Bis(Chloromethyl) Ether

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  • Identifiers

    CAS number
    542-88-1

    Molecular formula
    C2H4Cl2O

    SMILES
    C(OCCl)Cl

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Alcoholic 44.58%
    Fruity 43.35%
    Ethereal 41.44%
    Odorless 40.85%
    Sweet 31.93%
    Pungent 25.73%
    Fermented 25.22%
    Solvent 23.72%
    Sharp 20.43%
    Fresh 18.35%

     

    Flavor
    Sulfurous 39.88%
    Odorless 38.51%
    Sulfury 28.7%
    Sweet 27.33%
    Onion 26.62%
    Meaty 25.33%
    Roasted 24.3%
    Soup 22.5%
    Sweet-like 21.87%
    Fishy 21.83%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    5.31 (weak acid)

    Molecular weight
    114.96 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -42.7 °F (EPA, 1998)
    • -41.5 °C
    • -42 °C
    • -43 °F

    Boiling point

    • 223 °F at 760 mmHg (EPA, 1998)
    • 104 °C
    • 104-106 °C
    • 223 °F

    Flash point

    • 40.82 ˚C est.
    • Less than 66.2F (EPA, 1998)
    • Flash point < 19 °C
    • <19 °C (closed cup)
    • <66 °F

    Solubility expt.

    • Reacts with water (NIOSH, 2024)
    • In water, 1,020 mg/L at 25 °C
    • In water, 2.20X10+4 mg/L at 25 °C
    • Miscible with ethanol, ethyl ether
    • Miscible with many organic solvents
    • Solubility in water: reaction

  • Synonyms

    • BIS(CHLOROMETHYL) ETHER
    • 542-88-1
    • Bis(chloromethyl)ether
    • Chloro(chloromethoxy)methane
    • Chloromethyl ether
    • sym-Dichloromethyl ether
    • BCME
    • Methane, oxybis[chloro-
    • Oxybis(chloromethane)
    • Dichloromethyl ether
    • Ether, bis(chloromethyl)
    • Dichlorodimethyl ether
    • Oxybis[chloromethane]
    • Monochloromethyl Ether
    • Bis-CME
    • sym-Dichloro-dimethyl ether
    • Dichloromethyl ether, symmetrical
    • Dichlordimethylaether
    • RCRA waste number P016
    • CCRIS 90
    • 1,1'-Dichlorodimethyl ether
    • Dimethyl-1,1'-dichloroether
    • HSDB 501
    • Bis-(chloromethyl)ether
    • Methane, oxybis(chloro-
    • Dichlorodimethyl ether, symmetrical
    • EINECS 208-832-8
    • UN2249
    • BRN 1679223
    • DTXSID8020173
    • UNII-77382IHE37
    • CHEBI:82270
    • alpha,alpha'-Dichlorodimethyl ether
    • (Monochloromethyl) ether
    • s-Di(chloromethyl) ether
    • DTXCID40173
    • Methane, 1,1'-oxybis(1-chloro-
    • Methane, 1,1'-oxybis[1-chloro-
    • 4-01-00-03051 (Beilstein Handbook Reference)
    • 77382IHE37
    • BIS(CHLOROMETHYL) ETHER [HSDB]
    • UN 2249
    • Ether, Chloromethyl
    • Dichlordimethylaether [German]
    • Ether, Dichloromethyl
    • Methane, oxybis(chloro)-
    • RCRA waste no. P016
    • chloromethylether
    • Bis(chloromethyl)ether (BCME)
    • chloro methylether
    • Bis-chloromethyl-ether
    • symDichloromethyl ether
    • Methane, oxybis(chloro
    • 1,1'-Oxybis
    • symDichlorodimethyl ether
    • Dimethyl1,1'dichloroether
    • SCHEMBL998
    • 1,1'Dichlorodimethyl ether
    • Chloro(chloromethoxy) methane
    • CHEMBL3185875
    • chloro-(chloromethyloxy)-methane
    • Chloro(chloromethoxy)methane fume
    • DICHLORINATED METHYL OXIDE
    • Tox21_200840
    • STL280338
    • SYM-DICHLOROMETHYL ETHER [MI]
    • AKOS006273599
    • Bis(chloromethyl) ether (ACGIH:OSHA)
    • .alpha.,.alpha.'-Dichlorodimethyl ether
    • NCGC00248846-01
    • NCGC00258394-01
    • CAS-542-88-1
    • FC183332
    • DB-007292
    • NS00001879
    • B18900
    • C19158
    • EN300-225762
    • Q2283186
    • Dichlorodimethyl ether, symmetrical [UN2249] [Poison]
    • Chloro(chloromethoxy)methane, 0.5 M dichloromethane solution

  • Applications

    Bis(Chloromethyl) Ether (CAS 542-88-1) is a reactive industrial chemical used mainly as an intermediate for synthesizing chloromethylating agents and for introducing chloromethyl groups into polymers and resins. In the polymer and plastics sector, it is commonly used to chloromethylate phenolic derivatives or similar backbone compounds to generate chloromethylated intermediates for subsequent crosslinking or functionalization. In coatings and inks, it serves as a reactive functionalization and crosslinking reagent for resin systems to improve adhesion and durability. In adhesives, it is used to prepare chloromethyl-functionalized resins that enhance bonding. Handling and use are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 204.65
    methanol 225.74
    isopropanol 164.39
    water 22.69
    ethyl acetate 144.79
    n-propanol 155.13
    acetone 446.17
    n-butanol 132.5
    acetonitrile 254.69
    DMF 712.46
    toluene 65.86
    isobutanol 110.83
    1,4-dioxane 326.35
    methyl acetate 219.95
    THF 478.34
    2-butanone 245.89
    n-pentanol 81.08
    sec-butanol 133.16
    n-hexane 17.46
    ethylene glycol 109.86
    NMP 646.96
    cyclohexane 64.8
    DMSO 763.45
    n-butyl acetate 116.62
    n-octanol 54.16
    chloroform 595.84
    n-propyl acetate 109.1
    acetic acid 614.39
    dichloromethane 508.29
    cyclohexanone 324.27
    propylene glycol 93.32
    isopropyl acetate 88.46
    DMAc 523.99
    2-ethoxyethanol 183.65
    isopentanol 97.75
    n-heptane 35.91
    ethyl formate 136.24
    1,2-dichloroethane 296.28
    n-hexanol 79.09
    2-methoxyethanol 327.21
    isobutyl acetate 63.42
    tetrachloromethane 158.99
    n-pentyl acetate 80.35
    transcutol 366.34
    n-heptanol 55.48
    ethylbenzene 36.03
    MIBK 92.38
    2-propoxyethanol 156.57
    tert-butanol 211.5
    MTBE 130.09
    2-butoxyethanol 120.1
    propionic acid 204.98
    o-xylene 66.94
    formic acid 271.37
    diethyl ether 136.42
    m-xylene 50.13
    p-xylene 59.09
    chlorobenzene 122.99
    dimethyl carbonate 80.12
    n-octane 12.49
    formamide 387.84
    cyclopentanone 435.71
    2-pentanone 174.06
    anisole 105.11
    cyclopentyl methyl ether 212.21
    gamma-butyrolactone 408.46
    1-methoxy-2-propanol 223.15
    pyridine 344.23
    3-pentanone 161.06
    furfural 429.98
    n-dodecane 8.55
    diethylene glycol 149.4
    diisopropyl ether 42.8
    tert-amyl alcohol 150.31
    acetylacetone 214.73
    n-hexadecane 9.64
    acetophenone 131.16
    methyl propionate 147.36
    isopentyl acetate 92.08
    trichloroethylene 639.26
    n-nonanol 48.96
    cyclohexanol 184.72
    benzyl alcohol 106.56
    2-ethylhexanol 63.31
    isooctanol 47.38
    dipropyl ether 109.9
    1,2-dichlorobenzene 125.15
    ethyl lactate 66.32
    propylene carbonate 179.52
    n-methylformamide 317.96
    2-pentanol 93.36
    n-pentane 30.04
    1-propoxy-2-propanol 136.6
    1-methoxy-2-propyl acetate 116.26
    2-(2-methoxypropoxy) propanol 110.45
    mesitylene 37.93
    ε-caprolactone 239.83
    p-cymene 50.73
    epichlorohydrin 389.51
    1,1,1-trichloroethane 339.56
    2-aminoethanol 156.08
    morpholine-4-carbaldehyde 457.67
    sulfolane 527.68
    2,2,4-trimethylpentane 17.26
    2-methyltetrahydrofuran 316.76
    n-hexyl acetate 87.5
    isooctane 10.77
    2-(2-butoxyethoxy)ethanol 132.64
    sec-butyl acetate 65.81
    tert-butyl acetate 104.76
    decalin 17.85
    glycerin 158.84
    diglyme 312.84
    acrylic acid 247.06
    isopropyl myristate 41.08
    n-butyric acid 207.42
    acetyl acetate 110.73
    di(2-ethylhexyl) phthalate 45.31
    ethyl propionate 86.15
    nitromethane 668.43
    1,2-diethoxyethane 134.66
    benzonitrile 137.16
    trioctyl phosphate 35.04
    1-bromopropane 151.56
    gamma-valerolactone 428.56
    n-decanol 36.86
    triethyl phosphate 65.41
    4-methyl-2-pentanol 49.57
    propionitrile 143.98
    vinylene carbonate 171.92
    1,1,2-trichlorotrifluoroethane 448.5
    DMS 76.62
    cumene 31.7
    2-octanol 40.21
    2-hexanone 114.32
    octyl acetate 53.16
    limonene 89.48
    1,2-dimethoxyethane 294.22
    ethyl orthosilicate 65.59
    tributyl phosphate 41.09
    diacetone alcohol 160.28
    N,N-dimethylaniline 100.27
    acrylonitrile 216.39
    aniline 144.32
    1,3-propanediol 172.51
    bromobenzene 106.9
    dibromomethane 346.81
    1,1,2,2-tetrachloroethane 504.16
    2-methyl-cyclohexyl acetate 86.41
    tetrabutyl urea 70.02
    diisobutyl methanol 53.11
    2-phenylethanol 93.68
    styrene 51.01
    dioctyl adipate 72.74
    dimethyl sulfate 176.64
    ethyl butyrate 110.05
    methyl lactate 97.97
    butyl lactate 72.31
    diethyl carbonate 72.74
    propanediol butyl ether 104.91
    triethyl orthoformate 87.76
    p-tert-butyltoluene 52.11
    methyl 4-tert-butylbenzoate 125.92
    morpholine 400.37
    tert-butylamine 133.9
    n-dodecanol 31.05
    dimethoxymethane 253.22
    ethylene carbonate 129.9
    cyrene 149.78
    2-ethoxyethyl acetate 101.95
    2-ethylhexyl acetate 78.81
    1,2,4-trichlorobenzene 180.34
    4-methylpyridine 246.56
    dibutyl ether 66.96
    2,6-dimethyl-4-heptanol 53.11
    DEF 272.39
    dimethyl isosorbide 199.96
    tetrachloroethylene 398.13
    eugenol 120.0
    triacetin 117.79
    span 80 111.64
    1,4-butanediol 73.74
    1,1-dichloroethane 280.0
    2-methyl-1-pentanol 64.97
    methyl formate 229.56
    2-methyl-1-butanol 98.32
    n-decane 14.07
    butyronitrile 131.43
    3,7-dimethyl-1-octanol 56.79
    1-chlorooctane 42.52
    1-chlorotetradecane 19.64
    n-nonane 14.39
    undecane 10.33
    tert-butylcyclohexane 16.64
    cyclooctane 19.53
    cyclopentanol 238.46
    tetrahydropyran 284.7
    tert-amyl methyl ether 115.11
    2,5,8-trioxanonane 212.74
    1-hexene 44.55
    2-isopropoxyethanol 124.28
    2,2,2-trifluoroethanol 261.3
    methyl butyrate 129.62

    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