Glycolonitrile

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  • Identifiers

    CAS number
    107-16-4

    Molecular formula
    C2H3NO

    SMILES
    C(C#N)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Floral 56.61%
    Sweet 26.37%
    Odorless 25.93%
    Fishy 19.86%
    Geranium 19.24%
    Bitter 18.07%
    Rose 16.71%
    Clean 16.58%
    Fresh 16.28%
    Oily 16.27%

     

    Flavor
    Bitter 53.61%
    Odorless 47.36%
    Mild 22.8%
    Formyl 19.44%
    Bland 19.18%
    Nitrile 19.03%
    Sweet-like 18.9%
    Mousy 18.74%
    Rotten 18.5%
    Very slight 18.14%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    5.56 (weak acid)

    Molecular weight
    57.05 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • Less than -98 °F (EPA, 1998)
    • less than -72 °C
    • -72 °C
    • <-98 °F

    Boiling point

    • 361 °F at 760 mmHg with slight decomposition (EPA, 1998)
    • 183 °C (slight decomp)
    • 183 °C
    • 361 °F (Decomposes)

    Flash point

    • 79.72 ˚C est.
    • greater than 200 °F (NTP, 1992)
    • Flash point > 200 °F

    Solubility expt.

    • greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
    • Very soluble in water, ethanol, and ethyl ether; insoluble in benzene.
    • Soluble in water, ethanol, and diethyl ether but insoluble in chloroform and benzene.
    • Solubility in water: good
    • Soluble

  • Synonyms

    • GLYCOLONITRILE
    • Hydroxyacetonitrile
    • 2-Hydroxyacetonitrile
    • 107-16-4
    • Cyanomethanol
    • Glycolic nitrile
    • Formaldehyde cyanohydrin
    • Glycollonitrile
    • Acetonitrile, hydroxy-
    • Hydroxyactonitrile
    • Glyconitrile
    • Hydroxymethylnitrile
    • 2-Hydroxyethanenitrile
    • Methylene cyanohydrin
    • Glykolonitril
    • Hydroxymethylkyanid
    • Acetonitrile, 2-hydroxy-
    • USAF A-8565
    • NSC 1790
    • HOCH2CN
    • CCRIS 4655
    • HSDB 2123
    • EINECS 203-469-1
    • UNII-ZCI474BE63
    • BRN 0605328
    • AI3-23958
    • NSC-1790
    • GLYCOLONITRILE [HSDB]
    • ZCI474BE63
    • DTXSID3025417
    • CHEBI:137685
    • 4-03-00-00598 (Beilstein Handbook Reference)
    • Glykolonitril [Czech]
    • alpha-Hydroxymethylcyanide
    • Hydroxyazetonitril
    • Glycolonitrile (ca. 52% in Water, ca. 9.7mol/L) (stabilized with H2SO4)
    • Hydroxyazetonitril [German]
    • Hydroxymethylkyanid [Czech]
    • cyanomethyl alcohol
    • 2Hydroxyacetonitrile
    • hydroxyl-acetonitrile
    • 2Hydroxyethanenitrile
    • Acetonitrile, hydroxy
    • 2-hydroxymethylnitrile
    • 2-oxidanylethanenitrile
    • Formaldehyde Cyanhydrin
    • cyanohydrin formaldehyde
    • Glycolonitrile (8CI)
    • alphaHydroxymethylcyanide
    • Formaldehyde, cyanohydrin
    • WLN: Q1CN
    • HYDROXYMETHYL CYANIDE
    • DTXCID405417
    • NSC1790
    • GLYCOLONITRILE in 50% Water
    • .ALPHA.-HYDROXYMETHYLCYANIDE
    • Glycolonitrile, 55 wt. % in H2O
    • MFCD00042731
    • AKOS015914931
    • BP-10057
    • H0191
    • NS00023444
    • Q25807
    • A801598
    • Glycolonitrile (Solution in Water) (Stabilized with H2SO4) >90%

  • Applications

    Glycolonitrile (CAS 107-16-4) is primarily used as an industrial intermediate; it serves as a precursor to glycolic acid (via hydrolysis), enabling the production of glycolate esters and derivatives used in cosmetics and household cleaners. It also provides a versatile entry point for cyanohydrin chemistry to access hydroxy carbonyl compounds and related fine chemicals. The compound is used as a building block in the synthesis of pharmaceutical and specialty chemical intermediates. In polymer chemistry, glycolonitrile supports routes to glycolic acid–derived polymers, including biodegradable polyesters. Additionally, it can function as a convenient nitrile source for the preparation of functionalized molecules in organic synthesis. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 58.54
    methanol 189.39
    isopropanol 23.05
    water 366.74
    ethyl acetate 11.32
    n-propanol 25.42
    acetone 62.68
    n-butanol 18.64
    acetonitrile 45.44
    DMF 350.01
    toluene 1.57
    isobutanol 13.6
    1,4-dioxane 32.08
    methyl acetate 23.16
    THF 29.95
    2-butanone 21.21
    n-pentanol 12.16
    sec-butanol 13.33
    n-hexane 0.57
    ethylene glycol 115.42
    NMP 220.48
    cyclohexane 1.48
    DMSO 539.24
    n-butyl acetate 10.92
    n-octanol 7.2
    chloroform 10.21
    n-propyl acetate 9.23
    acetic acid 288.47
    dichloromethane 17.95
    cyclohexanone 31.31
    propylene glycol 45.5
    isopropyl acetate 6.36
    DMAc 200.09
    2-ethoxyethanol 52.27
    isopentanol 12.16
    n-heptane 1.44
    ethyl formate 37.0
    1,2-dichloroethane 14.3
    n-hexanol 9.25
    2-methoxyethanol 111.23
    isobutyl acetate 4.35
    tetrachloromethane 3.02
    n-pentyl acetate 8.51
    transcutol 101.77
    n-heptanol 6.79
    ethylbenzene 1.15
    MIBK 6.25
    2-propoxyethanol 31.82
    tert-butanol 20.33
    MTBE 7.04
    2-butoxyethanol 24.11
    propionic acid 66.86
    o-xylene 2.55
    formic acid 512.6
    diethyl ether 6.43
    m-xylene 1.49
    p-xylene 2.01
    chlorobenzene 4.58
    dimethyl carbonate 14.21
    n-octane 0.64
    formamide 510.88
    cyclopentanone 39.05
    2-pentanone 12.33
    anisole 6.06
    cyclopentyl methyl ether 8.37
    gamma-butyrolactone 64.06
    1-methoxy-2-propanol 45.98
    pyridine 27.6
    3-pentanone 9.44
    furfural 117.56
    n-dodecane 0.58
    diethylene glycol 66.35
    diisopropyl ether 1.79
    tert-amyl alcohol 14.25
    acetylacetone 25.99
    n-hexadecane 0.59
    acetophenone 11.69
    methyl propionate 14.51
    isopentyl acetate 8.29
    trichloroethylene 21.44
    n-nonanol 6.02
    cyclohexanol 14.34
    benzyl alcohol 13.15
    2-ethylhexanol 5.68
    isooctanol 5.4
    dipropyl ether 6.33
    1,2-dichlorobenzene 6.54
    ethyl lactate 15.31
    propylene carbonate 30.0
    n-methylformamide 204.8
    2-pentanol 7.83
    n-pentane 0.85
    1-propoxy-2-propanol 21.63
    1-methoxy-2-propyl acetate 13.43
    2-(2-methoxypropoxy) propanol 26.73
    mesitylene 1.51
    ε-caprolactone 29.59
    p-cymene 2.78
    epichlorohydrin 34.75
    1,1,1-trichloroethane 5.2
    2-aminoethanol 85.01
    morpholine-4-carbaldehyde 172.33
    sulfolane 137.55
    2,2,4-trimethylpentane 0.61
    2-methyltetrahydrofuran 16.21
    n-hexyl acetate 9.55
    isooctane 0.38
    2-(2-butoxyethoxy)ethanol 33.87
    sec-butyl acetate 4.07
    tert-butyl acetate 6.82
    decalin 0.62
    glycerin 114.46
    diglyme 79.2
    acrylic acid 119.28
    isopropyl myristate 4.09
    n-butyric acid 48.25
    acetyl acetate 13.61
    di(2-ethylhexyl) phthalate 8.67
    ethyl propionate 6.57
    nitromethane 351.94
    1,2-diethoxyethane 15.57
    benzonitrile 14.95
    trioctyl phosphate 6.37
    1-bromopropane 3.94
    gamma-valerolactone 86.15
    n-decanol 4.65
    triethyl phosphate 7.47
    4-methyl-2-pentanol 4.35
    propionitrile 15.84
    vinylene carbonate 39.15
    1,1,2-trichlorotrifluoroethane 82.38
    DMS 12.21
    cumene 1.38
    2-octanol 4.13
    2-hexanone 8.7
    octyl acetate 6.4
    limonene 4.47
    1,2-dimethoxyethane 57.08
    ethyl orthosilicate 6.26
    tributyl phosphate 7.57
    diacetone alcohol 19.45
    N,N-dimethylaniline 8.43
    acrylonitrile 39.39
    aniline 10.05
    1,3-propanediol 73.26
    bromobenzene 2.87
    dibromomethane 9.0
    1,1,2,2-tetrachloroethane 18.11
    2-methyl-cyclohexyl acetate 7.46
    tetrabutyl urea 13.89
    diisobutyl methanol 4.25
    2-phenylethanol 10.2
    styrene 1.88
    dioctyl adipate 9.91
    dimethyl sulfate 48.97
    ethyl butyrate 9.9
    methyl lactate 31.81
    butyl lactate 15.93
    diethyl carbonate 7.75
    propanediol butyl ether 31.63
    triethyl orthoformate 8.78
    p-tert-butyltoluene 2.57
    methyl 4-tert-butylbenzoate 17.06
    morpholine 43.31
    tert-butylamine 8.74
    n-dodecanol 3.85
    dimethoxymethane 41.18
    ethylene carbonate 25.53
    cyrene 32.06
    2-ethoxyethyl acetate 14.71
    2-ethylhexyl acetate 6.0
    1,2,4-trichlorobenzene 8.25
    4-methylpyridine 18.2
    dibutyl ether 5.34
    2,6-dimethyl-4-heptanol 4.25
    DEF 42.62
    dimethyl isosorbide 35.08
    tetrachloroethylene 18.86
    eugenol 21.9
    triacetin 20.05
    span 80 23.27
    1,4-butanediol 37.27
    1,1-dichloroethane 6.2
    2-methyl-1-pentanol 8.3
    methyl formate 132.31
    2-methyl-1-butanol 11.72
    n-decane 0.74
    butyronitrile 14.57
    3,7-dimethyl-1-octanol 6.13
    1-chlorooctane 2.22
    1-chlorotetradecane 1.23
    n-nonane 0.72
    undecane 0.63
    tert-butylcyclohexane 0.54
    cyclooctane 0.55
    cyclopentanol 19.48
    tetrahydropyran 12.66
    tert-amyl methyl ether 5.72
    2,5,8-trioxanonane 57.47
    1-hexene 1.52
    2-isopropoxyethanol 23.86
    2,2,2-trifluoroethanol 135.06
    methyl butyrate 13.54

    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