Malononitrile

Overview IFRA Request a quote

  • Identifiers

    CAS number
    109-77-3

    Molecular formula
    C3H2N2

    SMILES
    C(C#N)C#N

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 48.91%
    Sweet 37.12%
    Spicy 22.42%
    Citrus 19.38%
    Pungent 18.37%
    Fresh 18.33%
    Geranium 18.15%
    Fishy 18.05%
    Bitter 17.25%
    Dry 17.04%

     

    Flavor
    Bitter 63.34%
    Odorless 28.17%
    Nitrile 19.16%
    Rotten 17.16%
    Formyl 16.72%
    Taco 16.45%
    Bland 16.25%
    Bread crust 16.18%
    Scallion 16.12%
    Very strong 16.04%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    9.14 (weak base)

    Molecular weight
    66.06 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • 90 °F (EPA, 1998)
    • 32 °C
    • 30-34 °C
    • 90 °F

    Boiling point

    • 424 to 426 °F at 760 mmHg (EPA, 1998)
    • 218-219 °C @ 760 mm Hg
    • 218-220 °C
    • 426 °F

    Flash point

    • 103.18 ˚C est.
    • 266 °F (EPA, 1998)
    • 266 °F
    • 266 °F (OPEN CUP)
    • 112 °C o.c.
    • (oc) 266 °F

    Solubility expt.

    • greater than or equal to 100 mg/mL at 72.5 °F (NTP, 1992)
    • SOL IN ACETIC ACID, CHLOROFORM
    • Soluble in acetone and benzene
    • In water, 1.33X10+5 mg/l @ 25 °C
    • In ethanol, 0.40 g/ml @ 25 °C; in ether, 0.20 g/ml @ 25 °C
    • Solubility in water, g/100ml at 20 °C: 13.3 (moderate)
    • 13%

  • Synonyms

    • MALONONITRILE
    • Propanedinitrile
    • 109-77-3
    • Dicyanomethane
    • Malonic dinitrile
    • Methylene cyanide
    • Cyanoacetonitrile
    • Malonodinitrile
    • Dicyanmethane
    • Malonic acid dinitrile
    • Methylenedinitrile
    • Methane, dicyano-
    • Methylenecyanide
    • Propanedinitrite
    • Nitril kyseliny malonove
    • Dwumetylosulfotlenku
    • RCRA waste number U149
    • USAF A-4600
    • USAF KF-19
    • Malonsaeuredinitril
    • Nitrile kyseliny malonove
    • EBL1KKS93J
    • DTXSID6021907
    • NSC-3769
    • DTXCID701907
    • CHEBI:33186
    • DICYCANOMETHANE
    • MALONICDINITRILE
    • METHANE, DICYANO
    • RefChem:155451
    • 203-703-2
    • NSC 3769
    • MFCD00001883
    • C3H2N2
    • Methylene Dicyanide
    • Dwumetylosulfotlenku [Polish]
    • CCRIS 4663
    • HSDB 2523
    • Nitril kyseliny malonove [Czech]
    • Nitrile kyseliny malonove [Czech]
    • EINECS 203-703-2
    • UNII-EBL1KKS93J
    • UN2647
    • RCRA waste no. U149
    • BRN 0773697
    • Malononitril
    • AI3-24285
    • 1,1-dicyanomethane
    • Malononitrile, >=99%
    • WLN: NC1CN
    • MALONONITRILE [MI]
    • EC 203-703-2
    • MALONONITRILE [HSDB]
    • SCHEMBL60898
    • 4-02-00-01892 (Beilstein Handbook Reference)
    • SCHEMBL118393
    • SCHEMBL159182
    • CH2(CN)2
    • CHEMBL3187514
    • NSC3769
    • BB_SC-12704
    • Tox21_301196
    • STL168026
    • Malononitrile [UN2647] [Poison]
    • AKOS000119843
    • FM01259
    • GS-6711
    • UN 2647
    • NCGC00248329-01
    • NCGC00257529-01
    • BP-11270
    • CAS-109-77-3
    • M0033
    • NS00004975
    • EN300-19714
    • InChI=1/C3H2N2/c4-2-1-3-5/h1H
    • A15111
    • E78923
    • F075146
    • Q419572
    • Z104474890
    • 109-77-3

  • Applications

    Malononitrile (CAS 109-77-3) is a versatile activated methylene compound widely used as a building block in organic synthesis. It participates in Knoevenagel condensations with aldehydes to form arylidene malononitriles, which act as key intermediates for dyes and pigments as well as functional materials used in coatings, inks, and polymer chemistry. It is also employed as a starting material for constructing heterocycles in pharmaceutical and agrochemical research. In materials science and electronics, malononitrile derivatives serve as precursors to conjugated systems and donor–acceptor motifs for organic electronics and optoelectronic applications, and the cyano functionality enables tuning of polarity and thermal stability of materials. Use is subject to local regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.75
    methanol 42.7
    isopropanol 13.83
    water 19.04
    ethyl acetate 33.48
    n-propanol 12.5
    acetone 117.99
    n-butanol 8.15
    acetonitrile 82.31
    DMF 354.18
    toluene 8.46
    isobutanol 9.64
    1,4-dioxane 72.62
    methyl acetate 75.69
    THF 59.56
    2-butanone 46.28
    n-pentanol 7.5
    sec-butanol 9.26
    n-hexane 2.48
    ethylene glycol 40.09
    NMP 266.49
    cyclohexane 3.66
    DMSO 198.9
    n-butyl acetate 15.48
    n-octanol 9.14
    chloroform 35.16
    n-propyl acetate 19.79
    acetic acid 64.03
    dichloromethane 32.74
    cyclohexanone 39.18
    propylene glycol 26.66
    isopropyl acetate 18.14
    DMAc 335.89
    2-ethoxyethanol 28.83
    isopentanol 6.66
    n-heptane 2.77
    ethyl formate 28.16
    1,2-dichloroethane 23.06
    n-hexanol 7.65
    2-methoxyethanol 56.39
    isobutyl acetate 13.56
    tetrachloromethane 8.3
    n-pentyl acetate 12.24
    transcutol 90.67
    n-heptanol 5.61
    ethylbenzene 5.51
    MIBK 13.83
    2-propoxyethanol 28.43
    tert-butanol 16.37
    MTBE 16.18
    2-butoxyethanol 16.97
    propionic acid 39.6
    o-xylene 9.47
    formic acid 51.4
    diethyl ether 15.78
    m-xylene 6.91
    p-xylene 9.73
    chlorobenzene 15.53
    dimethyl carbonate 61.66
    n-octane 1.44
    formamide 75.08
    cyclopentanone 72.52
    2-pentanone 22.53
    anisole 24.14
    cyclopentyl methyl ether 22.31
    gamma-butyrolactone 101.34
    1-methoxy-2-propanol 37.67
    pyridine 41.71
    3-pentanone 31.89
    furfural 110.06
    n-dodecane 1.85
    diethylene glycol 43.51
    diisopropyl ether 6.37
    tert-amyl alcohol 11.63
    acetylacetone 66.57
    n-hexadecane 2.04
    acetophenone 31.14
    methyl propionate 48.06
    isopentyl acetate 12.97
    trichloroethylene 51.33
    n-nonanol 8.7
    cyclohexanol 9.3
    benzyl alcohol 15.76
    2-ethylhexanol 6.35
    isooctanol 5.06
    dipropyl ether 12.22
    1,2-dichlorobenzene 19.79
    ethyl lactate 22.2
    propylene carbonate 52.87
    n-methylformamide 100.14
    2-pentanol 5.78
    n-pentane 1.99
    1-propoxy-2-propanol 20.17
    1-methoxy-2-propyl acetate 32.82
    2-(2-methoxypropoxy) propanol 38.14
    mesitylene 5.63
    ε-caprolactone 34.73
    p-cymene 6.14
    epichlorohydrin 54.49
    1,1,1-trichloroethane 29.31
    2-aminoethanol 27.38
    morpholine-4-carbaldehyde 192.67
    sulfolane 132.28
    2,2,4-trimethylpentane 1.46
    2-methyltetrahydrofuran 29.6
    n-hexyl acetate 19.8
    isooctane 1.02
    2-(2-butoxyethoxy)ethanol 34.82
    sec-butyl acetate 12.1
    tert-butyl acetate 20.19
    decalin 2.68
    glycerin 50.82
    diglyme 73.95
    acrylic acid 61.87
    isopropyl myristate 11.23
    n-butyric acid 19.67
    acetyl acetate 45.47
    di(2-ethylhexyl) phthalate 16.66
    ethyl propionate 23.73
    nitromethane 236.15
    1,2-diethoxyethane 24.0
    benzonitrile 24.7
    trioctyl phosphate 9.81
    1-bromopropane 8.22
    gamma-valerolactone 102.13
    n-decanol 7.25
    triethyl phosphate 16.72
    4-methyl-2-pentanol 4.25
    propionitrile 26.04
    vinylene carbonate 56.5
    1,1,2-trichlorotrifluoroethane 81.7
    DMS 57.25
    cumene 5.36
    2-octanol 4.37
    2-hexanone 17.2
    octyl acetate 14.77
    limonene 8.58
    1,2-dimethoxyethane 60.91
    ethyl orthosilicate 13.33
    tributyl phosphate 12.91
    diacetone alcohol 25.81
    N,N-dimethylaniline 21.51
    acrylonitrile 49.94
    aniline 15.15
    1,3-propanediol 19.38
    bromobenzene 13.68
    dibromomethane 17.14
    1,1,2,2-tetrachloroethane 43.1
    2-methyl-cyclohexyl acetate 16.47
    tetrabutyl urea 22.87
    diisobutyl methanol 5.17
    2-phenylethanol 13.55
    styrene 8.2
    dioctyl adipate 22.49
    dimethyl sulfate 136.42
    ethyl butyrate 17.03
    methyl lactate 47.33
    butyl lactate 16.05
    diethyl carbonate 18.17
    propanediol butyl ether 24.72
    triethyl orthoformate 16.12
    p-tert-butyltoluene 6.27
    methyl 4-tert-butylbenzoate 31.0
    morpholine 54.03
    tert-butylamine 9.42
    n-dodecanol 6.33
    dimethoxymethane 84.43
    ethylene carbonate 40.05
    cyrene 44.47
    2-ethoxyethyl acetate 26.71
    2-ethylhexyl acetate 11.17
    1,2,4-trichlorobenzene 29.16
    4-methylpyridine 33.6
    dibutyl ether 10.89
    2,6-dimethyl-4-heptanol 5.17
    DEF 50.9
    dimethyl isosorbide 57.68
    tetrachloroethylene 28.79
    eugenol 29.21
    triacetin 53.91
    span 80 27.58
    1,4-butanediol 13.77
    1,1-dichloroethane 21.08
    2-methyl-1-pentanol 6.2
    methyl formate 100.86
    2-methyl-1-butanol 6.91
    n-decane 2.39
    butyronitrile 14.33
    3,7-dimethyl-1-octanol 8.97
    1-chlorooctane 6.23
    1-chlorotetradecane 4.18
    n-nonane 2.22
    undecane 2.05
    tert-butylcyclohexane 2.49
    cyclooctane 1.45
    cyclopentanol 16.21
    tetrahydropyran 24.22
    tert-amyl methyl ether 12.85
    2,5,8-trioxanonane 67.08
    1-hexene 4.79
    2-isopropoxyethanol 20.08
    2,2,2-trifluoroethanol 56.02
    methyl butyrate 26.05

    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