Dimethyl malonate

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  • Identifiers

    CAS number
    108-59-8

    Molecular formula
    C5H8O4

    SMILES
    COC(=O)CC(=O)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1497.5

  • Odor profile

    Fruity 89.17%
    Green 72.42%
    Apple 66.2%
    Ethereal 66.11%
    Winey 63.8%
    Rummy 45.2%
    Fresh 37.0%
    Sweet 36.52%
    Sharp 35.16%
    Fermented 32.9%

    Scent© AI

  • Properties

    XLogP3-AA
    0.0

    pKa est.
    6.55 (neutral)

    Molecular weight
    132.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    183°C

    Flash point est.
    69.33 ˚C

  • Synonyms

    • Dimethyl malonate
    • 108-59-8
    • Dimethyl propanedioate
    • Methyl malonate
    • Propanedioic acid, dimethyl ester
    • Malonic Acid Dimethyl Ester
    • 1,3-dimethyl propanedioate
    • Dimethyl 1,3-propanedioate
    • CCRIS 8981
    • MALONIC ACID, DIMETHYL ESTER
    • EINECS 203-597-8
    • UNII-EM8Y79998C
    • DTXSID4029145
    • METHYL MALONATE [MI]
    • Dimethyl ester of malonic acid
    • DTXCID309145
    • EC 203-597-8
    • EM8Y79998C
    • CAS-108-59-8
    • MFCD00008460
    • Malonic acid-dimethyl ester
    • MALONIC ACID DIMETHYL ESTER (1,1,1,7,7,7-D6)
    • propanedioic acid dimethyl ester
    • Dimethyl malonate, 98%
    • malonic acid dimethylester
    • Dimethyl 1,3propanedioate
    • CH2(COOMe)2
    • SCHEMBL53913
    • CH2(CO2CH3)2
    • CHEMBL1986332
    • HY-Y1787
    • STR00450
    • Tox21_201608
    • Tox21_300375
    • BBL011438
    • NSC620046
    • STL146546
    • Dimethyl malonate, analytical standard
    • Propanedioic acid, 1,3dimethyl ester
    • AKOS001426594
    • NSC-620046
    • Propanedioic acid, 1,3-dimethyl ester
    • NCGC00248011-01
    • NCGC00248011-02
    • NCGC00254271-01
    • NCGC00259157-01
    • BP-31034
    • DA-52562
    • NCI60_005924
    • CS-0019394
    • Dimethyl malonate, purum, >=96.0% (GC)
    • M0030
    • NS00006418
    • EN300-15469
    • D72530
    • Dimethyl malonate, Vetec(TM) reagent grade, 98%
    • Q4263082
    • Z18909219
    • F0001-0174
    • PROPANEDIOIC ACID,DIMETHYL ESTER (MALONIC ACID,DIMETHYL ESTER)
    • PROPANEDIOIC ACID,DIMETHYL ESTER (MALONIC ACID,DIMETHYL ESTER)
    • 203-597-8
    • 75238-25-4

  • Applications

    Dimethyl malonate (CAS 108-59-8) is a versatile organic building block whose activated methylene between two esters underpins broad applications as a synthesis intermediate: it enables C–C bond formation via alkylation, Knoevenagel condensations and Michael additions, drives the malonic-ester route to substituted acetic acids after decarboxylation, and supports heterocycle assembly (e.g., Hantzsch dihydropyridines for calcium-channel blockers such as amlodipine and nifedipine; barbiturate scaffolds); it also feeds into agrochemicals (herbicides, fungicides, growth regulators), dyes and pigments, flavors and fragrances (e.g., cinnamate and jasmonate derivatives), and the preparation of multifunctional malonate derivatives for resins, coatings and adhesives that cure via Michael addition; after hydrolysis to malonic acid it serves as a precursor to chelating/coordination materials, and it is widely used as a model substrate in asymmetric catalysis and fine-chemical method development owing to its high reactivity, reliability and scalability.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 137.2
    methanol 273.25
    isopropanol 114.88
    water 54.44
    ethyl acetate 83.19
    n-propanol 76.17
    acetone 161.07
    n-butanol 62.38
    acetonitrile 131.21
    DMF 543.15
    toluene 53.68
    isobutanol 55.04
    1,4-dioxane 311.95
    methyl acetate 160.27
    THF 276.03
    2-butanone 93.03
    n-pentanol 31.48
    sec-butanol 64.22
    n-hexane 4.74
    ethylene glycol 89.98
    NMP 454.47
    cyclohexane 16.4
    DMSO 444.72
    n-butyl acetate 18.32
    n-octanol 15.93
    chloroform 262.31
    n-propyl acetate 24.39
    acetic acid 111.69
    dichloromethane 262.04
    cyclohexanone 118.61
    propylene glycol 73.75
    isopropyl acetate 34.83
    DMAc 595.74
    2-ethoxyethanol 102.11
    isopentanol 43.14
    n-heptane 3.22
    ethyl formate 138.24
    1,2-dichloroethane 129.79
    n-hexanol 20.02
    2-methoxyethanol 322.45
    isobutyl acetate 13.55
    tetrachloromethane 52.16
    n-pentyl acetate 13.6
    transcutol 97.12
    n-heptanol 11.83
    ethylbenzene 23.47
    MIBK 27.17
    2-propoxyethanol 67.41
    tert-butanol 124.34
    MTBE 54.77
    2-butoxyethanol 32.27
    propionic acid 82.45
    o-xylene 45.4
    formic acid 196.38
    diethyl ether 58.14
    m-xylene 29.91
    p-xylene 35.85
    chlorobenzene 59.9
    dimethyl carbonate 84.28
    n-octane 1.78
    formamide 299.05
    cyclopentanone 147.68
    2-pentanone 51.98
    anisole 68.11
    cyclopentyl methyl ether 82.47
    gamma-butyrolactone 216.76
    1-methoxy-2-propanol 171.73
    pyridine 180.63
    3-pentanone 51.22
    furfural 304.15
    n-dodecane 2.05
    diethylene glycol 88.45
    diisopropyl ether 11.34
    tert-amyl alcohol 68.62
    acetylacetone 76.47
    n-hexadecane 2.34
    acetophenone 59.57
    methyl propionate 102.41
    isopentyl acetate 16.56
    trichloroethylene 204.61
    n-nonanol 14.76
    cyclohexanol 73.71
    benzyl alcohol 67.94
    2-ethylhexanol 11.96
    isooctanol 9.86
    dipropyl ether 16.35
    1,2-dichlorobenzene 58.13
    ethyl lactate 28.52
    propylene carbonate 102.36
    n-methylformamide 292.64
    2-pentanol 29.55
    n-pentane 5.96
    1-propoxy-2-propanol 34.91
    1-methoxy-2-propyl acetate 34.13
    2-(2-methoxypropoxy) propanol 41.22
    mesitylene 17.72
    ε-caprolactone 100.97
    p-cymene 10.98
    epichlorohydrin 221.58
    1,1,1-trichloroethane 112.39
    2-aminoethanol 105.0
    morpholine-4-carbaldehyde 355.9
    sulfolane 228.96
    2,2,4-trimethylpentane 3.26
    2-methyltetrahydrofuran 147.44
    n-hexyl acetate 21.82
    isooctane 1.72
    2-(2-butoxyethoxy)ethanol 43.19
    sec-butyl acetate 15.49
    tert-butyl acetate 30.19
    decalin 7.21
    glycerin 133.68
    diglyme 114.88
    acrylic acid 87.93
    isopropyl myristate 9.61
    n-butyric acid 73.41
    acetyl acetate 54.52
    di(2-ethylhexyl) phthalate 14.14
    ethyl propionate 35.1
    nitromethane 303.55
    1,2-diethoxyethane 28.71
    benzonitrile 68.22
    trioctyl phosphate 8.75
    1-bromopropane 54.03
    gamma-valerolactone 258.81
    n-decanol 10.99
    triethyl phosphate 20.16
    4-methyl-2-pentanol 16.46
    propionitrile 78.57
    vinylene carbonate 117.83
    1,1,2-trichlorotrifluoroethane 215.3
    DMS 36.98
    cumene 16.05
    2-octanol 8.87
    2-hexanone 24.5
    octyl acetate 13.24
    limonene 15.01
    1,2-dimethoxyethane 220.43
    ethyl orthosilicate 18.17
    tributyl phosphate 10.61
    diacetone alcohol 52.76
    N,N-dimethylaniline 58.13
    acrylonitrile 116.15
    aniline 103.59
    1,3-propanediol 131.32
    bromobenzene 54.49
    dibromomethane 143.89
    1,1,2,2-tetrachloroethane 195.04
    2-methyl-cyclohexyl acetate 19.15
    tetrabutyl urea 20.55
    diisobutyl methanol 8.58
    2-phenylethanol 34.12
    styrene 30.78
    dioctyl adipate 17.45
    dimethyl sulfate 153.56
    ethyl butyrate 19.86
    methyl lactate 80.71
    butyl lactate 15.71
    diethyl carbonate 20.78
    propanediol butyl ether 33.32
    triethyl orthoformate 19.62
    p-tert-butyltoluene 11.36
    methyl 4-tert-butylbenzoate 42.0
    morpholine 311.27
    tert-butylamine 65.17
    n-dodecanol 8.77
    dimethoxymethane 244.24
    ethylene carbonate 89.68
    cyrene 61.03
    2-ethoxyethyl acetate 25.79
    2-ethylhexyl acetate 12.71
    1,2,4-trichlorobenzene 72.99
    4-methylpyridine 181.93
    dibutyl ether 14.66
    2,6-dimethyl-4-heptanol 8.58
    DEF 129.62
    dimethyl isosorbide 66.33
    tetrachloroethylene 129.98
    eugenol 38.12
    triacetin 31.88
    span 80 27.27
    1,4-butanediol 43.58
    1,1-dichloroethane 118.76
    2-methyl-1-pentanol 24.46
    methyl formate 269.42
    2-methyl-1-butanol 41.17
    n-decane 3.13
    butyronitrile 64.6
    3,7-dimethyl-1-octanol 14.47
    1-chlorooctane 10.53
    1-chlorotetradecane 5.18
    n-nonane 2.87
    undecane 2.45
    tert-butylcyclohexane 5.27
    cyclooctane 4.43
    cyclopentanol 92.68
    tetrahydropyran 134.16
    tert-amyl methyl ether 41.87
    2,5,8-trioxanonane 81.96
    1-hexene 12.53
    2-isopropoxyethanol 49.79
    2,2,2-trifluoroethanol 102.85
    methyl butyrate 49.35

    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

Botanical

Name CAS Botanical Proportion
Myrtle berry (Italy) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.05%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 0.71%