1,2-Benzenedicarbonitrile

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  • Identifiers

    CAS number
    91-15-6

    Molecular formula
    C8H4N2

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

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Floral 38.27%
    Sweet 36.89%
    Bitter 30.74%
    Spicy 30.63%
    Almond 25.72%
    Powdery 21.19%
    Animal 20.99%
    Burnt 20.85%
    Phenolic 20.77%
    Odorless 20.34%

     

    Flavor
    Bitter 75.61%
    Odorless 27.1%
    Nitrile 21.04%
    Very strong 18.3%
    Indole 17.88%
    Rotten 17.46%
    Taco 17.27%
    Moth ball 16.96%
    Bread crust 16.96%
    Roasted peanuts 16.87%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    5.48 (weak acid)

    Molecular weight
    128.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 138 °C
    • 141 °C

    Boiling point

    • 304.5 °C

    Flash point

    • 135.1 ˚C est.
    • 162 °C

    Solubility expt.

    • Soluble in alcohol and ether
    • Soluble in acetone and benzene.
    • In water, 395 mg/l @ 25 °C.
    • Solubility in water, g/100ml at 25 °C: 0.06

  • Synonyms

    • Phthalonitrile
    • 1,2-Dicyanobenzene
    • 91-15-6
    • Phthalodinitrile
    • o-Phthalodinitrile
    • 1,2-BENZENEDICARBONITRILE
    • o-Dicyanobenzene
    • 1,2-Benzodinitrile
    • benzene-1,2-dicarbonitrile
    • o-Cyanobenzonitrile
    • o-Benzenedinitrile
    • o-Benzenedicarbonitrile
    • o-Pdn
    • Phthalic acid dinitrile
    • Ftalodinitril
    • Ftalonitril
    • USAF ND-09
    • ortho-Dicyanobenzene
    • Ftalonitril [Czech]
    • Ftalodinitril [Czech]
    • 1,2-Benzendikarbonitril
    • NSC 17562
    • CCRIS 8898
    • HSDB 5273
    • EINECS 202-044-8
    • 1,2-BIS(CYANO)BENZENE
    • DTXSID8029604
    • AI3-00049
    • 978627YAJU
    • NSC-17562
    • DTXCID709604
    • EC 202-044-8
    • 1,2-BENZENEDICARBONITRILE [HSDB]
    • O-PHTHALONITRILE
    • 1,2-Benzendikarbonitril [Czech]
    • oDicyanobenzene
    • UNII-978627YAJU
    • o-benzodinitrile
    • oBenzenedinitrile
    • oPhthalodinitrile
    • oCyanobenzonitrile
    • orthodicyanobenzene
    • 1,2Benzodinitrile
    • 1,2Dicyanobenzene
    • MFCD00001771
    • oBenzenedicarbonitrile
    • 1, 2-Dicyanobenzene
    • 1,2Benzendikarbonitril
    • WLN: NCR BCN
    • SCHEMBL57480
    • 1,2-Dicyanobenzene, 98%
    • PHTHALIC ACID, DINITRILE
    • CHEMBL3185350
    • CHEBI:232056
    • NSC17562
    • Tox21_200999
    • STK802328
    • AKOS000120698
    • CS-W016553
    • FP62498
    • CAS-91-15-6
    • NCGC00248893-01
    • NCGC00258552-01
    • AC-14597
    • DB-030219
    • NS00009417
    • P0404
    • EN300-21053
    • D70390
    • Q408783
    • F0001-2216
    • Z104486876
    • 202-044-8

  • Applications

    1,2-Benzenedicarbonitrile (CAS 91-15-6, ortho-dicyanobenzene) is primarily used as an organic synthesis intermediate, serving as a building block for aromatic nitrile derivatives and polycyclic compounds. It is commonly used as a precursor in the synthesis of pharmaceutical and agrochemical intermediates, and as a building block for heterocyclic compounds; it is also a feedstock for polymers and plastics, and a component for coatings and inks formulations. In addition, it may be evaluated for electronics-related specialty materials given its aryl nitrile character and the potential for tailoring to specific formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.78
    methanol 35.8
    isopropanol 13.79
    water 1.75
    ethyl acetate 112.51
    n-propanol 16.02
    acetone 220.13
    n-butanol 11.39
    acetonitrile 169.66
    DMF 872.14
    toluene 25.19
    isobutanol 9.87
    1,4-dioxane 195.82
    methyl acetate 187.24
    THF 206.77
    2-butanone 126.05
    n-pentanol 11.51
    sec-butanol 10.29
    n-hexane 3.97
    ethylene glycol 37.83
    NMP 520.18
    cyclohexane 7.83
    DMSO 384.05
    n-butyl acetate 63.97
    n-octanol 20.37
    chloroform 212.41
    n-propyl acetate 56.58
    acetic acid 71.38
    dichloromethane 205.76
    cyclohexanone 170.83
    propylene glycol 18.33
    isopropyl acetate 57.37
    DMAc 472.33
    2-ethoxyethanol 41.26
    isopentanol 9.96
    n-heptane 5.84
    ethyl formate 96.2
    1,2-dichloroethane 186.17
    n-hexanol 19.76
    2-methoxyethanol 92.99
    isobutyl acetate 33.02
    tetrachloromethane 40.22
    n-pentyl acetate 47.46
    transcutol 205.12
    n-heptanol 15.7
    ethylbenzene 21.19
    MIBK 41.47
    2-propoxyethanol 57.34
    tert-butanol 17.62
    MTBE 24.92
    2-butoxyethanol 41.67
    propionic acid 61.89
    o-xylene 22.11
    formic acid 43.45
    diethyl ether 40.55
    m-xylene 19.21
    p-xylene 31.56
    chlorobenzene 94.48
    dimethyl carbonate 170.22
    n-octane 4.37
    formamide 133.53
    cyclopentanone 308.38
    2-pentanone 79.03
    anisole 69.66
    cyclopentyl methyl ether 57.45
    gamma-butyrolactone 404.59
    1-methoxy-2-propanol 57.64
    pyridine 208.49
    3-pentanone 94.41
    furfural 366.73
    n-dodecane 4.13
    diethylene glycol 76.78
    diisopropyl ether 14.95
    tert-amyl alcohol 13.02
    acetylacetone 202.99
    n-hexadecane 4.96
    acetophenone 85.21
    methyl propionate 137.55
    isopentyl acetate 48.4
    trichloroethylene 380.48
    n-nonanol 19.19
    cyclohexanol 15.86
    benzyl alcohol 37.43
    2-ethylhexanol 17.34
    isooctanol 13.21
    dipropyl ether 29.89
    1,2-dichlorobenzene 104.45
    ethyl lactate 38.56
    propylene carbonate 180.9
    n-methylformamide 239.41
    2-pentanol 8.53
    n-pentane 2.42
    1-propoxy-2-propanol 41.79
    1-methoxy-2-propyl acetate 87.02
    2-(2-methoxypropoxy) propanol 57.4
    mesitylene 17.05
    ε-caprolactone 134.35
    p-cymene 18.3
    epichlorohydrin 275.6
    1,1,1-trichloroethane 146.39
    2-aminoethanol 28.13
    morpholine-4-carbaldehyde 332.84
    sulfolane 440.65
    2,2,4-trimethylpentane 1.89
    2-methyltetrahydrofuran 87.44
    n-hexyl acetate 64.82
    isooctane 1.94
    2-(2-butoxyethoxy)ethanol 65.95
    sec-butyl acetate 34.12
    tert-butyl acetate 59.8
    decalin 6.24
    glycerin 44.51
    diglyme 206.58
    acrylic acid 96.49
    isopropyl myristate 29.1
    n-butyric acid 48.68
    acetyl acetate 129.54
    di(2-ethylhexyl) phthalate 28.78
    ethyl propionate 61.44
    nitromethane 445.81
    1,2-diethoxyethane 71.96
    benzonitrile 91.14
    trioctyl phosphate 22.11
    1-bromopropane 43.3
    gamma-valerolactone 304.65
    n-decanol 15.32
    triethyl phosphate 38.75
    4-methyl-2-pentanol 7.96
    propionitrile 76.53
    vinylene carbonate 198.6
    1,1,2-trichlorotrifluoroethane 209.19
    DMS 151.16
    cumene 16.18
    2-octanol 12.66
    2-hexanone 53.66
    octyl acetate 35.92
    limonene 22.46
    1,2-dimethoxyethane 137.29
    ethyl orthosilicate 30.76
    tributyl phosphate 27.28
    diacetone alcohol 61.94
    N,N-dimethylaniline 48.53
    acrylonitrile 174.09
    aniline 41.77
    1,3-propanediol 28.43
    bromobenzene 97.47
    dibromomethane 112.38
    1,1,2,2-tetrachloroethane 262.8
    2-methyl-cyclohexyl acetate 40.52
    tetrabutyl urea 42.54
    diisobutyl methanol 14.43
    2-phenylethanol 41.76
    styrene 32.3
    dioctyl adipate 46.02
    dimethyl sulfate 334.35
    ethyl butyrate 50.75
    methyl lactate 86.72
    butyl lactate 38.46
    diethyl carbonate 49.25
    propanediol butyl ether 39.72
    triethyl orthoformate 39.15
    p-tert-butyltoluene 19.17
    methyl 4-tert-butylbenzoate 68.59
    morpholine 143.61
    tert-butylamine 10.47
    n-dodecanol 12.7
    dimethoxymethane 226.0
    ethylene carbonate 142.06
    cyrene 68.14
    2-ethoxyethyl acetate 83.65
    2-ethylhexyl acetate 42.69
    1,2,4-trichlorobenzene 123.41
    4-methylpyridine 132.55
    dibutyl ether 31.17
    2,6-dimethyl-4-heptanol 14.43
    DEF 155.46
    dimethyl isosorbide 116.57
    tetrachloroethylene 178.36
    eugenol 63.73
    triacetin 101.78
    span 80 40.63
    1,4-butanediol 16.37
    1,1-dichloroethane 109.19
    2-methyl-1-pentanol 10.5
    methyl formate 258.06
    2-methyl-1-butanol 8.39
    n-decane 6.33
    butyronitrile 46.22
    3,7-dimethyl-1-octanol 18.89
    1-chlorooctane 22.33
    1-chlorotetradecane 11.0
    n-nonane 6.17
    undecane 4.98
    tert-butylcyclohexane 5.07
    cyclooctane 3.43
    cyclopentanol 32.32
    tetrahydropyran 80.69
    tert-amyl methyl ether 22.11
    2,5,8-trioxanonane 133.17
    1-hexene 10.99
    2-isopropoxyethanol 28.71
    2,2,2-trifluoroethanol 72.95
    methyl butyrate 77.85

    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