Phenylacetonitrile

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  • Identifiers

    CAS number
    140-29-4

    Molecular formula
    C8H7N

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1136.67
    • Carbowax: 1894.0

  • Odor profile

    Floral 66.73%
    Sweet 46.13%
    Spicy 37.4%
    Green 34.9%
    Rose 31.7%
    Balsamic 29.97%
    Cinnamon 28.21%
    Honey 28.17%
    Hyacinth 28.14%
    Geranium 27.85%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    117.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • -10.8 °F (EPA, 1998)
    • -23.8 °C

    Boiling point

    • 451.4 °F at 760 mmHg (EPA, 1998)
    • 233.5 °C
    • 233.00 to 234.00 °C. @ 760.00 mm Hg

    Flash point est.
    92.47 ˚C

    Flash point expt.

    • 215 °F (NTP, 1992)
    • 102 °C
    • 102 °C (closed cup)
    • 235 °F (113 °C) (Open cup)

    Solubility expt.

    • less than 1 mg/mL at 63 °F (NTP, 1992)
    • Miscible with oxygenated solvents.
    • SOL IN ALL PROP IN ALC, ETHER; SOL IN ACETONE
    • In water, 100 mg/L at 25 °C
    • 0.1 mg/mL at 25 °C

  • Synonyms

    • Phenylacetonitrile
    • Benzeneacetonitrile
    • 2-Phenylacetonitrile
    • BENZYL CYANIDE
    • 140-29-4
    • alpha-Tolunitrile
    • Benzyl nitrile
    • alpha-Cyanotoluene
    • (Cyanomethyl)benzene
    • Phenyl acetyl nitrile
    • Benzylnitrile
    • Acetonitrile, phenyl-
    • benzylcyanide
    • Benzylkyanid
    • Phenyl-acetonitrile
    • USAF KF-21
    • Toluene, alpha-cyano-
    • Acetic acid, phenyl-nitrile
    • 2-phenylethanenitrile
    • .omega.-Cyanotoluene
    • CCRIS 4698
    • NSC 118418
    • Phenacetonitrile
    • HSDB 2103
    • Phenylacetonitrile, liquid
    • omega-Cyanotoluene
    • EINECS 205-410-5
    • .alpha.-Tolunitrile
    • UNII-23G40PRP93
    • .alpha.-Cyanotoluene
    • 2-phenyl-acetonitrile
    • DTXSID2021492
    • AI3-04975
    • 23G40PRP93
    • Toluene, .alpha.-cyano-
    • NSC-118418
    • BENZYL CYANIDE-13C
    • DTXCID401492
    • CHEBI:25979
    • BENZYL-ALPHA-13C CYANIDE
    • EC 205-410-5
    • PHENYLACETONITRILE-2,2-D2
    • MFCD00001894
    • BENZYL-D7 CYANIDE, 98 ATOM % D
    • WLN: NC1R
    • Benzylkyanid [Czech]
    • TRIAMTERENE IMPURITY D (EP IMPURITY)
    • TRIAMTERENE IMPURITY D [EP IMPURITY]
    • UN2470
    • enzylcyanide
    • phenylacetonitile
    • phenylacteonitrile
    • Cyanophenylmethane
    • alpha -cyano-
    • alpha -tolunitrile
    • phenyl acetonitrile
    • BnCN
    • alpha -cyanotoluene
    • benzene acetonitrile
    • benzene-acetonitrile
    • alpha-Cyano-Toluene
    • Benzeneacetonitrile-d5
    • alpha-phenylacetonitrile
    • Benzyl cyanide, 98%
    • Toluene, alpha -cyano-
    • Benzeneacetonitrile, 9CI
    • Benzyl cyanide, >=99%
    • Phenylacetonitrile, liquid [UN2470] [Poison]
    • BENZYL CYANIDE [MI]
    • SCHEMBL37831
    • BENZYL CYANIDE [HSDB]
    • laquo Omegaraquo -cyanotoluene
    • CHEMBL3560735
    • NSC3407
    • Benzyl cyanide, analytical standard
    • NSC-3407
    • Phenylacetonitrile (Benzyl Cyanide)
    • QCA53826
    • VCA02636
    • Tox21_200217
    • NSC118418
    • STL199233
    • AKOS000118943
    • UN 2470
    • NCGC00090854-01
    • NCGC00090854-02
    • NCGC00257771-01
    • CAS-140-29-4
    • DB-004016
    • NS00009919
    • P0128
    • Phenylacetonitrile, liquid [UN2470] [Poison]
    • A807640
    • Q425620
    • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H
    • 205-410-5

  • Applications

    Phenylacetonitrile (CAS 140-29-4) is a versatile organic intermediate used to build arylacetic side chains in pharmaceuticals (a precursor to phenylacetic acid and related side chains for penicillins and other APIs), agrochemicals (intermediate for pyrethroid insecticides and certain herbicides/growth regulators), flavors and fragrances (converted to phenylacetaldehyde, phenylacetic acid, phenethyl alcohol, and related esters for jasmine/rose notes), and fine chemicals/materials (precursors to dyes, functional intermediates, and polymer additives); it is also employed as a semiochemical in pest monitoring/control traps (e.g., for spotted wing drosophila) and as a model substrate in catalysis research, leveraging the nitrile group for hydrolysis to acids/amides, reduction to amines/aldehydes, benzylic alkylation, and C–C bond-forming condensations to access diverse heterocycles and arylacetic frameworks.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 589.42
    methanol 740.04
    isopropanol 316.3
    water 5.21
    ethyl acetate 2651.02
    n-propanol 429.07
    acetone 4103.5
    n-butanol 267.22
    acetonitrile 2278.94
    DMF 4258.58
    toluene 452.43
    isobutanol 231.23
    1,4-dioxane 2963.84
    methyl acetate 2385.19
    THF 2592.21
    2-butanone 2158.34
    n-pentanol 171.13
    sec-butanol 233.46
    n-hexane 45.28
    ethylene glycol 349.51
    NMP 2575.68
    cyclohexane 165.92
    DMSO 4658.62
    n-butyl acetate 707.9
    n-octanol 125.79
    chloroform 2534.21
    n-propyl acetate 722.07
    acetic acid 1197.37
    dichloromethane 3161.33
    cyclohexanone 2220.01
    propylene glycol 266.51
    isopropyl acetate 808.38
    DMAc 2009.41
    2-ethoxyethanol 440.4
    isopentanol 177.56
    n-heptane 67.92
    ethyl formate 1042.52
    1,2-dichloroethane 2520.63
    n-hexanol 250.31
    2-methoxyethanol 1150.87
    isobutyl acetate 315.94
    tetrachloromethane 308.09
    n-pentyl acetate 290.55
    transcutol 2219.13
    n-heptanol 105.48
    ethylbenzene 161.51
    MIBK 465.06
    2-propoxyethanol 567.63
    tert-butanol 308.64
    MTBE 394.6
    2-butoxyethanol 274.32
    propionic acid 1043.77
    o-xylene 188.44
    formic acid 506.68
    diethyl ether 1094.07
    m-xylene 203.92
    p-xylene 201.96
    chlorobenzene 879.02
    dimethyl carbonate 1299.77
    n-octane 22.04
    formamide 1241.56
    cyclopentanone 3375.38
    2-pentanone 1425.68
    anisole 560.22
    cyclopentyl methyl ether 924.27
    gamma-butyrolactone 3940.52
    1-methoxy-2-propanol 694.74
    pyridine 2138.46
    3-pentanone 1506.8
    furfural 2090.24
    n-dodecane 20.29
    diethylene glycol 586.32
    diisopropyl ether 206.56
    tert-amyl alcohol 191.23
    acetylacetone 2250.96
    n-hexadecane 24.3
    acetophenone 473.78
    methyl propionate 2197.0
    isopentyl acetate 433.22
    trichloroethylene 3920.56
    n-nonanol 111.93
    cyclohexanol 332.43
    benzyl alcohol 255.49
    2-ethylhexanol 147.79
    isooctanol 81.7
    dipropyl ether 443.25
    1,2-dichlorobenzene 675.13
    ethyl lactate 276.61
    propylene carbonate 1513.47
    n-methylformamide 2073.75
    2-pentanol 177.01
    n-pentane 40.99
    1-propoxy-2-propanol 387.61
    1-methoxy-2-propyl acetate 738.11
    2-(2-methoxypropoxy) propanol 300.01
    mesitylene 117.36
    ε-caprolactone 1436.95
    p-cymene 95.79
    epichlorohydrin 2884.46
    1,1,1-trichloroethane 1542.75
    2-aminoethanol 352.8
    morpholine-4-carbaldehyde 2230.08
    sulfolane 3193.52
    2,2,4-trimethylpentane 16.09
    2-methyltetrahydrofuran 1536.41
    n-hexyl acetate 413.07
    isooctane 14.61
    2-(2-butoxyethoxy)ethanol 454.67
    sec-butyl acetate 369.05
    tert-butyl acetate 590.43
    decalin 49.13
    glycerin 411.81
    diglyme 1221.89
    acrylic acid 1086.9
    isopropyl myristate 159.74
    n-butyric acid 944.42
    acetyl acetate 1578.45
    di(2-ethylhexyl) phthalate 132.14
    ethyl propionate 826.06
    nitromethane 4958.98
    1,2-diethoxyethane 722.27
    benzonitrile 560.4
    trioctyl phosphate 101.13
    1-bromopropane 766.72
    gamma-valerolactone 3055.55
    n-decanol 88.11
    triethyl phosphate 189.86
    4-methyl-2-pentanol 89.41
    propionitrile 1062.7
    vinylene carbonate 1380.68
    1,1,2-trichlorotrifluoroethane 1454.4
    DMS 867.02
    cumene 85.12
    2-octanol 68.68
    2-hexanone 587.82
    octyl acetate 206.1
    limonene 171.02
    1,2-dimethoxyethane 1119.57
    ethyl orthosilicate 162.57
    tributyl phosphate 136.51
    diacetone alcohol 527.2
    N,N-dimethylaniline 245.14
    acrylonitrile 1552.96
    aniline 474.76
    1,3-propanediol 420.05
    bromobenzene 942.84
    dibromomethane 1628.3
    1,1,2,2-tetrachloroethane 2476.19
    2-methyl-cyclohexyl acetate 263.73
    tetrabutyl urea 191.58
    diisobutyl methanol 98.68
    2-phenylethanol 264.01
    styrene 283.46
    dioctyl adipate 263.58
    dimethyl sulfate 1870.86
    ethyl butyrate 556.2
    methyl lactate 683.68
    butyl lactate 212.62
    diethyl carbonate 378.34
    propanediol butyl ether 275.83
    triethyl orthoformate 298.42
    p-tert-butyltoluene 91.65
    methyl 4-tert-butylbenzoate 311.75
    morpholine 2363.74
    tert-butylamine 163.16
    n-dodecanol 70.68
    dimethoxymethane 2050.98
    ethylene carbonate 1246.74
    cyrene 305.71
    2-ethoxyethyl acetate 614.85
    2-ethylhexyl acetate 341.52
    1,2,4-trichlorobenzene 720.1
    4-methylpyridine 1215.35
    dibutyl ether 261.16
    2,6-dimethyl-4-heptanol 98.68
    DEF 1501.53
    dimethyl isosorbide 580.91
    tetrachloroethylene 1484.04
    eugenol 272.39
    triacetin 599.57
    span 80 248.46
    1,4-butanediol 148.89
    1,1-dichloroethane 1756.08
    2-methyl-1-pentanol 123.53
    methyl formate 1920.7
    2-methyl-1-butanol 161.6
    n-decane 30.96
    butyronitrile 665.54
    3,7-dimethyl-1-octanol 116.98
    1-chlorooctane 128.17
    1-chlorotetradecane 58.18
    n-nonane 30.69
    undecane 24.79
    tert-butylcyclohexane 32.38
    cyclooctane 47.07
    cyclopentanol 529.6
    tetrahydropyran 2002.64
    tert-amyl methyl ether 251.22
    2,5,8-trioxanonane 731.83
    1-hexene 162.46
    2-isopropoxyethanol 274.99
    2,2,2-trifluoroethanol 578.47
    methyl butyrate 892.18

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition / Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 See notebox Category 7A
Rinse-off products applied to the hair with some hand contact
 See notebox
Category 2
Products applied to the axillae
 See notebox Category 7B
Leave-on products applied to the hair with some hand contact
 See notebox
Category 3
Products applied to the face/body using fingertips
 See notebox Category 8
Products with significant anogenital exposure
 See notebox
Category 4
Products related to fine fragrance
 See notebox Category 9
Products with body and hand exposure, primarily rinse off
 See notebox
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 See notebox Category 10A
Household care products with mostly hand contact
 See notebox
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 See notebox Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 See notebox
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 See notebox Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 See notebox
Category 5D
Baby Creams, baby Oils and baby talc
 See notebox Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 See notebox
Category 6
Products with oral and lip exposure
 See notebox Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 See notebox

Prohibition
Benzyl cyanide as such should not be used as fragrance ingredient.
The natural extracts containing Benzyl cyanide should not be used as substitutes for this substance.

Restriction
On the basis of established maximum concentration levels of this substance in commercially available natural sources (like essential oils and extracts), exposure to this substance from the use of these oils and extracts is not significant and the use of these oils is authorized as long as the level of Benzyl cyanide in the finished product does not exceed 0.01% (100 ppm).

Botanical

Name CAS Botanical Proportion
Genet headspace 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 5.2%
False acacia headspace (Black locust) Robinia pseudoacacia L. (False acacia) (Black locust), fam. Leguminosae 2.5%
Genet absolute 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.23%
Honeysuckle headspace Lonicera caprifoleum L., fam. Caprifoliaceae 0.1%
Michelia champaca flower absolute Michelia champaca L., fam. Magnoliaceae 1.3%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.03%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.69%
Narcissus poeticus absolute 8023-75-4 Narcissus poeticus L., fam. Amaryllidaceae 0.1%
Mustard, flowers 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 3.0%
Mustard, leaves & stems 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 1.1%
Mustard, root 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 0.05%
Mustard seed (China) 1 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 0.97%
Daylily, Headspace Living Flower 2 Hemerocallis, ssp. Satin Glass, fam. Liliaceae 18.42%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 0.02%
Artemisia macrocephala (China) Artemisia macrocephala Jacq. ex Bess., fam. Asteraceae (Compositae) 2.99%
Genet headspace 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 2.0%
Hedychium coronarium flower headspace (China) Hedychium coronarium Koenig, fam. Zingiberaceae 0.37%
Aglaia duperreana flower (China) Aglaia duperreana Pierre, fam. Meliaceae 0.2%
Lily-of-the-valley flower headspace Convallaria majalis L., fam. Liliaceae (Convallariaceae) 3.04%
Jasmine polyanthum flower headspace Jasminum polyanthum L., fam. Oleaceae 3.36%
Jasmine azoricum concrete Jasminum azoricum L., fam. Oleaceae 0.7%
Jasmine sambac (France) concrete Jasminum sambac (L.) Aiton, fam. Oleaceae 2.7%
Acacia confusa flower (China) Acacia confusa Merr., fam. Mimosaceae (Leguminosae) 0.11%
Lemon flower headspace (clone ZH) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 17.6%
Narcissus tazetta (var. chinensis) 8023-75-4 Narcissus tazetta L., var. chinensis, fam. Amaryllidaceae 0.18%
Narcissus tazetta (var. chinensis) headspace 8023-75-4 Narcissus tazetta L., var. chinensis, fam. Amarillidaceae 0.01%
Neroli bigarade (bitter orange flower) Morocco 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.67%
Bitter orange flower water absolute 2 8030-28-2 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 2.5%
Bitter orange flower absolute 2 8030-28-2 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.7%
Tulip sylvestre Tulipa sylvestris L., fam. Liliaceae 0.69%
Premna serratifolia flower bud Premna serratifolia L. (P.obtusifolia Br.R., P.taitensis Sch.),Verbenaceae 0.1%
Couroupita guianensis flower (Brazil) Couroupita guainensis Auble., fam. Lecythidaceae 0.6%
Mullilam leaf (India) Zanthoxylum rhetsa D.C. syn. Z. limonella (Dennst.) Alston, fam. Rutaceae 0.01%
Shadberry fruit Amelanchier arborea Nutt., fam. Rosaceae 0.1%
Salvadora persica root Salvadora persica L., fam. Salvadoraceae 0.4%
Parsnip flower, headspace 90082-39-6 Pastinaca sativa L., fam. Apiaceae (Umbelliferae) 0.05%
Geneps fruit (Cuba) Melicocca bijuga L., fam. Sapindaceae 0.1%