Cyanoacetic acid

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  • Identifiers

    CAS number
    372-09-8

    Molecular formula
    C3H3NO2

    SMILES
    C(C#N)C(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 55.41%
    Sour 26.17%
    Burnt 21.67%
    Roasted 20.88%
    Meaty 20.4%
    Sharp 20.18%
    Pungent 19.76%
    Cheesy 19.24%
    Sulfurous 18.29%
    Cooked 18.21%

     

    Flavor
    Odorless 65.0%
    Mild 31.74%
    Sour 25.85%
    Bland 23.47%
    Very mild 22.46%
    Yeast 21.88%
    Bitter 21.45%
    Mousy 20.32%
    Formyl 20.21%
    Faint 19.93%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.8

    pKa est.
    6.4 (neutral)

    Molecular weight
    85.06 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 151 °F (USCG, 1999)
    • 66 °C

    Boiling point

    • 108 °C at 15 mm Hg

    Flash point

    • 123.25 ˚C est.

    Solubility expt.

    • Sol in water, alcohol, ether; slightly sol in benzene, chloroform
    • Slightly sol in acetic acid

  • Synonyms

    • CYANOACETIC ACID
    • 372-09-8
    • 2-Cyanoacetic acid
    • Acetic acid, cyano-
    • Malonic mononitrile
    • Acide cyanacetique
    • Cyanessigsaeure
    • Cyanoaceticacid
    • Monocyanoacetic acid
    • Malonic acid mononitrile
    • cyanoethanoic acid
    • USAF KF-17
    • Kyselina kyanoctova
    • Cyanessigsaeure [German]
    • Acide cyanacetique [French]
    • Kyselina kyanoctova [Czech]
    • NSC 5571
    • HSDB 272
    • cyanacetic acid
    • Acetic acid, 2-cyano-
    • EINECS 206-743-9
    • UNII-QZT550H2Y9
    • MFCD00002677
    • BRN 0506325
    • QZT550H2Y9
    • DTXSID0027149
    • CHEBI:51889
    • AI3-15026
    • NCCH2COOH
    • NSC-5571
    • CYANOACETIC ACID [MI]
    • DTXCID707149
    • CYANOACETIC ACID [HSDB]
    • EC 206-743-9
    • 4-02-00-01888 (Beilstein Handbook Reference)
    • ACIDE CYANACETIQUE (FRENCH)
    • CAS-372-09-8
    • CYANOCETIC ACID
    • cyano acetic acid
    • cyano-acetic acid
    • 2-Cyanoacetic Acid; Cyanoethanoic Acid; Malonic Mononitrile; Monocyanoacetic Acid; NSC 5571
    • acetic acid, cyano
    • alphacyanoacetic acid
    • 2-cyano-acetic acid
    • Acetic acid, 2cyano
    • alpha cyanoacetic acid
    • alpha-cyanoacetic acid
    • MALONIC NITRILE
    • Cyanoacetic acid, 99%
    • WLN: QV1CN
    • Cyanoacetic acid, >=99%
    • CHEMBL3185860
    • NSC5571
    • Cyanoacetic acid (acd/name 4.0)
    • STR00053
    • Tox21_201645
    • Tox21_303155
    • STL146616
    • AKOS000119706
    • FC10719
    • FC61392
    • Cyanoacetic acid - 70% aqueous solution
    • NCGC00249091-01
    • NCGC00257182-01
    • NCGC00259194-01
    • NS00004053
    • EN300-19926
    • P20002
    • Q1146963
    • F2191-0053
    • Z104476112
    • 206-743-9

  • Applications

    Cyanoacetic acid (CAS 372-09-8) is a versatile synthetic building block with real-world relevance across several industries: it serves as a key precursor to cyanoacrylate monomers used in fast-setting adhesives; it is employed as an intermediate in the synthesis of heterocycles and amino acid derivatives for pharmaceutical research; it acts as a building block for nitrile-containing polymers and functionalized plastics; it is used to manufacture coatings and inks through nitrile-containing monomers; it is explored in agricultural chemical development as a precursor to herbicides and related agrochemicals; and it supports advanced materials and electronics applications as a source of functionalized monomer units.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 43.5
    methanol 121.29
    isopropanol 34.31
    water 287.7
    ethyl acetate 18.25
    n-propanol 26.63
    acetone 116.62
    n-butanol 16.7
    acetonitrile 84.65
    DMF 841.57
    toluene 1.43
    isobutanol 21.11
    1,4-dioxane 50.34
    methyl acetate 52.13
    THF 65.09
    2-butanone 43.78
    n-pentanol 15.63
    sec-butanol 17.93
    n-hexane 0.81
    ethylene glycol 155.4
    NMP 299.75
    cyclohexane 0.45
    DMSO 361.17
    n-butyl acetate 11.86
    n-octanol 11.01
    chloroform 2.26
    n-propyl acetate 20.83
    acetic acid 94.06
    dichloromethane 2.96
    cyclohexanone 24.35
    propylene glycol 111.45
    isopropyl acetate 12.92
    DMAc 570.35
    2-ethoxyethanol 88.87
    isopentanol 14.44
    n-heptane 0.86
    ethyl formate 35.98
    1,2-dichloroethane 4.47
    n-hexanol 9.59
    2-methoxyethanol 162.14
    isobutyl acetate 14.2
    tetrachloromethane 0.91
    n-pentyl acetate 9.88
    transcutol 107.47
    n-heptanol 8.4
    ethylbenzene 1.57
    MIBK 17.33
    2-propoxyethanol 57.88
    tert-butanol 39.38
    MTBE 16.09
    2-butoxyethanol 34.33
    propionic acid 51.3
    o-xylene 2.68
    formic acid 160.33
    diethyl ether 11.36
    m-xylene 2.19
    p-xylene 2.74
    chlorobenzene 1.51
    dimethyl carbonate 62.37
    n-octane 0.45
    formamide 191.87
    cyclopentanone 51.43
    2-pentanone 23.59
    anisole 13.77
    cyclopentyl methyl ether 16.93
    gamma-butyrolactone 71.52
    1-methoxy-2-propanol 105.02
    pyridine 14.57
    3-pentanone 21.18
    furfural 79.09
    n-dodecane 0.62
    diethylene glycol 106.29
    diisopropyl ether 4.28
    tert-amyl alcohol 22.55
    acetylacetone 41.78
    n-hexadecane 0.65
    acetophenone 19.92
    methyl propionate 35.53
    isopentyl acetate 9.85
    trichloroethylene 5.82
    n-nonanol 10.35
    cyclohexanol 9.61
    benzyl alcohol 15.3
    2-ethylhexanol 5.98
    isooctanol 7.0
    dipropyl ether 9.82
    1,2-dichlorobenzene 2.38
    ethyl lactate 39.54
    propylene carbonate 36.05
    n-methylformamide 243.31
    2-pentanol 10.12
    n-pentane 0.69
    1-propoxy-2-propanol 36.41
    1-methoxy-2-propyl acetate 26.17
    2-(2-methoxypropoxy) propanol 56.58
    mesitylene 2.09
    ε-caprolactone 26.57
    p-cymene 2.38
    epichlorohydrin 38.76
    1,1,1-trichloroethane 3.18
    2-aminoethanol 109.78
    morpholine-4-carbaldehyde 236.8
    sulfolane 116.13
    2,2,4-trimethylpentane 0.6
    2-methyltetrahydrofuran 22.0
    n-hexyl acetate 14.73
    isooctane 0.52
    2-(2-butoxyethoxy)ethanol 58.82
    sec-butyl acetate 10.96
    tert-butyl acetate 16.15
    decalin 0.63
    glycerin 205.61
    diglyme 106.97
    acrylic acid 75.1
    isopropyl myristate 7.8
    n-butyric acid 26.42
    acetyl acetate 16.18
    di(2-ethylhexyl) phthalate 13.73
    ethyl propionate 19.53
    nitromethane 263.24
    1,2-diethoxyethane 18.52
    benzonitrile 11.61
    trioctyl phosphate 9.69
    1-bromopropane 1.88
    gamma-valerolactone 104.65
    n-decanol 8.3
    triethyl phosphate 11.03
    4-methyl-2-pentanol 8.21
    propionitrile 28.78
    vinylene carbonate 36.53
    1,1,2-trichlorotrifluoroethane 71.44
    DMS 26.59
    cumene 2.2
    2-octanol 5.53
    2-hexanone 22.24
    octyl acetate 11.38
    limonene 3.22
    1,2-dimethoxyethane 116.62
    ethyl orthosilicate 9.25
    tributyl phosphate 11.36
    diacetone alcohol 40.2
    N,N-dimethylaniline 17.71
    acrylonitrile 53.22
    aniline 7.0
    1,3-propanediol 68.46
    bromobenzene 0.79
    dibromomethane 1.54
    1,1,2,2-tetrachloroethane 6.54
    2-methyl-cyclohexyl acetate 10.94
    tetrabutyl urea 22.05
    diisobutyl methanol 4.81
    2-phenylethanol 10.92
    styrene 1.66
    dioctyl adipate 17.77
    dimethyl sulfate 128.78
    ethyl butyrate 13.17
    methyl lactate 81.3
    butyl lactate 20.71
    diethyl carbonate 12.06
    propanediol butyl ether 57.64
    triethyl orthoformate 11.81
    p-tert-butyltoluene 2.45
    methyl 4-tert-butylbenzoate 27.15
    morpholine 64.51
    tert-butylamine 15.52
    n-dodecanol 6.67
    dimethoxymethane 147.02
    ethylene carbonate 27.2
    cyrene 72.38
    2-ethoxyethyl acetate 18.74
    2-ethylhexyl acetate 7.12
    1,2,4-trichlorobenzene 3.77
    4-methylpyridine 15.69
    dibutyl ether 7.32
    2,6-dimethyl-4-heptanol 4.81
    DEF 59.24
    dimethyl isosorbide 62.46
    tetrachloroethylene 4.21
    eugenol 35.9
    triacetin 34.96
    span 80 38.34
    1,4-butanediol 48.82
    1,1-dichloroethane 3.27
    2-methyl-1-pentanol 11.47
    methyl formate 182.58
    2-methyl-1-butanol 13.95
    n-decane 0.79
    butyronitrile 18.02
    3,7-dimethyl-1-octanol 8.78
    1-chlorooctane 2.43
    1-chlorotetradecane 1.62
    n-nonane 0.69
    undecane 0.68
    tert-butylcyclohexane 0.79
    cyclooctane 0.27
    cyclopentanol 20.03
    tetrahydropyran 13.94
    tert-amyl methyl ether 13.24
    2,5,8-trioxanonane 90.57
    1-hexene 2.34
    2-isopropoxyethanol 50.85
    2,2,2-trifluoroethanol 84.22
    methyl butyrate 26.73

    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