2-Chlorobenzalmalononitrile

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  • Identifiers

    CAS number
    2698-41-1

    Molecular formula
    C10H5ClN2

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 47.35%
    Spicy 44.72%
    Sweet 36.89%
    Bitter 25.31%
    Powdery 21.19%
    Cinnamon 20.56%
    Balsamic 20.37%
    Citrus 19.79%
    Geranium 19.29%
    Dry 19.07%

     

    Flavor
    Bitter 83.42%
    Odorless 28.92%
    Nitrile 20.18%
    Very strong 17.09%
    Oriental 16.96%
    Rotten 16.65%
    Indole 16.62%
    Taco 16.43%
    Bread crust 16.34%
    Sweet-like 16.21%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    4.97 (weak acid)

    Molecular weight
    188.61 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 203 °F (NTP, 1992)
    • 95-96 °C
    • 93-96 °C
    • 203-205 °F

    Boiling point

    • 590 to 599 °F at 760 mmHg (NTP, 1992)
    • 310-315 °C
    • 590-599 °F

    Flash point

    • 156.01 ˚C est.

    Solubility expt.

    • 1 to 5 mg/mL at 61 °F (NTP, 1992)
    • Sparingly soluble in water
    • Soluble in acetone, dioxane, methylene chloride, ethyl acetate, benzene; sparingly soluble in water
    • Solubility in water, g/100ml at 20 °C: 0.1-0.5
    • Insoluble

  • Synonyms

    • 2698-41-1
    • 2-Chlorobenzylidenemalononitrile
    • [(2-Chlorophenyl)methylene]malononitrile
    • 2-(2-Chlorobenzylidene)malononitrile
    • Alonitrile
    • o-Chlorobenzylidenemalononitrile
    • CS (lacrimator)
    • o-Chlorobenzalmalononitrile
    • 2-CHLOROBENZALMALONONITRILE
    • o-Chlorobenzylidene malononitrile
    • 2-Chlorobmn
    • USAF KF-11
    • (o-Chlorobenzal)malononitrile
    • o-Chlorobenzylidenemalonic nitrile
    • (o-Chlorobenzylidene)malononitrile
    • NCI-C55118
    • 2-[(2-chlorophenyl)methylidene]propanedinitrile
    • 2-Chlorobenzylidene malononitrile
    • NSC 542
    • chlorobenzylidene malononitrile
    • o-Chlorobenzylidenemalonitrile
    • 2-Chlorobenzylidene malonitrile
    • Malononitrile, (o-chlorobenzylidene)-
    • o-Chlorobenzylidene malonitrile
    • CCRIS 2377
    • HSDB 4346
    • beta,beta-Dicyano-o-chlorostyrene
    • (2-Chlorobenzylidene)malononitrile
    • ortho-Chlorobenzylidene malononitrile
    • EINECS 220-278-9
    • (2-chlorobenzylidene)propanedinitrile
    • TL 238
    • Propanedinitrile, ((2-chlorophenyl)methylene)-
    • .beta.,.beta.-Dicyano-o-chlorostyrene
    • 2-Chloro BMN
    • BRN 1866635
    • D8317IAV7Q
    • ((2-Chloro-phenyl)methylene)propanenitrile
    • NSC-542
    • Malononitrile, o-chlorobenzylidene-
    • Propanedinitrile, ((2-chlorophenyl)methylene)
    • Propanedinitrile, [(2-chlorophenyl)methylene]-
    • ((2-Chlorophenyl)methylene)malononitrile
    • 2-Chlorobenzylidenemaloninitrile
    • (o-Chlorobenzylidene)malonitrile
    • CHEMBL1256101
    • 2-[(2-Chlorophenyl)methylene]propanedinitrile
    • CHLOROBENZALMALONITRILE, O-
    • NSC637336
    • 2-CHLOROBENZALMALONONITRILE [HSDB]
    • ((2-chlorophenyl)methylene)propanedinitrile
    • [(2-Chlorophenyl)methylene]propanedinitrile
    • O-CHLOROBENZYLIDENEMALONONITRILE [MI]
    • Propanedinitrile, 2-((2-chlorophenyl)methylene)-
    • Propanedinitrile, 2-[(2-chlorophenyl)methylene]-
    • 2-((2-CHLOROPHENYL)METHYLENE)PROPANEDINITRILE
    • CS GAS
    • o-Chlorobenzalmalonitrile
    • chlorobenzylidenemalononitrile
    • (2-(Chlorophenyl)methylene)malononitrile
    • [2-(Chlorophenyl)methylene]malononitrile
    • CS gas (lacrimator)
    • Propanedinitrile, [(2-chlorophenyl)methylene]
    • UNII-D8317IAV7Q
    • 2Chlorobmn
    • 2-CHLOROBENZALMALONITRILE
    • Propanedinitrile, [(chlorophenyl)methylene]-
    • CS Tear Gas
    • MFCD00019784
    • Tear Gas, CS
    • CS(LACRIMITOR)
    • 2Chlorobenzalmalononitrile
    • CS (riot control agent)
    • (oChlorobenzal)malononitrile
    • WLN: NCYCN&U1R BG
    • beta,betaDicyanoochlorostyrene
    • o Chlorobenzylidenemalonitrile
    • oChlorobenzylidene malonitrile
    • 2 Chlorobenzylidenemalonitrile
    • 2-Chlorobenzylidenemalonitrile
    • 2Chlorobenzylidene malonitrile
    • 2Chlorobenzylidenemalononitrile
    • SCHEMBL436060
    • o Chlorobenzylidene Malonitrile
    • o Chlorobenzylidene malonotrile
    • o-Chlorobenzylidene malonotrile
    • 2 Chlorobenzylidene Malonitrile
    • oChlorobenzylidene malononitrile
    • 2Chlorobenzylidene malononitrile
    • GTPL4158
    • NSC542
    • Malonitrile, o-Chlorobenzylidene
    • malonotrile, o-Chlorobenzylidene
    • oChlorobenzylidenemalonic nitrile
    • (oChlorobenzylidene)malononitrile
    • DTXSID9020297
    • Malonitrile, 2-Chlorobenzylidene
    • ortho Chlorobenzylidenemalonitrile
    • ortho-Chlorobenzylidenemalonitrile
    • CHEBI:188626
    • ortho-chlorobenzylidene malonitrile
    • beta,bbeta-Dicyano-o-chlorostyrene
    • ortho Chlorobenzylidene Malonitrile
    • orthochlorobenzylidene malononitrile
    • Malononitrile, (ochlorobenzylidene)
    • Malonitrile, ortho-Chlorobenzylidene
    • BDBM50327657
    • STL196772
    • AKOS000504237
    • NSC-637336
    • ((2Chlorophenyl)methylene)propanenitrile
    • 2-(2-Chlorobenzylidene)malononitrile #
    • AS-11303
    • SY106828
    • CS-0095253
    • NS00020621
    • Propanedinitrile, ((2chlorophenyl)methylene)
    • A18547
    • H11803
    • o-Chlorobenzylidene malononitrile (ACGIH:OSHA)
    • Q209357
    • [(2-chlorophenyl)methylene]malononitrile; ((2-chlorophenyl)methylene)propanedinitrile
    • 220-278-9

  • Applications

    2-Chlorobenzalmalononitrile (CAS 2698-41-1) is primarily used as a tear gas agent for crowd-control and public-safety applications, deployed in formulations and dispersal devices to induce tearing and irritation. It can also function as an intermediate in the synthesis of arylidene malononitrile derivatives used in specialty chemicals and material development. In safety and toxicology research, it is employed as a reference material for exposure assessment and analytical method development. Additionally, it is used in training and evaluation of protective equipment and procedures for handling irritants, subject to local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 30.6
    methanol 35.96
    isopropanol 20.1
    water 0.12
    ethyl acetate 371.85
    n-propanol 23.34
    acetone 845.49
    n-butanol 15.3
    acetonitrile 399.17
    DMF 1079.17
    toluene 230.47
    isobutanol 16.19
    1,4-dioxane 576.53
    methyl acetate 572.79
    THF 840.97
    2-butanone 539.26
    n-pentanol 18.74
    sec-butanol 21.31
    n-hexane 3.84
    ethylene glycol 27.85
    NMP 1817.91
    cyclohexane 14.59
    DMSO 1319.4
    n-butyl acetate 232.85
    n-octanol 21.38
    chloroform 669.25
    n-propyl acetate 219.4
    acetic acid 179.08
    dichloromethane 1021.78
    cyclohexanone 728.98
    propylene glycol 22.89
    isopropyl acetate 199.09
    DMAc 1037.89
    2-ethoxyethanol 91.7
    isopentanol 16.75
    n-heptane 7.34
    ethyl formate 191.71
    1,2-dichloroethane 716.93
    n-hexanol 29.82
    2-methoxyethanol 140.77
    isobutyl acetate 108.39
    tetrachloromethane 79.81
    n-pentyl acetate 130.31
    transcutol 720.98
    n-heptanol 17.83
    ethylbenzene 100.94
    MIBK 126.83
    2-propoxyethanol 101.64
    tert-butanol 30.69
    MTBE 90.15
    2-butoxyethanol 69.68
    propionic acid 118.47
    o-xylene 124.77
    formic acid 67.7
    diethyl ether 109.77
    m-xylene 104.93
    p-xylene 137.29
    chlorobenzene 444.29
    dimethyl carbonate 317.51
    n-octane 2.47
    formamide 268.07
    cyclopentanone 1383.92
    2-pentanone 268.47
    anisole 349.51
    cyclopentyl methyl ether 281.93
    gamma-butyrolactone 1466.79
    1-methoxy-2-propanol 88.59
    pyridine 913.31
    3-pentanone 315.24
    furfural 1311.94
    n-dodecane 2.36
    diethylene glycol 99.69
    diisopropyl ether 37.14
    tert-amyl alcohol 31.43
    acetylacetone 840.73
    n-hexadecane 3.04
    acetophenone 424.03
    methyl propionate 349.81
    isopentyl acetate 177.17
    trichloroethylene 2069.27
    n-nonanol 20.39
    cyclohexanol 40.94
    benzyl alcohol 139.97
    2-ethylhexanol 30.23
    isooctanol 15.89
    dipropyl ether 76.8
    1,2-dichlorobenzene 442.41
    ethyl lactate 84.57
    propylene carbonate 597.29
    n-methylformamide 373.68
    2-pentanol 13.39
    n-pentane 2.61
    1-propoxy-2-propanol 81.21
    1-methoxy-2-propyl acetate 294.99
    2-(2-methoxypropoxy) propanol 142.97
    mesitylene 57.54
    ε-caprolactone 517.69
    p-cymene 58.86
    epichlorohydrin 1353.89
    1,1,1-trichloroethane 578.24
    2-aminoethanol 27.45
    morpholine-4-carbaldehyde 1046.25
    sulfolane 1822.47
    2,2,4-trimethylpentane 3.27
    2-methyltetrahydrofuran 477.12
    n-hexyl acetate 166.27
    isooctane 2.15
    2-(2-butoxyethoxy)ethanol 154.33
    sec-butyl acetate 136.14
    tert-butyl acetate 226.29
    decalin 11.21
    glycerin 48.66
    diglyme 496.71
    acrylic acid 190.39
    isopropyl myristate 65.81
    n-butyric acid 83.86
    acetyl acetate 478.6
    di(2-ethylhexyl) phthalate 69.52
    ethyl propionate 202.85
    nitromethane 1483.47
    1,2-diethoxyethane 237.53
    benzonitrile 337.35
    trioctyl phosphate 38.66
    1-bromopropane 136.84
    gamma-valerolactone 1212.36
    n-decanol 15.7
    triethyl phosphate 97.89
    4-methyl-2-pentanol 11.68
    propionitrile 140.44
    vinylene carbonate 532.2
    1,1,2-trichlorotrifluoroethane 680.72
    DMS 447.71
    cumene 50.49
    2-octanol 13.74
    2-hexanone 204.39
    octyl acetate 84.8
    limonene 80.97
    1,2-dimethoxyethane 276.27
    ethyl orthosilicate 75.27
    tributyl phosphate 62.46
    diacetone alcohol 175.11
    N,N-dimethylaniline 167.8
    acrylonitrile 334.49
    aniline 189.42
    1,3-propanediol 32.4
    bromobenzene 556.67
    dibromomethane 433.08
    1,1,2,2-tetrachloroethane 973.85
    2-methyl-cyclohexyl acetate 145.64
    tetrabutyl urea 86.36
    diisobutyl methanol 21.89
    2-phenylethanol 126.2
    styrene 174.56
    dioctyl adipate 131.59
    dimethyl sulfate 761.12
    ethyl butyrate 178.48
    methyl lactate 152.86
    butyl lactate 89.2
    diethyl carbonate 143.57
    propanediol butyl ether 85.64
    triethyl orthoformate 112.13
    p-tert-butyltoluene 55.93
    methyl 4-tert-butylbenzoate 181.09
    morpholine 451.95
    tert-butylamine 17.23
    n-dodecanol 12.89
    dimethoxymethane 353.6
    ethylene carbonate 344.58
    cyrene 216.93
    2-ethoxyethyl acetate 324.13
    2-ethylhexyl acetate 154.69
    1,2,4-trichlorobenzene 591.33
    4-methylpyridine 698.72
    dibutyl ether 62.69
    2,6-dimethyl-4-heptanol 21.89
    DEF 376.22
    dimethyl isosorbide 412.54
    tetrachloroethylene 577.03
    eugenol 159.09
    triacetin 351.96
    span 80 97.33
    1,4-butanediol 19.73
    1,1-dichloroethane 422.83
    2-methyl-1-pentanol 20.52
    methyl formate 423.13
    2-methyl-1-butanol 16.38
    n-decane 3.65
    butyronitrile 79.99
    3,7-dimethyl-1-octanol 28.8
    1-chlorooctane 28.12
    1-chlorotetradecane 11.99
    n-nonane 3.36
    undecane 2.91
    tert-butylcyclohexane 7.48
    cyclooctane 5.07
    cyclopentanol 76.76
    tetrahydropyran 309.66
    tert-amyl methyl ether 75.92
    2,5,8-trioxanonane 309.55
    1-hexene 20.17
    2-isopropoxyethanol 71.26
    2,2,2-trifluoroethanol 138.22
    methyl butyrate 237.05

    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