Chloroacetyl chloride

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  • Identifiers

    CAS number
    79-04-9

    Molecular formula
    C2H2Cl2O

    SMILES
    C(C(=O)Cl)Cl

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 51.52%
    Sweet 30.54%
    Buttery 28.77%
    Fatty 27.02%
    Caramellic 25.85%
    Savory 22.29%
    Fishy 20.93%
    Milky 20.62%
    Creamy 20.61%
    Meaty 19.36%

     

    Flavor
    Odorless 49.71%
    Roasted 22.64%
    Mild 22.61%
    Cooked 22.18%
    Sulfury 22.08%
    Mousy 20.93%
    Bland 19.72%
    Sulfurous 19.5%
    Yeast 19.45%
    Taco 19.18%

     

    Odor impact est.
    High

    Odor threshold

    • An industrial hygienist was not able to detect odor at 0.011 ppm, found 0.023 ppm barely detectable, and 0.140 ppm "strong".

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    5.23 (weak acid)

    Molecular weight
    112.94 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -8.5 °F (USCG, 1999)
    • -21.7 °C
    • -21.8 °C
    • -8.5 °F
    • -7 °F

    Boiling point

    • 221 °F at 760 mmHg (USCG, 1999)
    • 106.0 °C
    • 106 °C
    • 223 °F

    Flash point

    • 47.65 ˚C est.
    • 100 °C (212 °F) - closed cup

    Solubility expt.

    • Decomposes (NIOSH, 2024)
    • Decomposed by water
    • Initially insoluble in water, however a slow reaction at the water-chloroacetyl chloride interface produces chloroacetic acid. When sufficient acid is formed to solubilize the two phases, a violent reaction forming chloroacetic acid and HCl occurs.
    • Miscible with ethyl ether; soluble in acetone, carbon tetrachloride.
    • Miscible with acetone and benzene.
    • Solubility in water: reaction
    • Decomposes

  • Synonyms

    • CHLOROACETYL CHLORIDE
    • 79-04-9
    • 2-chloroacetyl chloride
    • Acetyl chloride, chloro-
    • Chloracetyl chloride
    • Chloroacetic chloride
    • Monochloroacetyl chloride
    • ChloroacetylChloride
    • Chloroacetic acid chloride
    • Chloroethanoyl chloride
    • CCRIS 9145
    • HSDB 973
    • Chlorure de chloracetyle
    • UNII-K5UML06YUO
    • K5UML06YUO
    • chloracetylchloride
    • Chlorid kyseliny chloroctove
    • EINECS 201-171-6
    • Acetyl chloride, 2-chloro-
    • UN1752
    • .alpha.-Chloroacetyl chloride
    • CH2ClCOCl
    • BRN 0605439
    • chloro acetyl chloride
    • DTXSID4026472
    • MFCD00000725
    • alpha-Chloroacetyl chloride
    • monochloroacetic acid chloride
    • DTXCID306472
    • CHEBI:34624
    • EC 201-171-6
    • 4-02-00-00488 (Beilstein Handbook Reference)
    • CHLOROACETYL CHLORIDE [HSDB]
    • UN 1752
    • chloro-acetyl chloride
    • Chlorure de chloracetyle [French]
    • Chlorid kyseliny chloroctove [Czech]
    • chloroacetylchlonde
    • chloroacetylchoride
    • chloroactylchloride
    • Chloroacetylchlorid
    • chloro acetylchlorid
    • chloroacetyl choride
    • chloroactyl chloride
    • choroacetyl chloride
    • Chloroacetic Acid Chloride; Chloroacetic Chloride; Chloroethanoyl Chloride; Monochloroacetyl Chloride;
    • chioroacetyl chloride
    • chloro-acetylchloride
    • chloroacetyl-chloride
    • Chloro acetylchloride
    • ClCH2COCl
    • chloro-actyl chloride
    • chloroacethyl chloride
    • 2-chloroacetylchloride
    • chloroacetyl chloride-
    • a-chloroacetyl chloride
    • 2-chloro acetylchloride
    • 2-chloro-acetylchloride
    • 2-chloroacetic chloride
    • Acetyl chloride, chloro
    • alpha-chloroacetylchloride
    • 2-chloro-acetyl chloride
    • alpha-chloro-acetylchloride
    • 2-chloranylethanoyl chloride
    • SCHEMBL9584
    • 2-chloroacetic acid chloride
    • Chloroacetyl chloride, 98%
    • Chloroacetyl chloride (ACGIH)
    • CHEMBL3187685
    • CHLORACETYL CHLORIDE [MI]
    • BCP25293
    • Tox21_200644
    • BBL013127
    • STK399762
    • AKOS000121312
    • CAS-79-04-9
    • NCGC00248777-01
    • NCGC00258198-01
    • VS-03683
    • Chloroacetyl chloride [UN1752] [Poison]
    • NS00004813
    • EN300-19172
    • Chloroacetyl chloride, purum, >=99.0% (GC)
    • A839561
    • Q411258
    • F2190-0033
    • 201-171-6

  • Applications

    Chloroacetyl chloride is a highly reactive acyl chloride used as a selective acylating agent to install the chloroacetyl moiety onto amino, hydroxyl, or thiol groups to give N-chloroacetyl amides, O-chloroacetyl esters, or thioesters. In practice it is commonly employed as an intermediate in the synthesis of pharmaceutical and agrochemical building blocks, as well as in polymer and resin chemistry to functionalize polymers or prepare crosslinkable adhesives, coatings, and specialty materials. It can serve as a precursor for chloroacetyl derivatives used in further transformations in industrial manufacturing. Use is subject to proper handling and regulatory requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 215.36
    methanol 323.2
    isopropanol 169.89
    water 105.94
    ethyl acetate 168.57
    n-propanol 162.27
    acetone 630.07
    n-butanol 130.62
    acetonitrile 478.77
    DMF 1144.84
    toluene 90.0
    isobutanol 122.99
    1,4-dioxane 415.9
    methyl acetate 281.49
    THF 371.57
    2-butanone 323.12
    n-pentanol 119.33
    sec-butanol 147.38
    n-hexane 37.45
    ethylene glycol 138.95
    NMP 926.85
    cyclohexane 49.44
    DMSO 937.88
    n-butyl acetate 100.87
    n-octanol 81.72
    chloroform 196.79
    n-propyl acetate 146.16
    acetic acid 293.34
    dichloromethane 275.57
    cyclohexanone 310.05
    propylene glycol 88.08
    isopropyl acetate 99.08
    DMAc 1093.73
    2-ethoxyethanol 295.15
    isopentanol 107.54
    n-heptane 36.1
    ethyl formate 177.98
    1,2-dichloroethane 230.93
    n-hexanol 77.64
    2-methoxyethanol 415.94
    isobutyl acetate 82.28
    tetrachloromethane 47.59
    n-pentyl acetate 77.61
    transcutol 567.1
    n-heptanol 49.83
    ethylbenzene 68.88
    MIBK 116.91
    2-propoxyethanol 188.6
    tert-butanol 181.35
    MTBE 159.64
    2-butoxyethanol 116.05
    propionic acid 148.08
    o-xylene 108.5
    formic acid 224.65
    diethyl ether 204.18
    m-xylene 76.96
    p-xylene 99.32
    chlorobenzene 98.68
    dimethyl carbonate 145.07
    n-octane 16.98
    formamide 404.66
    cyclopentanone 341.15
    2-pentanone 205.57
    anisole 196.61
    cyclopentyl methyl ether 184.66
    gamma-butyrolactone 335.46
    1-methoxy-2-propanol 261.7
    pyridine 274.88
    3-pentanone 214.37
    furfural 424.71
    n-dodecane 15.01
    diethylene glycol 226.83
    diisopropyl ether 62.99
    tert-amyl alcohol 151.74
    acetylacetone 276.76
    n-hexadecane 16.23
    acetophenone 213.86
    methyl propionate 189.72
    isopentyl acetate 82.49
    trichloroethylene 310.72
    n-nonanol 73.83
    cyclohexanol 142.86
    benzyl alcohol 148.09
    2-ethylhexanol 63.16
    isooctanol 44.38
    dipropyl ether 118.56
    1,2-dichlorobenzene 103.56
    ethyl lactate 91.24
    propylene carbonate 153.87
    n-methylformamide 447.78
    2-pentanol 98.35
    n-pentane 40.92
    1-propoxy-2-propanol 131.05
    1-methoxy-2-propyl acetate 123.12
    2-(2-methoxypropoxy) propanol 188.1
    mesitylene 58.26
    ε-caprolactone 215.76
    p-cymene 52.8
    epichlorohydrin 311.45
    1,1,1-trichloroethane 140.77
    2-aminoethanol 157.92
    morpholine-4-carbaldehyde 815.31
    sulfolane 433.34
    2,2,4-trimethylpentane 20.66
    2-methyltetrahydrofuran 246.26
    n-hexyl acetate 109.6
    isooctane 11.88
    2-(2-butoxyethoxy)ethanol 210.15
    sec-butyl acetate 87.61
    tert-butyl acetate 102.66
    decalin 28.2
    glycerin 142.35
    diglyme 432.62
    acrylic acid 174.18
    isopropyl myristate 61.23
    n-butyric acid 122.7
    acetyl acetate 119.58
    di(2-ethylhexyl) phthalate 64.03
    ethyl propionate 136.34
    nitromethane 669.46
    1,2-diethoxyethane 206.19
    benzonitrile 173.85
    trioctyl phosphate 47.13
    1-bromopropane 127.5
    gamma-valerolactone 484.72
    n-decanol 60.08
    triethyl phosphate 76.58
    4-methyl-2-pentanol 55.91
    propionitrile 206.62
    vinylene carbonate 165.14
    1,1,2-trichlorotrifluoroethane 279.71
    DMS 136.53
    cumene 59.1
    2-octanol 44.45
    2-hexanone 175.72
    octyl acetate 73.72
    limonene 78.96
    1,2-dimethoxyethane 597.65
    ethyl orthosilicate 74.12
    tributyl phosphate 61.34
    diacetone alcohol 139.9
    N,N-dimethylaniline 202.55
    acrylonitrile 268.39
    aniline 136.14
    1,3-propanediol 159.33
    bromobenzene 84.52
    dibromomethane 174.67
    1,1,2,2-tetrachloroethane 227.25
    2-methyl-cyclohexyl acetate 88.39
    tetrabutyl urea 115.72
    diisobutyl methanol 50.14
    2-phenylethanol 91.22
    styrene 91.49
    dioctyl adipate 98.66
    dimethyl sulfate 265.84
    ethyl butyrate 108.19
    methyl lactate 127.63
    butyl lactate 77.11
    diethyl carbonate 83.69
    propanediol butyl ether 127.91
    triethyl orthoformate 93.48
    p-tert-butyltoluene 50.71
    methyl 4-tert-butylbenzoate 130.84
    morpholine 417.91
    tert-butylamine 123.62
    n-dodecanol 52.56
    dimethoxymethane 444.95
    ethylene carbonate 129.95
    cyrene 202.42
    2-ethoxyethyl acetate 123.57
    2-ethylhexyl acetate 73.77
    1,2,4-trichlorobenzene 135.95
    4-methylpyridine 282.86
    dibutyl ether 108.23
    2,6-dimethyl-4-heptanol 50.14
    DEF 384.05
    dimethyl isosorbide 240.88
    tetrachloroethylene 168.96
    eugenol 149.11
    triacetin 159.94
    span 80 134.88
    1,4-butanediol 105.7
    1,1-dichloroethane 164.06
    2-methyl-1-pentanol 104.2
    methyl formate 366.35
    2-methyl-1-butanol 112.99
    n-decane 22.68
    butyronitrile 164.91
    3,7-dimethyl-1-octanol 73.5
    1-chlorooctane 55.82
    1-chlorotetradecane 30.21
    n-nonane 23.16
    undecane 17.63
    tert-butylcyclohexane 23.3
    cyclooctane 21.46
    cyclopentanol 150.95
    tetrahydropyran 237.55
    tert-amyl methyl ether 150.58
    2,5,8-trioxanonane 337.22
    1-hexene 81.37
    2-isopropoxyethanol 190.45
    2,2,2-trifluoroethanol 183.93
    methyl butyrate 179.68

    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