Bis(2-chloroethoxy)methane

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  • Identifiers

    CAS number
    111-91-1

    Molecular formula
    C5H10Cl2O2

    SMILES
    C(CCl)OCOCCCl

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Alcoholic 43.4%
    Odorless 37.21%
    Ethereal 35.78%
    Fruity 32.89%
    Sweet 29.76%
    Fishy 23.41%
    Solvent 22.7%
    Oily 21.85%
    Fresh 20.74%
    Fermented 20.13%

     

    Flavor
    Sulfurous 44.26%
    Odorless 31.4%
    Onion 30.76%
    Sulfury 29.07%
    Sweet 28.48%
    Meaty 28.33%
    Roasted 28.27%
    Vegetable 24.67%
    Fishy 23.91%
    Fatty 23.67%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    5.31 (weak acid)

    Molecular weight
    173.03 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • Freezing point= -32.8 °C

    Boiling point

    • 424.6 °F at 760 mmHg (NTP, 1992)
    • 218.1 °C

    Flash point

    • 93.58 ˚C est.
    • 230 °F (NTP, 1992)
    • 230 °F (110 °C) (OPEN CUP)

    Solubility expt.

    • ... Miscible with most organic solvents.
    • In water, 7,800 mg/l at 20 °C

  • Synonyms

    • BIS(2-CHLOROETHOXY)METHANE
    • 111-91-1
    • Dichloroethylformal
    • Dichloroethyl formal
    • 2,2-Dichloroethylformal
    • Bis(2-chloroethyl) formal
    • Di-2-chloroethyl formal
    • Methane, bis(2-chloroethoxy)-
    • Di(2-chloroethyl)formal
    • Bis(2-chloroethyl)formal
    • Dichlorodiethyl formal
    • Dichlorodiethyl methylal
    • Formaldehyde bis(2-chloroethyl) acetal
    • Bis(2-chloroethoxy)-methane
    • 2,2-Dichloroethyl formal
    • Bis(beta-chloroethyl)formal
    • Bis(beta-chloroethyl) formal
    • DTXSID4023917
    • Ethane, 1,1'-(methylenebis(oxy))bis(2-chloro-
    • Formaldehyde bis(beta-chloroethyl) acetal
    • NSC-5212
    • DTXCID203917
    • 5288KK0810
    • DI(2-CHLOROETHOXY)METHANE
    • Ethane, 1,1'-[methylenebis(oxy)]bis[2-chloro-
    • 1,7-DICHLORO-3,5-DIOXAHEPTANE
    • RefChem:120073
    • Ethane, 2,2'-(methylenebis(oxy))bis(1-chloro)-
    • BIS(BETACHLOROETHYL) FORMAL
    • 203-920-2
    • Dichloromethoxy ethane
    • 1-chloro-2-(2-chloroethoxymethoxy)ethane
    • RCRA waste number U024
    • NSC 5212
    • Bis(.beta.-chloroethyl) formal
    • 1-Chloro-2-[(2-chloroethoxy)methoxy]ethane
    • Formaldehyde bis(.beta.-chloroethyl) acetal
    • MFCD00045293
    • Bis-(2-chloroethoxy)methane 100 microg/mL in Cyclohexane
    • 2-chloro-1-[(2-chloroethoxy)methoxy]ethane
    • Ethane,1'-[methylenebis(oxy)]bis(2-chloro-
    • Ethane,1'-[methylenebis(oxy)]bis[2-chloro-
    • HSDB 1333
    • EINECS 203-920-2
    • RCRA waste no. U024
    • BRN 1698909
    • bis-(2-Chloroethoxy)methane
    • AI3-01455
    • UNII-5288KK0810
    • EC 203-920-2
    • WLN: G2O1O2G
    • 4-01-00-03028 (Beilstein Handbook Reference)
    • MLS001065594
    • SCHEMBL113160
    • SCHEMBL113161
    • CHEMBL1893366
    • NSC5212
    • HMS3039L16
    • Tox21_200284
    • SBB060138
    • BIS(.BETA.-CHLOROETHYL)FORMAL
    • AKOS006275640
    • MSK001248-100M
    • 2,2-DICHLOROETHYL FORMAL [HSDB]
    • NCGC00091442-01
    • NCGC00091442-02
    • NCGC00257838-01
    • CAS-111-91-1
    • SMR000568470
    • DB-022653
    • NS00005014
    • ST51046373
    • 1-Chloro-2-[(2-chloroethoxy)methoxy]ethane #
    • H20645
    • Q27260978
    • 1-Chloro-2-[(2-chloroethoxy)methoxy]ethane, AldrichCPR
    • Bis(2-chloroethoxy)methane Solution in Methanol, 100ug/mL
    • 111-91-1

  • Applications

    Bis(2-chloroethoxy)methane (CAS 111-91-1) is a bifunctional chloromethyl ether–type compound primarily used as a synthetic intermediate and as a crosslinking/alkylating reagent for polymers. In industrial manufacturing, it can serve as a crosslinking agent for epoxy and phenolic resins, aiding the formation of polymer networks in coatings, paints, and adhesives. It also acts as a feedstock for making chloromethyl derivatives and other specialty chemicals. Additionally, it may be used as a precursor in electronics encapsulation materials and packaging polymers requiring strong interfacial bonding. Its use is subject to local regulations and handling controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 621.69
    methanol 809.42
    isopropanol 489.46
    water 62.79
    ethyl acetate 502.57
    n-propanol 466.53
    acetone 1368.55
    n-butanol 385.35
    acetonitrile 1339.02
    DMF 1349.26
    toluene 276.08
    isobutanol 339.5
    1,4-dioxane 982.74
    methyl acetate 633.1
    THF 1289.83
    2-butanone 708.86
    n-pentanol 278.08
    sec-butanol 393.52
    n-hexane 108.83
    ethylene glycol 215.3
    NMP 1203.42
    cyclohexane 383.2
    DMSO 1886.96
    n-butyl acetate 434.15
    n-octanol 166.58
    chloroform 2886.87
    n-propyl acetate 455.5
    acetic acid 2151.77
    dichloromethane 2784.76
    cyclohexanone 1101.82
    propylene glycol 176.25
    isopropyl acetate 270.39
    DMAc 1056.87
    2-ethoxyethanol 545.36
    isopentanol 273.29
    n-heptane 166.71
    ethyl formate 469.95
    1,2-dichloroethane 1329.44
    n-hexanol 234.14
    2-methoxyethanol 741.5
    isobutyl acetate 251.17
    tetrachloromethane 563.49
    n-pentyl acetate 272.41
    transcutol 1005.94
    n-heptanol 141.58
    ethylbenzene 155.43
    MIBK 213.62
    2-propoxyethanol 394.09
    tert-butanol 531.86
    MTBE 364.49
    2-butoxyethanol 274.23
    propionic acid 635.22
    o-xylene 217.14
    formic acid 835.8
    diethyl ether 508.17
    m-xylene 160.04
    p-xylene 282.41
    chlorobenzene 504.92
    dimethyl carbonate 191.06
    n-octane 56.0
    formamide 1004.02
    cyclopentanone 1133.57
    2-pentanone 445.89
    anisole 338.59
    cyclopentyl methyl ether 599.29
    gamma-butyrolactone 1117.78
    1-methoxy-2-propanol 443.12
    pyridine 1166.11
    3-pentanone 425.87
    furfural 1186.17
    n-dodecane 32.61
    diethylene glycol 335.83
    diisopropyl ether 125.7
    tert-amyl alcohol 384.5
    acetylacetone 491.22
    n-hexadecane 36.31
    acetophenone 400.08
    methyl propionate 397.82
    isopentyl acetate 306.75
    trichloroethylene 2518.28
    n-nonanol 141.68
    cyclohexanol 602.94
    benzyl alcohol 322.63
    2-ethylhexanol 196.79
    isooctanol 120.56
    dipropyl ether 414.78
    1,2-dichlorobenzene 466.69
    ethyl lactate 195.67
    propylene carbonate 555.06
    n-methylformamide 791.44
    2-pentanol 262.97
    n-pentane 126.33
    1-propoxy-2-propanol 339.57
    1-methoxy-2-propyl acetate 268.38
    2-(2-methoxypropoxy) propanol 253.88
    mesitylene 111.3
    ε-caprolactone 733.04
    p-cymene 152.1
    epichlorohydrin 1001.95
    1,1,1-trichloroethane 1220.66
    2-aminoethanol 315.54
    morpholine-4-carbaldehyde 1013.76
    sulfolane 1195.71
    2,2,4-trimethylpentane 53.03
    2-methyltetrahydrofuran 915.57
    n-hexyl acetate 297.53
    isooctane 26.61
    2-(2-butoxyethoxy)ethanol 320.23
    sec-butyl acetate 241.61
    tert-butyl acetate 244.8
    decalin 83.49
    glycerin 285.88
    diglyme 765.17
    acrylic acid 720.24
    isopropyl myristate 124.79
    n-butyric acid 662.23
    acetyl acetate 421.17
    di(2-ethylhexyl) phthalate 123.86
    ethyl propionate 331.11
    nitromethane 2174.53
    1,2-diethoxyethane 470.68
    benzonitrile 548.77
    trioctyl phosphate 97.14
    1-bromopropane 755.04
    gamma-valerolactone 1099.54
    n-decanol 103.62
    triethyl phosphate 219.73
    4-methyl-2-pentanol 116.65
    propionitrile 617.95
    vinylene carbonate 603.35
    1,1,2-trichlorotrifluoroethane 1042.18
    DMS 246.44
    cumene 113.23
    2-octanol 121.99
    2-hexanone 409.1
    octyl acetate 161.91
    limonene 262.48
    1,2-dimethoxyethane 974.41
    ethyl orthosilicate 215.56
    tributyl phosphate 130.54
    diacetone alcohol 281.96
    N,N-dimethylaniline 277.42
    acrylonitrile 863.91
    aniline 451.82
    1,3-propanediol 386.82
    bromobenzene 494.9
    dibromomethane 1863.35
    1,1,2,2-tetrachloroethane 1803.8
    2-methyl-cyclohexyl acetate 275.25
    tetrabutyl urea 195.64
    diisobutyl methanol 132.47
    2-phenylethanol 236.37
    styrene 244.28
    dioctyl adipate 228.11
    dimethyl sulfate 364.4
    ethyl butyrate 415.07
    methyl lactate 200.56
    butyl lactate 208.25
    diethyl carbonate 302.51
    propanediol butyl ether 229.62
    triethyl orthoformate 332.64
    p-tert-butyltoluene 134.1
    methyl 4-tert-butylbenzoate 269.56
    morpholine 1125.79
    tert-butylamine 374.02
    n-dodecanol 84.14
    dimethoxymethane 542.98
    ethylene carbonate 499.96
    cyrene 312.32
    2-ethoxyethyl acetate 298.61
    2-ethylhexyl acetate 268.95
    1,2,4-trichlorobenzene 566.63
    4-methylpyridine 858.99
    dibutyl ether 300.69
    2,6-dimethyl-4-heptanol 132.47
    DEF 651.34
    dimethyl isosorbide 437.12
    tetrachloroethylene 1469.18
    eugenol 281.16
    triacetin 361.02
    span 80 272.09
    1,4-butanediol 198.96
    1,1-dichloroethane 1245.02
    2-methyl-1-pentanol 213.02
    methyl formate 600.6
    2-methyl-1-butanol 283.71
    n-decane 59.65
    butyronitrile 578.06
    3,7-dimethyl-1-octanol 152.07
    1-chlorooctane 162.43
    1-chlorotetradecane 66.08
    n-nonane 65.43
    undecane 40.88
    tert-butylcyclohexane 62.55
    cyclooctane 94.28
    cyclopentanol 635.27
    tetrahydropyran 1069.22
    tert-amyl methyl ether 286.41
    2,5,8-trioxanonane 508.94
    1-hexene 251.17
    2-isopropoxyethanol 350.28
    2,2,2-trifluoroethanol 790.36
    methyl butyrate 499.51

    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
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Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
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Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
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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