Ethylbis(2-chloroethyl)amine

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  • Identifiers

    CAS number
    538-07-8

    Molecular formula
    C6H13Cl2N

    SMILES
    CCN(CCCl)CCCl

  • Odor profile

    Fragrance
    Fishy 82.79%
    Cheesy 55.21%
    Ripe 49.99%
    Animal 32.37%
    Odorless 30.72%
    Oily 19.71%
    Meaty 19.58%
    Savory 19.39%
    Sweet 17.99%
    Cooling 17.97%

     

    Flavor
    Sulfurous 28.35%
    Odorless 24.94%
    Meaty 24.22%
    Fishy 23.81%
    Ammoniacal 23.71%
    Sulfury 22.91%
    Bland 20.41%
    Bloody 20.4%
    Skunky 20.37%
    Glue 20.26%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    5.17 (weak acid)

    Molecular weight
    170.08 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • -29 °F (EPA, 1998)
    • -34 °C
    • Crystals, from acetone; MP: 141 °C /Hydrochloride/

    Boiling point

    • 185 °F at 12 mmHg (EPA, 1998)
    • 194 °C with decomposition

    Flash point

    • 70.08 ˚C est.
    • High enough not to interfere with military use of the agent (EPA, 1998)

    Solubility expt.

    • In water, 160 mg/l @ 25 °C
    • Miscible with many organic solvents
    • Solubility in water at 25 °C: very poor

  • Synonyms

    • Bis(2-chloroethyl)ethylamine
    • 538-07-8
    • ETHYLBIS(2-CHLOROETHYL)AMINE
    • Nitrogen mustard (HN-1)
    • Ethyl-S
    • 2-Chloro-N-(2-chloroethyl)-N-ethylethanamine
    • 2,2'-Dichlorotriethylamine
    • Triethylamine, 2,2'-dichloro-
    • HSDB 6392
    • UNII-B75ZZA7WIG
    • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-ethyl-
    • TL 329
    • TL 1149
    • UN 2810
    • BRN 1735676
    • B75ZZA7WIG
    • HN1
    • Ethyl-bis(2-chloroethyl)amine
    • DTXSID0060220
    • 3-04-00-00241 (Beilstein Handbook Reference)
    • NITROGEN MUSTARD (HN-1) [HSDB]
    • HN-1 cpd
    • Ethylbis(beta-chloroethyl)amine
    • EthylS
    • AI3-16200
    • 2,2'Dichlorotriethylamine
    • : NITROGEN MUSTARD
    • Bis(2chloroethyl)ethylamine
    • Ethylbis(2chloroethyl)amine
    • 2,2'-Dichloro-triethylamine
    • SCHEMBL377126
    • n-ethylbis(2-chloroethyl)amine
    • DTXCID1041504
    • N-ethyl-bis(2-chloroethyl)amine
    • ethane, bis(2-chloroethyl)amino-
    • Ethylbis(.beta.-chloroethyl)amine
    • ethyl-bis-(2-chloro-ethyl)-amine
    • 2ChloroN(2chloroethyl)Nethylethanamine
    • AKOS006278185
    • N,N-Bis(2-chloroethyl)-N-ethylamine #
    • NS00094970
    • 2-Chloro-N-(2-chloroethyl)-N-ethyl-ethanamine
    • Q5635296

  • Applications

    Ethylbis(2-chloroethyl)amine (CAS 538-07-8) is primarily used as a chemical intermediate for the synthesis of nitrogen mustard-type alkylating agents in pharmaceutical research, serving as a reactive building block to introduce 2-chloroethyl groups in organic synthesis; it can function as a crosslinking/functionalizing reagent for polymers, coatings, and adhesives, enabling network formation or property modification; it is involved in process development and the production of specialty chemicals and performance materials; and it is encountered in laboratories as a precursor to various amine derivatives used in research and development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 112.83
    methanol 158.8
    isopropanol 70.53
    water 7.32
    ethyl acetate 93.58
    n-propanol 106.83
    acetone 135.83
    n-butanol 94.95
    acetonitrile 117.4
    DMF 156.96
    toluene 79.76
    isobutanol 75.47
    1,4-dioxane 239.32
    methyl acetate 104.81
    THF 299.99
    2-butanone 115.44
    n-pentanol 72.27
    sec-butanol 82.67
    n-hexane 25.71
    ethylene glycol 61.36
    NMP 289.36
    cyclohexane 94.63
    DMSO 265.81
    n-butyl acetate 140.56
    n-octanol 56.99
    chloroform 548.2
    n-propyl acetate 79.99
    acetic acid 274.27
    dichloromethane 481.72
    cyclohexanone 269.99
    propylene glycol 53.09
    isopropyl acetate 48.78
    DMAc 155.13
    2-ethoxyethanol 113.39
    isopentanol 65.5
    n-heptane 55.44
    ethyl formate 97.77
    1,2-dichloroethane 247.66
    n-hexanol 104.28
    2-methoxyethanol 158.02
    isobutyl acetate 57.14
    tetrachloromethane 187.78
    n-pentyl acetate 85.52
    transcutol 309.63
    n-heptanol 59.57
    ethylbenzene 39.41
    MIBK 38.09
    2-propoxyethanol 143.39
    tert-butanol 85.43
    MTBE 67.79
    2-butoxyethanol 101.43
    propionic acid 137.51
    o-xylene 66.12
    formic acid 133.97
    diethyl ether 82.33
    m-xylene 48.37
    p-xylene 64.59
    chlorobenzene 158.44
    dimethyl carbonate 28.36
    n-octane 17.27
    formamide 116.26
    cyclopentanone 265.67
    2-pentanone 70.68
    anisole 74.45
    cyclopentyl methyl ether 135.36
    gamma-butyrolactone 280.23
    1-methoxy-2-propanol 87.21
    pyridine 256.01
    3-pentanone 76.24
    furfural 307.63
    n-dodecane 12.09
    diethylene glycol 130.47
    diisopropyl ether 23.72
    tert-amyl alcohol 77.81
    acetylacetone 81.36
    n-hexadecane 13.7
    acetophenone 88.65
    methyl propionate 69.54
    isopentyl acetate 109.65
    trichloroethylene 462.58
    n-nonanol 52.28
    cyclohexanol 162.55
    benzyl alcohol 84.56
    2-ethylhexanol 89.82
    isooctanol 50.59
    dipropyl ether 114.17
    1,2-dichlorobenzene 150.63
    ethyl lactate 49.29
    propylene carbonate 152.35
    n-methylformamide 107.89
    2-pentanol 53.33
    n-pentane 29.6
    1-propoxy-2-propanol 122.15
    1-methoxy-2-propyl acetate 94.2
    2-(2-methoxypropoxy) propanol 101.3
    mesitylene 34.27
    ε-caprolactone 210.37
    p-cymene 61.15
    epichlorohydrin 253.04
    1,1,1-trichloroethane 263.78
    2-aminoethanol 81.97
    morpholine-4-carbaldehyde 235.2
    sulfolane 355.92
    2,2,4-trimethylpentane 16.99
    2-methyltetrahydrofuran 241.5
    n-hexyl acetate 94.61
    isooctane 7.96
    2-(2-butoxyethoxy)ethanol 122.83
    sec-butyl acetate 48.56
    tert-butyl acetate 52.28
    decalin 27.57
    glycerin 87.5
    diglyme 231.61
    acrylic acid 150.27
    isopropyl myristate 48.14
    n-butyric acid 142.05
    acetyl acetate 76.95
    di(2-ethylhexyl) phthalate 58.11
    ethyl propionate 60.08
    nitromethane 220.54
    1,2-diethoxyethane 129.16
    benzonitrile 126.63
    trioctyl phosphate 42.14
    1-bromopropane 158.44
    gamma-valerolactone 285.5
    n-decanol 41.47
    triethyl phosphate 69.41
    4-methyl-2-pentanol 28.72
    propionitrile 98.96
    vinylene carbonate 164.61
    1,1,2-trichlorotrifluoroethane 271.81
    DMS 70.16
    cumene 35.09
    2-octanol 41.14
    2-hexanone 75.65
    octyl acetate 61.47
    limonene 100.76
    1,2-dimethoxyethane 166.11
    ethyl orthosilicate 69.71
    tributyl phosphate 52.61
    diacetone alcohol 61.88
    N,N-dimethylaniline 64.51
    acrylonitrile 126.98
    aniline 125.26
    1,3-propanediol 91.39
    bromobenzene 157.54
    dibromomethane 335.22
    1,1,2,2-tetrachloroethane 368.6
    2-methyl-cyclohexyl acetate 102.43
    tetrabutyl urea 68.98
    diisobutyl methanol 50.87
    2-phenylethanol 98.92
    styrene 53.52
    dioctyl adipate 81.99
    dimethyl sulfate 63.07
    ethyl butyrate 104.22
    methyl lactate 51.13
    butyl lactate 71.62
    diethyl carbonate 77.36
    propanediol butyl ether 79.26
    triethyl orthoformate 95.89
    p-tert-butyltoluene 57.82
    methyl 4-tert-butylbenzoate 92.93
    morpholine 252.5
    tert-butylamine 66.65
    n-dodecanol 35.53
    dimethoxymethane 78.9
    ethylene carbonate 132.23
    cyrene 112.65
    2-ethoxyethyl acetate 100.85
    2-ethylhexyl acetate 107.37
    1,2,4-trichlorobenzene 187.5
    4-methylpyridine 176.93
    dibutyl ether 80.87
    2,6-dimethyl-4-heptanol 50.87
    DEF 102.44
    dimethyl isosorbide 175.93
    tetrachloroethylene 337.92
    eugenol 97.62
    triacetin 101.99
    span 80 109.39
    1,4-butanediol 52.11
    1,1-dichloroethane 206.39
    2-methyl-1-pentanol 59.93
    methyl formate 92.44
    2-methyl-1-butanol 75.07
    n-decane 20.06
    butyronitrile 94.56
    3,7-dimethyl-1-octanol 57.38
    1-chlorooctane 54.68
    1-chlorotetradecane 26.6
    n-nonane 20.58
    undecane 14.9
    tert-butylcyclohexane 22.4
    cyclooctane 27.05
    cyclopentanol 160.79
    tetrahydropyran 256.18
    tert-amyl methyl ether 64.49
    2,5,8-trioxanonane 175.03
    1-hexene 54.54
    2-isopropoxyethanol 79.26
    2,2,2-trifluoroethanol 128.56
    methyl butyrate 81.9

    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