2-Chloroacetophenone

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  • Identifiers

    CAS number
    532-27-4

    Molecular formula
    C8H7ClO

    SMILES
    C1=CC=C(C=C1)C(=O)CCl

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 62.61%
    Balsamic 44.41%
    Honey 40.95%
    Floral 40.54%
    Vanilla 38.9%
    Spicy 37.32%
    Caramellic 35.71%
    Creamy 33.82%
    Powdery 33.49%
    Almond 33.06%

     

    Flavor
    Odorless 30.78%
    Mild 28.84%
    Nutty 25.73%
    Bitter 24.9%
    Faint 23.62%
    Honey 22.82%
    Balsam 22.46%
    Phenolic 22.4%
    Urine 22.01%
    Orange flower 21.11%

     

    Odor impact est.
    Medium

    Odor threshold

    • Odor Threshold Low: 0.01 [mmHg]. Odor threshold from NJ "Hazardous Substance Fact Sheet"
    • 0.1 mg/cu m
    • Odor low: 0.1020 mg/cu m; Odor high: 0.15 mg/cu m /Alphachloroacetophenone/

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    5.98 (weak acid)

    Molecular weight
    154.59 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 133.7 °F (NTP, 1992)
    • 56.5 °C
    • 54-59 °C
    • 134 °F

    Boiling point

    • 441 to 442 °F at 760 mmHg (NTP, 1992)
    • 247 °C
    • 244-245 °C
    • 472 °F

    Flash point

    • 99.79 ˚C est.
    • 244 °F (NTP, 1992)
    • 244 °F
    • 118 °C (closed cup)
    • 244 °F (118 °C) (Closed cup)
    • 118 °C c.c.

    Solubility expt.

    • less than 1 mg/mL at 66 °F (NTP, 1992)
    • Practically insoluble in water
    • Very soluble in ethanol, ethyl ether, benzene; soluble in acetone, petroleum ether
    • Soluble in carbon disulfide
    • Solubility in water, g/100ml at 25 °C: 1.64
    • Insoluble

  • Synonyms

    • 2-CHLOROACETOPHENONE
    • 532-27-4
    • Phenacyl chloride
    • 2-Chloro-1-phenylethanone
    • omega-Chloroacetophenone
    • CHLOROACETOPHENONE
    • alpha-Chloroacetophenone
    • Tear Gas
    • Mace (lacrimator)
    • Chloromethyl phenyl ketone
    • Ethanone, 2-chloro-1-phenyl-
    • Phenacylchloride
    • Chemical mace
    • Mace
    • 1-Chloroacetophenone
    • Acetophenone, 2-chloro-
    • CN (lacrimator)
    • Chloracetophenone
    • Phenyl chloromethyl ketone
    • NCI-C55107
    • 2-Chloro-1-phenylethan-1-one
    • .alpha.-Chloroacetophenone
    • 2-Chloroacetophenone (CN)
    • 2-Chloro-1-phenyl-ethanone
    • MFCD00000933
    • NSC 41666
    • .alpha.-Phenacyl chloride
    • .omega.-Chloroacetophenone
    • CHEMBL105712
    • DTXSID9020293
    • 88B5039IQG
    • NSC-41666
    • a-Chloroacetophenone
    • DTXCID90293
    • Phenylchloromethylketone
    • Caswell No. 179C
    • CAS-532-27-4
    • ?-Chloroacetophenone
    • CCRIS 2370
    • HSDB 972
    • Chloroacetophenone, 2-
    • EINECS 208-531-1
    • EPA Pesticide Chemical Code 018001
    • BRN 0507950
    • Benzeneacetaldehyde, a-chloro-
    • UNII-88B5039IQG
    • AI3-52322
    • Nutmeg fat
    • Nutmeg oleoresin
    • minyak bunga pala
    • minyak phuli pala
    • 2-chloroacetophenon
    • Chloroacetyl benzene
    • mace oil east indian
    • Benzoylmethyl chloride
    • 2-chloro acetophenone
    • 2-chloro-acetophenone
    • I+/--chloroacetophenone
    • mace indonesia oil fg 5
    • UNII-9KKX6I0U7Z
    • WLN: G1VR
    • 2-Chloroacetophenone, 98%
    • 9KKX6I0U7Z
    • SCHEMBL55444
    • 4-07-00-00641 (Beilstein Handbook Reference)
    • Chloroacetophenone (CN), solid [UN1697] [Poison]
    • (2-Chloro-1-oxoethyl)benzene
    • FEMA No. 2652
    • FEMA No. 2653
    • FEMA No. 2654
    • 1-Phenyl-2-chloro-1-ethanone
    • BDBM7873
    • Chloroacetophenone (CN), solid
    • GTPL6285
    • PHENYL CHLOROMETHYLKETONE
    • Chloroacetophenone (CN), liquid
    • HSDB 1950
    • Mace (Myristica fragrans Houtt.)
    • CHLOROACETOPHENONE [MART.]
    • NCI-C56484
    • NSC41666
    • STR01480
    • Halomethyl Phenyl Ketone deriv. 21
    • Tox21_202075
    • Tox21_300045
    • NM-003
    • AKOS000200777
    • OMEGA-CHLOROACETOPHENONE [HSDB]
    • UN 1697
    • .OMEGA.-CHLOROACETOPHENONE [MI]
    • NCGC00091207-01
    • NCGC00091207-02
    • NCGC00091207-03
    • NCGC00091207-04
    • NCGC00091207-05
    • NCGC00254035-01
    • NCGC00259624-01
    • DB-013352
    • NS00020661
    • 2-Chloroacetophenone, purum, >=98.0% (GC)
    • Q284209
    • Chloroacetophenone (CN), liquid [UN1697] [Poison]
    • Z57834468

  • Applications

    Chemical name 2-Chloroacetophenone (CAS 532-27-4) is primarily recognized as the tear gas agent CN, used as an irritant in riot-control formulations. It also functions as a versatile organic synthesis intermediate, enabling substitutions at the alpha-chloroacetyl moiety to access a range of acetophenone derivatives that serve as intermediates for pharmaceuticals and other specialty chemicals. In the fragrance and flavor sector, it is evaluated as a building block for aroma compounds. In research and industrial settings, it is used as a precursor for dye- and polymer-related intermediates. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 436.0
    methanol 437.81
    isopropanol 315.98
    water 8.6
    ethyl acetate 654.28
    n-propanol 319.92
    acetone 1346.33
    n-butanol 271.44
    acetonitrile 1002.57
    DMF 1549.62
    toluene 356.97
    isobutanol 249.69
    1,4-dioxane 1145.93
    methyl acetate 810.77
    THF 817.44
    2-butanone 780.47
    n-pentanol 236.16
    sec-butanol 260.83
    n-hexane 86.83
    ethylene glycol 174.47
    NMP 979.79
    cyclohexane 139.85
    DMSO 1487.78
    n-butyl acetate 386.63
    n-octanol 199.0
    chloroform 2053.08
    n-propyl acetate 503.94
    acetic acid 635.95
    dichloromethane 2152.76
    cyclohexanone 919.79
    propylene glycol 111.96
    isopropyl acetate 321.05
    DMAc 842.58
    2-ethoxyethanol 412.48
    isopentanol 241.26
    n-heptane 73.32
    ethyl formate 439.33
    1,2-dichloroethane 1534.8
    n-hexanol 240.01
    2-methoxyethanol 557.07
    isobutyl acetate 273.85
    tetrachloromethane 371.11
    n-pentyl acetate 276.74
    transcutol 1794.79
    n-heptanol 154.51
    ethylbenzene 246.52
    MIBK 305.68
    2-propoxyethanol 386.91
    tert-butanol 356.81
    MTBE 345.27
    2-butoxyethanol 290.97
    propionic acid 408.37
    o-xylene 242.56
    formic acid 229.96
    diethyl ether 541.53
    m-xylene 237.22
    p-xylene 296.36
    chlorobenzene 541.33
    dimethyl carbonate 309.28
    n-octane 37.81
    formamide 564.98
    cyclopentanone 1008.28
    2-pentanone 580.16
    anisole 469.76
    cyclopentyl methyl ether 439.13
    gamma-butyrolactone 1027.42
    1-methoxy-2-propanol 385.34
    pyridine 1054.28
    3-pentanone 465.61
    furfural 867.41
    n-dodecane 29.78
    diethylene glycol 372.97
    diisopropyl ether 153.17
    tert-amyl alcohol 276.21
    acetylacetone 672.87
    n-hexadecane 34.75
    acetophenone 441.19
    methyl propionate 488.02
    isopentyl acetate 305.19
    trichloroethylene 2444.78
    n-nonanol 163.6
    cyclohexanol 338.93
    benzyl alcohol 311.28
    2-ethylhexanol 169.49
    isooctanol 134.44
    dipropyl ether 276.82
    1,2-dichlorobenzene 488.35
    ethyl lactate 182.64
    propylene carbonate 539.16
    n-methylformamide 683.39
    2-pentanol 207.14
    n-pentane 69.44
    1-propoxy-2-propanol 282.66
    1-methoxy-2-propyl acetate 316.51
    2-(2-methoxypropoxy) propanol 287.77
    mesitylene 156.03
    ε-caprolactone 686.26
    p-cymene 126.87
    epichlorohydrin 1164.81
    1,1,1-trichloroethane 1130.3
    2-aminoethanol 231.98
    morpholine-4-carbaldehyde 956.51
    sulfolane 1082.25
    2,2,4-trimethylpentane 34.73
    2-methyltetrahydrofuran 681.47
    n-hexyl acetate 379.44
    isooctane 30.17
    2-(2-butoxyethoxy)ethanol 416.62
    sec-butyl acetate 270.05
    tert-butyl acetate 310.04
    decalin 71.63
    glycerin 214.96
    diglyme 959.56
    acrylic acid 422.42
    isopropyl myristate 149.37
    n-butyric acid 463.38
    acetyl acetate 392.5
    di(2-ethylhexyl) phthalate 117.18
    ethyl propionate 371.19
    nitromethane 1406.47
    1,2-diethoxyethane 528.64
    benzonitrile 475.29
    trioctyl phosphate 93.73
    1-bromopropane 610.65
    gamma-valerolactone 990.99
    n-decanol 121.8
    triethyl phosphate 149.69
    4-methyl-2-pentanol 131.72
    propionitrile 539.16
    vinylene carbonate 537.32
    1,1,2-trichlorotrifluoroethane 730.91
    DMS 357.42
    cumene 151.38
    2-octanol 127.39
    2-hexanone 478.29
    octyl acetate 178.53
    limonene 178.58
    1,2-dimethoxyethane 813.75
    ethyl orthosilicate 146.87
    tributyl phosphate 118.79
    diacetone alcohol 339.68
    N,N-dimethylaniline 312.39
    acrylonitrile 767.32
    aniline 380.31
    1,3-propanediol 293.44
    bromobenzene 590.26
    dibromomethane 1353.1
    1,1,2,2-tetrachloroethane 1582.27
    2-methyl-cyclohexyl acetate 219.18
    tetrabutyl urea 174.67
    diisobutyl methanol 119.3
    2-phenylethanol 260.57
    styrene 341.74
    dioctyl adipate 203.08
    dimethyl sulfate 498.75
    ethyl butyrate 312.01
    methyl lactate 221.65
    butyl lactate 197.93
    diethyl carbonate 228.78
    propanediol butyl ether 284.57
    triethyl orthoformate 205.99
    p-tert-butyltoluene 117.33
    methyl 4-tert-butylbenzoate 299.61
    morpholine 998.02
    tert-butylamine 238.29
    n-dodecanol 95.29
    dimethoxymethane 633.71
    ethylene carbonate 430.34
    cyrene 269.48
    2-ethoxyethyl acetate 363.04
    2-ethylhexyl acetate 250.15
    1,2,4-trichlorobenzene 523.06
    4-methylpyridine 759.34
    dibutyl ether 280.26
    2,6-dimethyl-4-heptanol 119.3
    DEF 675.9
    dimethyl isosorbide 429.8
    tetrachloroethylene 1275.62
    eugenol 304.43
    triacetin 372.47
    span 80 235.88
    1,4-butanediol 157.43
    1,1-dichloroethane 1254.47
    2-methyl-1-pentanol 207.12
    methyl formate 603.36
    2-methyl-1-butanol 225.49
    n-decane 49.62
    butyronitrile 467.3
    3,7-dimethyl-1-octanol 160.13
    1-chlorooctane 181.81
    1-chlorotetradecane 71.51
    n-nonane 53.38
    undecane 37.31
    tert-butylcyclohexane 61.31
    cyclooctane 48.45
    cyclopentanol 356.56
    tetrahydropyran 855.66
    tert-amyl methyl ether 257.34
    2,5,8-trioxanonane 591.7
    1-hexene 252.96
    2-isopropoxyethanol 305.32
    2,2,2-trifluoroethanol 295.46
    methyl butyrate 521.58

    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