Perchloromethyl mercaptan

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  • Identifiers

    CAS number
    594-42-3

    Molecular formula
    CCl4S

    SMILES
    C(SCl)(Cl)(Cl)Cl

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sulfurous 38.63%
    Meaty 33.62%
    Sweet 27.74%
    Green 27.24%
    Savory 26.89%
    Grapefruit 26.61%
    Onion 25.86%
    Odorless 25.32%
    Tropical 24.98%
    Fresh 23.62%

     

    Flavor
    Sulfurous 36.13%
    Sulfury 29.26%
    Meaty 27.98%
    Odorless 27.38%
    Onion 24.4%
    Roasted 19.92%
    Glue 19.38%
    Bouillon 19.21%
    Bloody 19.15%
    Greasy 18.76%

     

    Odor impact est.
    Medium

    Odor threshold

    • Odor Threshold Low: 0.001 [mmHg]. Odor threshold from CHEMINFO

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    3.11 (weak acid)

    Molecular weight
    185.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point

    • 297 to 298 °F at 760 mmHg (EPA, 1998)
    • 147-148 °C @ 760 MM HG, 51 °C @ 25 MM HG
    • 147-148 °C
    • 297 °F
    • 297 °F (Decomposes)

    Flash point

    • 49.53 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • SOL IN ETHER; INSOL IN WATER
    • Solubility in water: none
    • Insoluble

  • Synonyms

    • Perchloromethyl mercaptan
    • 594-42-3
    • Clairsit
    • TRICHLOROMETHANESULFENYL CHLORIDE
    • Perchloromethylmercaptan
    • Methanesulfenyl chloride, trichloro-
    • Perchloromethanethiol
    • Trichloromethylsulfenyl chloride
    • Perchlormethylmerkaptan
    • (Trichloromethane)sulfenyl chloride
    • Perchlorinemethylmercaptan
    • Thiocarbonyl tetrachloride
    • RCRA waste number P118
    • Trichloromethanesulphenyl chloride
    • Trichloromethane sulfenyl chloride
    • Mercaptan methylique perchlore
    • Trichlormethyl sulfur chloride
    • trichloromethyl thiohypochlorite
    • Trichloromethylsulphenyl chloride
    • Trichloromethyl sulfochloride
    • NSC 66404
    • HSDB 886
    • Perchlormethylmerkaptan [Czech]
    • HSDB 6052
    • Perchloro-methyl-mercaptan (DOT)
    • Methanesulfenic acid, trichloro-, chloride
    • EINECS 209-840-4
    • KK489OII9M
    • UN1670
    • Mercaptan methylique perchlore [French]
    • BRN 0506034
    • DTXSID6025854
    • (Trichloromethyl)sulfenyl chloride
    • Perchloro-methyl-mercaptan
    • NSC-66404
    • DTXCID205854
    • EC 209-840-4
    • TRICHLOROMETHYLSULFANYL CHLORIDE
    • TRICHLOROMETHANESULFENYL CHLORIDE [HSDB]
    • PERCHLORMETHYLMERKAPTAN (CZECH)
    • Trichloromethyl sulfur chloride
    • MERCAPTAN METHYLIQUE PERCHLORE (FRENCH)
    • RCRA waste no. P118
    • UNII-KK489OII9M
    • Trichloromethyl sulphochloride
    • Trichloromethane sulphuryl chloride
    • MFCD00037054
    • perchlormethylmercaptan
    • Methanethiol, trichloro
    • WLN: GXGGSG
    • SCHEMBL190299
    • Perchloromethylmercaptan (DOT)
    • trichloromethyl sulfenyl chloride
    • CHEMBL3188766
    • RYFZYYUIAZYQLC-UHFFFAOYSA-
    • trichloro-methanesulfenyl chloride
    • trichloromethane-sulfenyl chloride
    • trichloro-methanesulphenyl chloride
    • trichloromethane sulphenyl chloride
    • Methanesulfenyl chloride, trichloro
    • NSC66404
    • Tox21_200422
    • trichloromethanesulphenic acid chloride
    • AKOS006222983
    • UN 1670
    • Perchloromethyl mercaptan (ACGIH:OSHA)
    • Methanesulfenic acid, trichloro, chloride
    • NCGC00248604-01
    • NCGC00257976-01
    • THRICHLOROMETHANESULPHENYL CHLORIDE
    • TRICHLOROMETHANE SULFURYL CHLORIDE
    • CAS-594-42-3
    • Trichloromethanesulfenyl chloride, >=96%
    • InChI=1/CCl4S/c2-1(3,4)6-5
    • DB-092501
    • NS00002483
    • P0740
    • Perchloromethyl mercaptan [UN1670] [Poison]
    • Q680191
    • 209-840-4

  • Applications

    Perchloromethyl mercaptan, CAS 594-42-3, is a highly reactive sulfur-containing chloromethylating agent used primarily as an intermediate in the synthesis of organosulfur compounds. In agriculture, it is commonly evaluated as a precursor for sulfur-containing pesticides and related crop-protection agents. In industrial manufacturing, it serves as a chloromethylating reagent to introduce chloromethyl functionality into thiol- or amine-containing substrates, enabling the preparation of specialty chemicals. In the polymers and plastics sector, it is used as a building block or functional monomer precursor and as a crosslinking or linking agent. In coatings and inks, it is used as a functional precursor for surface-functionalization and coating formulations. Due to its reactivity and toxicity, handling and compliance with local regulations are essential.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 52.36
    methanol 64.68
    isopropanol 39.75
    water 2.62
    ethyl acetate 53.25
    n-propanol 41.51
    acetone 117.14
    n-butanol 41.89
    acetonitrile 35.56
    DMF 362.48
    toluene 41.2
    isobutanol 31.7
    1,4-dioxane 115.52
    methyl acetate 61.51
    THF 255.78
    2-butanone 82.11
    n-pentanol 39.11
    sec-butanol 39.24
    n-hexane 10.2
    ethylene glycol 31.84
    NMP 346.62
    cyclohexane 22.39
    DMSO 374.19
    n-butyl acetate 64.04
    n-octanol 41.66
    chloroform 95.34
    n-propyl acetate 51.81
    acetic acid 70.31
    dichloromethane 94.18
    cyclohexanone 126.29
    propylene glycol 24.07
    isopropyl acetate 47.3
    DMAc 251.6
    2-ethoxyethanol 87.67
    isopentanol 37.77
    n-heptane 22.9
    ethyl formate 54.87
    1,2-dichloroethane 79.24
    n-hexanol 45.0
    2-methoxyethanol 129.71
    isobutyl acetate 33.78
    tetrachloromethane 28.15
    n-pentyl acetate 59.87
    transcutol 177.57
    n-heptanol 39.37
    ethylbenzene 27.34
    MIBK 54.94
    2-propoxyethanol 92.43
    tert-butanol 52.01
    MTBE 59.78
    2-butoxyethanol 70.13
    propionic acid 35.06
    o-xylene 41.17
    formic acid 48.21
    diethyl ether 64.33
    m-xylene 37.04
    p-xylene 33.37
    chlorobenzene 46.75
    dimethyl carbonate 52.07
    n-octane 12.08
    formamide 83.84
    cyclopentanone 176.88
    2-pentanone 78.9
    anisole 61.72
    cyclopentyl methyl ether 109.48
    gamma-butyrolactone 156.49
    1-methoxy-2-propanol 93.76
    pyridine 119.48
    3-pentanone 67.12
    furfural 182.09
    n-dodecane 8.61
    diethylene glycol 84.87
    diisopropyl ether 30.39
    tert-amyl alcohol 48.92
    acetylacetone 102.69
    n-hexadecane 9.54
    acetophenone 80.54
    methyl propionate 63.1
    isopentyl acetate 54.42
    trichloroethylene 129.85
    n-nonanol 39.83
    cyclohexanol 57.52
    benzyl alcohol 62.83
    2-ethylhexanol 40.49
    isooctanol 34.62
    dipropyl ether 61.4
    1,2-dichlorobenzene 47.81
    ethyl lactate 37.34
    propylene carbonate 75.54
    n-methylformamide 110.19
    2-pentanol 36.27
    n-pentane 15.93
    1-propoxy-2-propanol 79.73
    1-methoxy-2-propyl acetate 74.72
    2-(2-methoxypropoxy) propanol 74.53
    mesitylene 29.94
    ε-caprolactone 99.96
    p-cymene 36.93
    epichlorohydrin 152.04
    1,1,1-trichloroethane 56.65
    2-aminoethanol 37.9
    morpholine-4-carbaldehyde 255.97
    sulfolane 267.31
    2,2,4-trimethylpentane 9.47
    2-methyltetrahydrofuran 134.37
    n-hexyl acetate 60.75
    isooctane 7.7
    2-(2-butoxyethoxy)ethanol 94.45
    sec-butyl acetate 36.77
    tert-butyl acetate 59.79
    decalin 10.31
    glycerin 48.38
    diglyme 172.79
    acrylic acid 42.4
    isopropyl myristate 36.92
    n-butyric acid 47.66
    acetyl acetate 40.42
    di(2-ethylhexyl) phthalate 35.56
    ethyl propionate 44.39
    nitromethane 125.74
    1,2-diethoxyethane 82.56
    benzonitrile 62.0
    trioctyl phosphate 29.68
    1-bromopropane 48.58
    gamma-valerolactone 199.99
    n-decanol 32.85
    triethyl phosphate 35.7
    4-methyl-2-pentanol 28.16
    propionitrile 33.45
    vinylene carbonate 64.61
    1,1,2-trichlorotrifluoroethane 144.74
    DMS 49.92
    cumene 23.09
    2-octanol 34.7
    2-hexanone 61.36
    octyl acetate 43.32
    limonene 54.97
    1,2-dimethoxyethane 157.11
    ethyl orthosilicate 36.85
    tributyl phosphate 31.63
    diacetone alcohol 78.35
    N,N-dimethylaniline 77.87
    acrylonitrile 48.81
    aniline 62.79
    1,3-propanediol 49.08
    bromobenzene 39.59
    dibromomethane 68.61
    1,1,2,2-tetrachloroethane 112.83
    2-methyl-cyclohexyl acetate 50.29
    tetrabutyl urea 60.35
    diisobutyl methanol 35.62
    2-phenylethanol 64.51
    styrene 33.08
    dioctyl adipate 50.83
    dimethyl sulfate 103.42
    ethyl butyrate 57.5
    methyl lactate 52.32
    butyl lactate 49.98
    diethyl carbonate 36.12
    propanediol butyl ether 62.31
    triethyl orthoformate 49.27
    p-tert-butyltoluene 39.47
    methyl 4-tert-butylbenzoate 85.65
    morpholine 143.23
    tert-butylamine 39.12
    n-dodecanol 27.74
    dimethoxymethane 172.85
    ethylene carbonate 51.72
    cyrene 94.2
    2-ethoxyethyl acetate 72.63
    2-ethylhexyl acetate 48.87
    1,2,4-trichlorobenzene 63.14
    4-methylpyridine 112.01
    dibutyl ether 48.04
    2,6-dimethyl-4-heptanol 35.62
    DEF 133.59
    dimethyl isosorbide 142.03
    tetrachloroethylene 93.63
    eugenol 81.54
    triacetin 65.1
    span 80 67.15
    1,4-butanediol 29.81
    1,1-dichloroethane 55.78
    2-methyl-1-pentanol 34.38
    methyl formate 97.79
    2-methyl-1-butanol 36.33
    n-decane 13.12
    butyronitrile 37.45
    3,7-dimethyl-1-octanol 40.47
    1-chlorooctane 33.02
    1-chlorotetradecane 17.45
    n-nonane 13.13
    undecane 10.37
    tert-butylcyclohexane 10.12
    cyclooctane 11.96
    cyclopentanol 69.65
    tetrahydropyran 97.69
    tert-amyl methyl ether 63.25
    2,5,8-trioxanonane 138.71
    1-hexene 24.03
    2-isopropoxyethanol 66.11
    2,2,2-trifluoroethanol 39.49
    methyl butyrate 61.31

    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