Mandelonitrile

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  • Identifiers

    CAS number
    532-28-5

    Molecular formula
    C8H7NO

    SMILES
    C1=CC=C(C=C1)C(C#N)O

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 49.66%
    Floral 48.01%
    Spicy 38.68%
    Bitter 36.29%
    Almond 34.06%
    Balsamic 29.54%
    Powdery 26.41%
    Cinnamon 24.03%
    Vanilla 22.79%
    Aromatic 22.78%

     

    Flavor
    Bitter 62.82%
    Odorless 38.71%
    Mild 28.13%
    Nitrile 21.31%
    Sweet-like 19.96%
    Orange flower 19.02%
    Very strong 18.83%
    Indole 18.44%
    Urine 18.37%
    Orange blossom 18.31%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    6.33 (neutral)

    Molecular weight
    133.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 14 °F (also given as 72 °F) (NTP, 1992)
    • 21.5 - 22 °C

    Boiling point

    • 338 °F at 760 mmHg (decomposes) (NTP, 1992)

    Flash point

    • 115.39 ˚C est.
    • 179.5 °F (NTP, 1992)

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)

  • Synonyms

    • Mandelonitrile
    • 532-28-5
    • Benzaldehyde cyanohydrin
    • 2-hydroxy-2-phenylacetonitrile
    • Phenylglycolonitrile
    • Mandelic acid nitrile
    • Amygdalonitrile
    • ALPHA-HYDROXYBENZENEACETONITRILE
    • Glycolonitrile, phenyl-
    • Benzaldehydkyanhydrin
    • Mandelonitrile, tech grade
    • Acetonitrile, hydroxyphenyl-
    • Nitril kyseliny mandlove
    • hydroxy(phenyl)acetonitrile
    • Benzaldehyde, cyanohydrin
    • Mandelonitrile, (+-)-
    • Benzaldehydkyanhydrin [Czech]
    • NSC 77668
    • Benzeneacetonitrile, .alpha.-hydroxy-
    • CCRIS 4656
    • (+/-)-Mandelonitrile
    • Nitril kyseliny mandlove [Czech]
    • EINECS 208-532-7
    • (+-)-alpha-Hydroxybenzeneacetonitrile
    • BRN 2207122
    • DTXSID2025422
    • CHEBI:16910
    • AI3-50437
    • .alpha.-Hydroxybenzeneacetonitrile
    • UNII-584322E08A
    • Benzeneacetonitrile, alpha-hydroxy-
    • NSC-77668
    • (.+/-.)-Mandelonitrile
    • MANDELONITRILE [MI]
    • DTXCID705422
    • MANDELONITRILE [WHO-DD]
    • 584322E08A
    • 4-10-00-00578 (Beilstein Handbook Reference)
    • MANDELONITRILE DL-FORM [MI]
    • (+/-)-.ALPHA.-MANDELONITRILE
    • BENZENEACETONITRILE, .ALPHA.-HYDROXY-)
    • DL-MANDELONITRILE
    • MFCD00004487
    • alpha-Hydroxyphenylacetonitrile
    • 2-hydroxy-2-phenyl-acetonitrile
    • a-Hydroxy-benzeneacetonitrile; Benzaldehyde cyanohydrin; alpha-Hydroxyphenylacetonitrile
    • hydroxybenzyl cyanide
    • a-cyanobenzyl alcohol
    • racemic mandelonitrile
    • Glycolonitrile, phenyl
    • alphaCyanobenzyl alcohol
    • alpha-Cyanobenzyl alcohol
    • WLN: QYR&CN
    • 2Hydroxy2phenylacetonitrile
    • a-hydroxybenzeneacetonitrile
    • Acetonitrile, hydroxyphenyl
    • hydroxyl(phenyl)acetonitrile
    • .alpha.-Cyanobenzyl alcohol
    • alphaHydroxyphenylacetonitrile
    • NCIOpen2_000888
    • (+-)-MANDELONITRILE
    • alphaHydroxybenzeneacetonitrile
    • MANDELONITRILE DL-FORM
    • 613-88-7
    • SCHEMBL196731
    • Mandelonitrile, technical grade
    • 2-hydroxyl-2-phenylacetonitrile
    • Benzeneacetonitrile, alphahydroxy
    • CHEMBL1393845
    • (.+-.)-MANDELONITRILE
    • NSC77668
    • (+/-)-ALPHA-MANDELONITRILE
    • Tox21_200804
    • BBL100015
    • STL164354
    • AKOS005363772
    • FM02701
    • SB44716
    • SB45998
    • (+/-)-2-Hydroxy-2-phenylacetonitrile
    • NCGC00090867-01
    • NCGC00090867-02
    • NCGC00258358-01
    • CAS-532-28-5
    • SY102139
    • BENZENEACETONITRILE, ALPHA-HYDROXY-)
    • DB-058327
    • CS-0195943
    • M0566
    • NS00032684
    • A11559
    • Q3844407
    • 208-532-7

  • Applications

    Mandelonitrile is widely used as an intermediate to synthesize mandelic acid and mandelate derivatives, providing a key chiral building block for pharmaceutical and cosmetic applications. It also serves as a cyanohydrin precursor for the production of aroma- and flavor-related compounds, and as a feedstock for mandelate esters and amides used in fine-chemical manufacturing. In addition, mandelonitrile is evaluated for generating mandelic acid–based building blocks in asymmetric synthesis and pharmaceutical intermediates. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 203.54
    methanol 288.3
    isopropanol 128.47
    water 12.7
    ethyl acetate 321.91
    n-propanol 140.22
    acetone 841.24
    n-butanol 80.64
    acetonitrile 482.37
    DMF 1163.39
    toluene 51.62
    isobutanol 77.57
    1,4-dioxane 588.07
    methyl acetate 422.5
    THF 630.69
    2-butanone 389.4
    n-pentanol 59.71
    sec-butanol 79.71
    n-hexane 5.17
    ethylene glycol 201.43
    NMP 731.57
    cyclohexane 14.39
    DMSO 2077.5
    n-butyl acetate 141.86
    n-octanol 59.32
    chloroform 325.32
    n-propyl acetate 175.88
    acetic acid 424.61
    dichloromethane 354.52
    cyclohexanone 405.81
    propylene glycol 105.62
    isopropyl acetate 145.59
    DMAc 600.46
    2-ethoxyethanol 177.8
    isopentanol 55.88
    n-heptane 11.24
    ethyl formate 205.19
    1,2-dichloroethane 344.34
    n-hexanol 81.74
    2-methoxyethanol 348.87
    isobutyl acetate 90.56
    tetrachloromethane 49.52
    n-pentyl acetate 87.08
    transcutol 670.81
    n-heptanol 53.58
    ethylbenzene 30.18
    MIBK 118.28
    2-propoxyethanol 186.22
    tert-butanol 136.23
    MTBE 102.5
    2-butoxyethanol 117.39
    propionic acid 297.1
    o-xylene 40.09
    formic acid 255.51
    diethyl ether 150.87
    m-xylene 38.06
    p-xylene 41.34
    chlorobenzene 124.16
    dimethyl carbonate 226.69
    n-octane 6.35
    formamide 534.38
    cyclopentanone 732.71
    2-pentanone 259.9
    anisole 107.69
    cyclopentyl methyl ether 170.98
    gamma-butyrolactone 893.78
    1-methoxy-2-propanol 221.34
    pyridine 382.8
    3-pentanone 197.99
    furfural 480.33
    n-dodecane 6.95
    diethylene glycol 223.25
    diisopropyl ether 40.06
    tert-amyl alcohol 81.87
    acetylacetone 413.41
    n-hexadecane 7.81
    acetophenone 128.11
    methyl propionate 287.28
    isopentyl acetate 100.37
    trichloroethylene 534.7
    n-nonanol 53.13
    cyclohexanol 82.53
    benzyl alcohol 81.54
    2-ethylhexanol 47.31
    isooctanol 44.25
    dipropyl ether 78.75
    1,2-dichlorobenzene 109.7
    ethyl lactate 93.71
    propylene carbonate 366.73
    n-methylformamide 602.25
    2-pentanol 51.24
    n-pentane 5.27
    1-propoxy-2-propanol 124.02
    1-methoxy-2-propyl acetate 152.17
    2-(2-methoxypropoxy) propanol 122.7
    mesitylene 29.39
    ε-caprolactone 301.42
    p-cymene 28.27
    epichlorohydrin 601.62
    1,1,1-trichloroethane 204.97
    2-aminoethanol 162.93
    morpholine-4-carbaldehyde 564.08
    sulfolane 956.81
    2,2,4-trimethylpentane 4.47
    2-methyltetrahydrofuran 315.23
    n-hexyl acetate 120.17
    isooctane 4.75
    2-(2-butoxyethoxy)ethanol 173.97
    sec-butyl acetate 92.37
    tert-butyl acetate 145.5
    decalin 8.39
    glycerin 204.36
    diglyme 409.86
    acrylic acid 327.15
    isopropyl myristate 53.01
    n-butyric acid 217.6
    acetyl acetate 217.88
    di(2-ethylhexyl) phthalate 47.17
    ethyl propionate 136.64
    nitromethane 1230.65
    1,2-diethoxyethane 163.63
    benzonitrile 140.81
    trioctyl phosphate 42.23
    1-bromopropane 90.92
    gamma-valerolactone 637.87
    n-decanol 41.94
    triethyl phosphate 54.93
    4-methyl-2-pentanol 33.37
    propionitrile 208.71
    vinylene carbonate 301.43
    1,1,2-trichlorotrifluoroethane 404.1
    DMS 165.36
    cumene 24.07
    2-octanol 36.19
    2-hexanone 151.52
    octyl acetate 69.08
    limonene 40.25
    1,2-dimethoxyethane 313.14
    ethyl orthosilicate 48.84
    tributyl phosphate 46.25
    diacetone alcohol 177.71
    N,N-dimethylaniline 70.73
    acrylonitrile 338.37
    aniline 94.35
    1,3-propanediol 172.34
    bromobenzene 108.95
    dibromomethane 202.32
    1,1,2,2-tetrachloroethane 384.27
    2-methyl-cyclohexyl acetate 75.93
    tetrabutyl urea 71.09
    diisobutyl methanol 34.41
    2-phenylethanol 81.74
    styrene 42.99
    dioctyl adipate 80.75
    dimethyl sulfate 449.89
    ethyl butyrate 106.8
    methyl lactate 172.85
    butyl lactate 75.89
    diethyl carbonate 77.05
    propanediol butyl ether 119.06
    triethyl orthoformate 69.79
    p-tert-butyltoluene 28.37
    methyl 4-tert-butylbenzoate 114.79
    morpholine 491.54
    tert-butylamine 58.32
    n-dodecanol 33.95
    dimethoxymethane 450.85
    ethylene carbonate 253.53
    cyrene 132.56
    2-ethoxyethyl acetate 144.47
    2-ethylhexyl acetate 76.77
    1,2,4-trichlorobenzene 128.13
    4-methylpyridine 207.69
    dibutyl ether 64.84
    2,6-dimethyl-4-heptanol 34.41
    DEF 279.25
    dimethyl isosorbide 204.91
    tetrachloroethylene 253.06
    eugenol 107.66
    triacetin 163.26
    span 80 93.25
    1,4-butanediol 76.06
    1,1-dichloroethane 246.05
    2-methyl-1-pentanol 43.82
    methyl formate 505.01
    2-methyl-1-butanol 50.87
    n-decane 9.97
    butyronitrile 133.46
    3,7-dimethyl-1-octanol 45.97
    1-chlorooctane 39.21
    1-chlorotetradecane 18.64
    n-nonane 8.95
    undecane 8.17
    tert-butylcyclohexane 7.72
    cyclooctane 5.39
    cyclopentanol 151.18
    tetrahydropyran 356.65
    tert-amyl methyl ether 69.01
    2,5,8-trioxanonane 279.34
    1-hexene 21.6
    2-isopropoxyethanol 117.11
    2,2,2-trifluoroethanol 218.95
    methyl butyrate 192.93

    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