Mechlorethamine

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  • Identifiers

    CAS number
    51-75-2

    Molecular formula
    C5H11Cl2N

    SMILES
    CN(CCCl)CCCl

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Fishy 81.98%
    Cheesy 55.78%
    Ripe 50.78%
    Odorless 30.62%
    Animal 29.05%
    Oily 20.63%
    Meaty 19.43%
    Savory 18.78%
    Sweet 16.81%
    Cooling 16.53%

     

    Flavor
    Sulfurous 30.22%
    Odorless 24.45%
    Meaty 24.44%
    Fishy 24.04%
    Sulfury 23.86%
    Ammoniacal 22.34%
    Bloody 20.3%
    Glue 20.27%
    Skunky 20.13%
    Bland 19.92%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    5.02 (weak acid)

    Molecular weight
    156.05 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Melting point expt.

    • -76 °F (EPA, 1998)
    • 108 - 110°C
    • -60 °C
    • 109-110 °C
    • 108 - 111 °C

    Boiling point

    • 189 °F at 18 mmHg (EPA, 1998)
    • 87°C at 1.80E+01 mm Hg
    • 87 °C @ 18 mm Hg

    Flash point

    • 65.61 ˚C est.

    Solubility expt.

    • Very soluble
    • Very slightly soluble in water; miscible with dimethyl formamide, carbon disulfide, carbon tetrachloride, many organic solvents and oils
    • Sol in water
    • FREELY SOL IN ETHANOL; SLIGHTLY SOL IN BENZENE, ETHER
    • 3.34e+01 g/L

  • Synonyms

    • mechlorethamine
    • Chlormethine
    • Nitrogen mustard
    • Chlorethazine
    • Mustine
    • Mustargen
    • 51-75-2
    • Cloramin
    • Embichin
    • Mecloretamina
    • Caryolysine
    • Bis(2-chloroethyl)methylamine
    • 2-Chloro-N-(2-chloroethyl)-N-methylethanamine
    • Mechloroethamine
    • 2,2'-Dichloro-N-methyldiethylamine
    • Methylbis(2-chloroethyl)amine
    • Antimit
    • Dichlor amine
    • N-Methyl-bis(2-chloroethyl)amine
    • N-Methyl lost
    • N-Methyl-lost
    • Bis(beta-chloroethyl)methylamine
    • Methylbis(beta-chloroethyl)amine
    • Clormetina
    • Mustine note
    • N-Methyl-bis(beta-chloroethyl)amine
    • Di(2-chloroethyl)methylamine
    • Methyldi(2-chloroethyl)amine
    • Mecloretamina [Italian]
    • N,N-Bis(2-chloroethyl)methylamine
    • beta,beta'-Dichlorodiethyl-N-methylamine
    • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-
    • N-Methyl-lost [German]
    • Nitrogranulogen
    • N,N-Di(chloroethyl)methylamine
    • Clormetina [INN-Spanish]
    • Nitrogen mustard (HN-2)
    • Chlormethinum [INN-Latin]
    • 2,2'-Dichlorodiethyl-methylamine
    • NSC 762
    • N-Methyl-bis-chloraethylamin
    • N-Methyl-2,2'-dichlorodiethylamine
    • ENT-25294
    • N-Lost
    • NSC-10107
    • HN-2
    • Valchlor
    • Diethylamine, 2,2'-dichloro-N-methyl-
    • Chlormethine (INN)
    • CCRIS 447
    • TL 146
    • N-Methyl-bis-chloraethylamin [German]
    • Ledaga
    • HN2
    • T-1024
    • CHEBI:28925
    • HSDB 5083
    • Nitrogen mustard (hn 2)
    • UNII-50D9XSG0VR
    • EINECS 200-120-5
    • 50D9XSG0VR
    • T 1024
    • Eraso (Salt/Mix)
    • Nitol (Salt/Mix)
    • NSC-757087
    • UN 2927
    • BRN 0605323
    • Hn2 (amine)
    • bis(2-chloroethyl)(methyl)amine
    • Embichin (Salt/Mix)
    • Dichloren (Salt/Mix)
    • Caryolysin (Salt/Mix)
    • Caryolysine (Salt/Mix)
    • NSC 10107
    • CHLORMETHINE [INN]
    • NSC-128663
    • MECHLORETHAMINE [MI]
    • Bis(b-chloroethyl)methylamine
    • CHLORMETHINE [WHO-DD]
    • MECHLORETHAMINE [HSDB]
    • MECHLORETHAMINE [VANDF]
    • Methyl-bis(2-chloroethyl)amine
    • NITROGEN MUSTARD [IARC]
    • N-methylbis(2-chloroethyl)amine
    • DTXSID2020975
    • .Beta.,.beta.'-Dichlorodiethyl-N-methylamine
    • Bis(.beta.-chloroethyl)methylamine
    • Methylbis(.beta.-chloroethyl)amine
    • N-Methyl-bis(.beta.-chloroethyl)amine
    • Caryolysin
    • Stickstofflost (ebewe)
    • Clormetina (INN-Spanish)
    • Chlormethinum (INN-Latin)
    • Methylchlorethamine
    • AB00052033_05
    • METHYL-.BETA.,.BETA.-DICHLORODIETHYLAMINE
    • N-LOST (GERMAN)
    • NITROGEN MUSTARD (IARC)
    • DICHLOREN (GERMAN)
    • Chloramine (the nitrogen mustard)
    • Chlormethine [INN:BAN]
    • N-METHYL-BIS-CHLORAETHYLAMIN (GERMAN)
    • Mechlorethamine N-Oxide
    • Nitol (*Hydrochloride*)
    • Mitoxine (*Hydrochloride*)
    • chloromethine
    • NMethylLost
    • SR-05000001664
    • nitrogen mustards
    • Stickstofflost (*Hydrochloride*)
    • Mechlorethamine Hydrochloride N-Oxide
    • N,N-Bis(2-chloroethyl)-N-methylamine
    • NMethylLost (German)
    • Chlormethinehydrochloride
    • Spectrum_000889
    • N-METHYL-DI(2-CHLORO)-ETHYLAMINE
    • NMethylbischloraethylamin
    • Spectrum2_000448
    • Spectrum3_000484
    • Spectrum4_000924
    • Spectrum5_001702
    • bis(chloroethyl)methylamine
    • CHEMBL427
    • Epitope ID:116224
    • Di(2chloroethyl)methylamine
    • Methyldi(2chloroethyl)amine
    • cid_4033
    • SCHEMBL3861

  • Applications

    Mechlorethamine is a potent alkylating agent primarily used in the pharmaceutical field as a chemotherapy drug (a nitrogen mustard) for certain cancers, including topical formulations for cutaneous T-cell lymphoma; in drug development and manufacturing it can serve as an intermediate for the synthesis of other nitrogen mustard anticancer agents; it is also handled as a research reagent in organic synthesis and pharmacology under strict safety controls due to its vesicant properties; its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 142.16
    methanol 213.04
    isopropanol 80.04
    water 38.12
    ethyl acetate 66.62
    n-propanol 115.66
    acetone 111.8
    n-butanol 92.58
    acetonitrile 97.64
    DMF 153.73
    toluene 41.41
    isobutanol 75.52
    1,4-dioxane 171.33
    methyl acetate 93.49
    THF 223.07
    2-butanone 91.32
    n-pentanol 59.26
    sec-butanol 82.32
    n-hexane 14.21
    ethylene glycol 102.8
    NMP 263.09
    cyclohexane 53.01
    DMSO 191.79
    n-butyl acetate 98.04
    n-octanol 49.48
    chloroform 404.21
    n-propyl acetate 56.09
    acetic acid 393.8
    dichloromethane 325.21
    cyclohexanone 195.63
    propylene glycol 77.28
    isopropyl acetate 32.45
    DMAc 145.59
    2-ethoxyethanol 112.15
    isopentanol 56.31
    n-heptane 39.52
    ethyl formate 81.59
    1,2-dichloroethane 153.42
    n-hexanol 90.25
    2-methoxyethanol 179.69
    isobutyl acetate 39.54
    tetrachloromethane 138.38
    n-pentyl acetate 63.07
    transcutol 266.07
    n-heptanol 57.38
    ethylbenzene 20.45
    MIBK 24.77
    2-propoxyethanol 135.59
    tert-butanol 83.84
    MTBE 47.9
    2-butoxyethanol 101.31
    propionic acid 157.09
    o-xylene 40.11
    formic acid 247.63
    diethyl ether 57.07
    m-xylene 27.53
    p-xylene 35.27
    chlorobenzene 88.85
    dimethyl carbonate 25.2
    n-octane 11.37
    formamide 185.57
    cyclopentanone 202.71
    2-pentanone 49.88
    anisole 48.57
    cyclopentyl methyl ether 97.5
    gamma-butyrolactone 225.36
    1-methoxy-2-propanol 91.76
    pyridine 176.34
    3-pentanone 56.81
    furfural 260.17
    n-dodecane 8.13
    diethylene glycol 139.62
    diisopropyl ether 15.66
    tert-amyl alcohol 76.78
    acetylacetone 55.95
    n-hexadecane 8.94
    acetophenone 62.87
    methyl propionate 60.39
    isopentyl acetate 75.02
    trichloroethylene 307.79
    n-nonanol 44.95
    cyclohexanol 136.3
    benzyl alcohol 63.46
    2-ethylhexanol 72.72
    isooctanol 45.25
    dipropyl ether 81.98
    1,2-dichlorobenzene 91.23
    ethyl lactate 43.32
    propylene carbonate 120.28
    n-methylformamide 129.77
    2-pentanol 47.92
    n-pentane 19.84
    1-propoxy-2-propanol 114.32
    1-methoxy-2-propyl acetate 71.65
    2-(2-methoxypropoxy) propanol 93.06
    mesitylene 18.93
    ε-caprolactone 159.11
    p-cymene 42.04
    epichlorohydrin 182.87
    1,1,1-trichloroethane 165.82
    2-aminoethanol 126.87
    morpholine-4-carbaldehyde 198.57
    sulfolane 269.34
    2,2,4-trimethylpentane 11.53
    2-methyltetrahydrofuran 173.6
    n-hexyl acetate 70.63
    isooctane 5.29
    2-(2-butoxyethoxy)ethanol 112.21
    sec-butyl acetate 32.6
    tert-butyl acetate 35.7
    decalin 15.09
    glycerin 124.6
    diglyme 191.6
    acrylic acid 183.9
    isopropyl myristate 33.54
    n-butyric acid 139.7
    acetyl acetate 54.2
    di(2-ethylhexyl) phthalate 47.26
    ethyl propionate 43.14
    nitromethane 245.77
    1,2-diethoxyethane 85.85
    benzonitrile 83.72
    trioctyl phosphate 34.91
    1-bromopropane 95.25
    gamma-valerolactone 222.7
    n-decanol 35.55
    triethyl phosphate 51.33
    4-methyl-2-pentanol 23.67
    propionitrile 80.21
    vinylene carbonate 128.41
    1,1,2-trichlorotrifluoroethane 248.04
    DMS 52.45
    cumene 20.25
    2-octanol 35.27
    2-hexanone 51.49
    octyl acetate 46.48
    limonene 69.18
    1,2-dimethoxyethane 124.01
    ethyl orthosilicate 53.49
    tributyl phosphate 40.8
    diacetone alcohol 52.86
    N,N-dimethylaniline 45.16
    acrylonitrile 112.55
    aniline 94.19
    1,3-propanediol 116.24
    bromobenzene 77.62
    dibromomethane 233.3
    1,1,2,2-tetrachloroethane 252.0
    2-methyl-cyclohexyl acetate 75.83
    tetrabutyl urea 55.19
    diisobutyl methanol 37.95
    2-phenylethanol 77.04
    styrene 27.18
    dioctyl adipate 59.22
    dimethyl sulfate 53.37
    ethyl butyrate 75.02
    methyl lactate 50.93
    butyl lactate 61.1
    diethyl carbonate 55.56
    propanediol butyl ether 80.97
    triethyl orthoformate 72.18
    p-tert-butyltoluene 40.43
    methyl 4-tert-butylbenzoate 78.69
    morpholine 198.75
    tert-butylamine 61.09
    n-dodecanol 29.47
    dimethoxymethane 65.93
    ethylene carbonate 99.59
    cyrene 98.72
    2-ethoxyethyl acetate 75.59
    2-ethylhexyl acetate 72.93
    1,2,4-trichlorobenzene 126.24
    4-methylpyridine 118.68
    dibutyl ether 50.53
    2,6-dimethyl-4-heptanol 37.95
    DEF 81.04
    dimethyl isosorbide 144.92
    tetrachloroethylene 247.36
    eugenol 85.46
    triacetin 84.49
    span 80 102.32
    1,4-butanediol 57.74
    1,1-dichloroethane 132.54
    2-methyl-1-pentanol 47.28
    methyl formate 102.24
    2-methyl-1-butanol 69.24
    n-decane 12.91
    butyronitrile 69.83
    3,7-dimethyl-1-octanol 45.66
    1-chlorooctane 36.9
    1-chlorotetradecane 17.91
    n-nonane 13.15
    undecane 9.79
    tert-butylcyclohexane 13.59
    cyclooctane 14.88
    cyclopentanol 152.38
    tetrahydropyran 171.42
    tert-amyl methyl ether 46.63
    2,5,8-trioxanonane 148.24
    1-hexene 32.0
    2-isopropoxyethanol 74.13
    2,2,2-trifluoroethanol 190.12
    methyl butyrate 60.19

    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