, >=99.95% trace metals basis
    • DICARBOXYLIC ACID C3; PROPANEDIOLIC ACID; METHANEDICARBOXYLIC ACID
    • InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7
    • Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%
    • 205-503-0
    • 87205-08-1
    • LML

  • Applications

    Malonic acid (CAS 141-82-2) is a versatile building block in organic synthesis. In the pharmaceutical sector, it serves as a starting material for barbiturate synthesis and as a key precursor in the malonic ester pathway to access substituted carboxylic acids. In general synthetic chemistry, its esters enable Knoevenagel condensations and other reactions to prepare intermediates for fine chemicals. In agrochemicals, malonate esters derived from malonic acid are used as intermediates in the synthesis of herbicides and other crop-protection agents. It can also act as a chelating agent in analytical reagents and formulation contexts. In polymer and materials science, malonic acid and its esters are used as building blocks for functionalized polyesters and specialty monomers. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 162.88
    methanol 346.67
    isopropanol 272.73
    water 1009.65
    ethyl acetate 36.92
    n-propanol 158.43
    acetone 172.69
    n-butanol 105.5
    acetonitrile 108.7
    DMF 1349.87
    toluene 4.65
    isobutanol 136.6
    1,4-dioxane 163.26
    methyl acetate 78.67
    THF 256.08
    2-butanone 94.33
    n-pentanol 84.3
    sec-butanol 131.34
    n-hexane 4.65
    ethylene glycol 375.07
    NMP 515.55
    cyclohexane 2.17
    DMSO 798.6
    n-butyl acetate 25.85
    n-octanol 34.59
    chloroform 5.62
    n-propyl acetate 46.61
    acetic acid 170.22
    dichloromethane 8.42
    cyclohexanone 56.9
    propylene glycol 371.77
    isopropyl acetate 32.9
    DMAc 738.56
    2-ethoxyethanol 273.06
    isopentanol 81.81
    n-heptane 4.03
    ethyl formate 68.07
    1,2-dichloroethane 13.49
    n-hexanol 42.09
    2-methoxyethanol 446.96
    isobutyl acetate 31.86
    tetrachloromethane 2.63
    n-pentyl acetate 22.75
    transcutol 264.44
    n-heptanol 27.64
    ethylbenzene 3.39
    MIBK 50.84
    2-propoxyethanol 185.55
    tert-butanol 277.7
    MTBE 65.13
    2-butoxyethanol 99.45
    propionic acid 129.19
    o-xylene 6.89
    formic acid 278.84
    diethyl ether 54.01
    m-xylene 6.1
    p-xylene 5.32
    chlorobenzene 2.91
    dimethyl carbonate 113.24
    n-octane 1.82
    formamide 343.64
    cyclopentanone 123.99
    2-pentanone 66.17
    anisole 25.34
    cyclopentyl methyl ether 68.96
    gamma-butyrolactone 162.46
    1-methoxy-2-propanol 391.45
    pyridine 31.07
    3-pentanone 53.24
    furfural 119.94
    n-dodecane 1.81
    diethylene glycol 262.45
    diisopropyl ether 19.37
    tert-amyl alcohol 127.06
    acetylacetone 67.85
    n-hexadecane 1.85
    acetophenone 30.59
    methyl propionate 77.16
    isopentyl acetate 20.25
    trichloroethylene 11.39
    n-nonanol 31.77
    cyclohexanol 51.76
    benzyl alcohol 35.36
    2-ethylhexanol 17.47
    isooctanol 22.23
    dipropyl ether 39.15
    1,2-dichlorobenzene 3.17
    ethyl lactate 92.84
    propylene carbonate 72.42
    n-methylformamide 443.71
    2-pentanol 80.32
    n-pentane 5.83
    1-propoxy-2-propanol 130.78
    1-methoxy-2-propyl acetate 53.84
    2-(2-methoxypropoxy) propanol 123.08
    mesitylene 5.63
    ε-caprolactone 58.81
    p-cymene 4.63
    epichlorohydrin 99.12
    1,1,1-trichloroethane 7.41
    2-aminoethanol 376.06
    morpholine-4-carbaldehyde 445.1
    sulfolane 269.62
    2,2,4-trimethylpentane 2.8
    2-methyltetrahydrofuran 90.96
    n-hexyl acetate 32.03
    isooctane 2.65
    2-(2-butoxyethoxy)ethanol 136.91
    sec-butyl acetate 27.06
    tert-butyl acetate 42.88
    decalin 1.75
    glycerin 539.41
    diglyme 214.65
    acrylic acid 151.0
    isopropyl myristate 17.12
    n-butyric acid 74.0
    acetyl acetate 22.4
    di(2-ethylhexyl) phthalate 23.02
    ethyl propionate 44.85
    nitromethane 271.03
    1,2-diethoxyethane 51.63
    benzonitrile 18.44
    trioctyl phosphate 20.62
    1-bromopropane 7.75
    gamma-valerolactone 211.42
    n-decanol 24.81
    triethyl phosphate 21.06
    4-methyl-2-pentanol 45.46
    propionitrile 72.42
    vinylene carbonate 61.56
    1,1,2-trichlorotrifluoroethane 121.32
    DMS 36.99
    cumene 4.44
    2-octanol 20.54
    2-hexanone 55.08
    octyl acetate 24.1
    limonene 7.16
    1,2-dimethoxyethane 321.68
    ethyl orthosilicate 20.48
    tributyl phosphate 22.0
    diacetone alcohol 111.95
    N,N-dimethylaniline 32.8
    acrylonitrile 93.36
    aniline 21.6
    1,3-propanediol 258.94
    bromobenzene 1.51
    dibromomethane 5.01
    1,1,2,2-tetrachloroethane 14.05
    2-methyl-cyclohexyl acetate 22.09
    tetrabutyl urea 42.26
    diisobutyl methanol 15.97
    2-phenylethanol 22.45
    styrene 3.45
    dioctyl adipate 32.75
    dimethyl sulfate 192.26
    ethyl butyrate 28.42
    methyl lactate 177.79
    butyl lactate 45.43
    diethyl carbonate 22.94
    propanediol butyl ether 138.2
    triethyl orthoformate 28.73
    p-tert-butyltoluene 5.23
    methyl 4-tert-butylbenzoate 51.87
    morpholine 228.6
    tert-butylamine 121.61
    n-dodecanol 19.47
    dimethoxymethane 377.85
    ethylene carbonate 53.79
    cyrene 156.59
    2-ethoxyethyl acetate 35.54
    2-ethylhexyl acetate 14.0
    1,2,4-trichlorobenzene 4.8
    4-methylpyridine 32.59
    dibutyl ether 23.22
    2,6-dimethyl-4-heptanol 15.97
    DEF 130.59
    dimethyl isosorbide 136.35
    tetrachloroethylene 9.07
    eugenol 65.78
    triacetin 52.23
    span 80 81.97
    1,4-butanediol 177.43
    1,1-dichloroethane 10.45
    2-methyl-1-pentanol 50.57
    methyl formate 299.01
    2-methyl-1-butanol 79.27
    n-decane 2.71
    butyronitrile 51.39
    3,7-dimethyl-1-octanol 23.05
    1-chlorooctane 7.01
    1-chlorotetradecane 3.97
    n-nonane 2.54
    undecane 2.15
    tert-butylcyclohexane 2.36
    cyclooctane 1.28
    cyclopentanol 112.83
    tetrahydropyran 63.36
    tert-amyl methyl ether 49.93
    2,5,8-trioxanonane 185.99
    1-hexene 10.7
    2-isopropoxyethanol 169.61
    2,2,2-trifluoroethanol 156.22
    methyl butyrate 57.62

    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