Thiotepa

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  • Identifiers

    CAS number
    52-24-4

    Molecular formula
    C6H12N3PS

    SMILES
    C1CN1P(=S)(N2CC2)N3CC3

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 59.98%
    Fishy 36.9%
    Nutty 18.03%
    Popcorn 16.22%
    Pungent 16.17%
    Cooling 15.61%
    Savory 14.68%
    Roasted 14.35%
    Animal 14.02%
    Cooked 13.77%

     

    Flavor
    Bitter 81.63%
    Odorless 19.88%
    Bland 19.75%
    Sweet-like 16.54%
    Alkaline 15.91%
    Cereal 15.8%
    Rotten 15.55%
    Nitrile 15.41%
    Very strong 15.29%
    Cedarleaf 15.21%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    3.59 (weak acid)

    Molecular weight
    189.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 124.7 °F (NTP, 1992)
    • 51.5 °C

    Boiling point

    • Decomposes at 282 °F (NTP, 1992)
    • 272 °F (decomposes)

    Flash point

    • 152.79 ˚C est.

    Solubility expt.

    • >28.4 [ug/mL] (The mean of the results at pH 7.4)
    • 19 g/100 mL at 77 °F (NTP, 1992)
    • 190000 mg/L (at 25 °C)
    • In water, 19 g/100 mL at 25 °C
    • Freely soluble in alcohol, ether, chloroform; soluble in benzene

  • Synonyms

    • thiotepa
    • 52-24-4
    • THIO-TEPA
    • Triethylenethiophosphoramide
    • Thioplex
    • Thiophosphamide
    • Tespamin
    • Thiofozil
    • Tiofosfamid
    • Girostan
    • Tiofosyl
    • Tri(aziridin-1-yl)phosphine sulfide
    • Oncotepa
    • Tespamine
    • Tiofozil
    • Stepa
    • TESPA
    • Oncotiotepa
    • Thiotef
    • Tifosyl
    • Oncothio-tepa
    • Tio-tef
    • Thio-Tep
    • tepadina
    • Thio-tepa S
    • Tris(1-aziridinyl)phosphine sulfide
    • TIO TEF
    • Ledertepa
    • 1,1',1''-phosphorothioyltriaziridine
    • Tiotepa
    • Thiophosphamidum
    • NSC-6396
    • Thiotriethylenephosphoramide
    • Triethylene thiophosphoramide
    • Tepylute
    • Thiotepum
    • N,N',N''-Triethylenethiophosphoramide
    • Triaziridinylphosphine sulfide
    • Triethylenethiophosphorotriamide
    • Tris(ethylenimino)thiophosphate
    • Thiotepum [INN-Latin]
    • Tiotepa [INN-Spanish]
    • CBC 806495
    • Phosphorothioic acid triethylenetriamide
    • Tris(aziridinyl)phosphine sulfide
    • Phosphine sulfide, tris(1-aziridinyl)-
    • Tri(ethyleneimino)thiophosphoramide
    • Aziridine, 1,1',1''-phosphinothioylidynetris-
    • NCI-C01649
    • NSC 6396
    • CCRIS 586
    • SK 6882
    • HSDB 3258
    • NSC6396
    • Tri-1-aziridinylphosphine sulfide
    • AI3-24916
    • EINECS 200-135-7
    • Tris(1-aziridinyl)phosphine sulphide
    • N,N',N''-Triethylenethiophosphamide
    • Tepadina (TN)
    • Thioplex (TN)
    • Rethio (TN)
    • BRN 0145978
    • 905Z5W3GKH
    • MLS001333083
    • N,N',N''-Triethylenethiophosphortriamide
    • DTXSID0021339
    • WR-45312
    • Thiotepa [USP:INN:BAN:JAN]
    • 1,1',1''-Phosphinothioylidynetrisaziridine
    • Tri(1-aziridinyl)phosphine sulfide
    • N,N',N''-Triethylenephosphorothioic triamide
    • THIOTEPA [HSDB]
    • THIOTEPA [IARC]
    • THIOTEPA [INN]
    • THIOTEPA [JAN]
    • THIOTEPA [MI]
    • THIOTEPA [VANDF]
    • N,N',N''-Tri-1,2-ethanediylthiophosphoramide
    • MFCD00145452
    • THIOTEPA [MART.]
    • THIOTEPA [USP-RS]
    • THIOTEPA [WHO-DD]
    • Thiophosphoramide, N,N',N''-tri-1,2-ethanediyl-
    • Thiotepa (JAN/USP/INN)
    • THIOTEPA [EMA EPAR]
    • AZIRIDINE,1,1',1''-PHOSPHINOTHIOYLIDYNETRIS-
    • N,N',N''-Tri-1,2-ethanediylphosphorothioic triamide
    • MLS003389372
    • THIOTEPA [ORANGE BOOK]
    • CHEBI:9570
    • DTXCID201339
    • Phosphorothioic triamide, N,N',N''-tri-1,2-ethanediyl-
    • AI 3-24916
    • THIOTEPA [USP MONOGRAPH]
    • Phosphorothioic triamide, N,N',N''-triethylene-
    • 4-20-00-00052 (Beilstein Handbook Reference)
    • NCGC00095042-04
    • NCGC00095042-06
    • PHOSPHOROTHIOIC TRI(ETHYLENEAMIDE)
    • THIOTEPA (IARC)
    • Thiotepum (INN-Latin)
    • Tiotepa (INN-Spanish)
    • tris(aziridin-1-yl)-lambda5-phosphanethione
    • tris(aziridin-1-yl)-sulfanylidenephosphorane
    • tris(aziridin-1-yl)-$l^{5}-phosphanethione
    • THIOTEPA (MART.)
    • THIOTEPA (USP-RS)
    • 1,1',1''-PHOSPHINOTHIOYLIDYNETRIS(AZIRIDINE)
    • THIOTEPA (USP MONOGRAPH)
    • Thiotepa (USP:INN:BAN:JAN)
    • Thio Tepa
    • CAS-52-24-4
    • SMR000058542
    • tris(aziridin-1-yl)-$l^(5)-phosphanethione
    • SR-05000001855
    • UNII-905Z5W3GKH
    • Oncothiotepa
    • Thiofosfamide
    • Rethio
    • thiotepa?
    • Thiotepa S
    • Thiotepa (Thioplex)
    • Spectrum_001689
    • WR 45312
    • Thio-TEPA (Standard)
    • Thiophosphoramide, N,N',N''-triethylene-
    • Spectrum2_001557

  • Applications

    Thiotepa (CAS 52-24-4) is an organophosphoramide used across several industrial applications. In agriculture, it is employed as a soil fumigant and nematicide to control pests and pathogens before planting, and it may be used as a seed-treatment for certain systems. In pharmaceuticals, it serves as an alkylating agent in chemotherapy regimens for various cancers, including intravesical therapy for bladder cancer and systemic combination protocols. In chemical manufacturing, it is used as an intermediate or precursor for the synthesis of other organophosphorus compounds and specialty chemicals, functioning as a reagent in organic synthesis under controlled conditions. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.71
    methanol 41.8
    isopropanol 12.09
    water 12.26
    ethyl acetate 20.43
    n-propanol 15.1
    acetone 21.72
    n-butanol 14.21
    acetonitrile 23.2
    DMF 52.07
    toluene 7.9
    isobutanol 9.92
    1,4-dioxane 27.06
    methyl acetate 22.61
    THF 48.54
    2-butanone 18.56
    n-pentanol 9.87
    sec-butanol 9.95
    n-hexane 0.6
    ethylene glycol 21.7
    NMP 82.54
    cyclohexane 1.89
    DMSO 49.57
    n-butyl acetate 19.48
    n-octanol 7.31
    chloroform 62.54
    n-propyl acetate 14.61
    acetic acid 73.82
    dichloromethane 54.07
    cyclohexanone 33.02
    propylene glycol 14.93
    isopropyl acetate 15.28
    DMAc 45.85
    2-ethoxyethanol 32.05
    isopentanol 11.16
    n-heptane 1.65
    ethyl formate 33.44
    1,2-dichloroethane 25.58
    n-hexanol 12.25
    2-methoxyethanol 54.4
    isobutyl acetate 9.74
    tetrachloromethane 14.75
    n-pentyl acetate 17.32
    transcutol 39.2
    n-heptanol 11.21
    ethylbenzene 3.79
    MIBK 12.84
    2-propoxyethanol 36.15
    tert-butanol 11.53
    MTBE 8.75
    2-butoxyethanol 29.98
    propionic acid 29.27
    o-xylene 7.16
    formic acid 104.46
    diethyl ether 11.01
    m-xylene 6.8
    p-xylene 4.92
    chlorobenzene 18.04
    dimethyl carbonate 17.87
    n-octane 0.83
    formamide 100.93
    cyclopentanone 47.13
    2-pentanone 17.8
    anisole 12.43
    cyclopentyl methyl ether 18.66
    gamma-butyrolactone 69.33
    1-methoxy-2-propanol 31.15
    pyridine 34.15
    3-pentanone 13.34
    furfural 94.31
    n-dodecane 0.76
    diethylene glycol 42.27
    diisopropyl ether 4.54
    tert-amyl alcohol 10.93
    acetylacetone 24.17
    n-hexadecane 0.85
    acetophenone 18.4
    methyl propionate 19.46
    isopentyl acetate 17.44
    trichloroethylene 56.86
    n-nonanol 7.56
    cyclohexanol 13.84
    benzyl alcohol 18.73
    2-ethylhexanol 9.03
    isooctanol 9.23
    dipropyl ether 8.74
    1,2-dichlorobenzene 22.42
    ethyl lactate 17.4
    propylene carbonate 47.37
    n-methylformamide 52.04
    2-pentanol 8.68
    n-pentane 1.26
    1-propoxy-2-propanol 25.0
    1-methoxy-2-propyl acetate 26.3
    2-(2-methoxypropoxy) propanol 20.2
    mesitylene 5.17
    ε-caprolactone 38.44
    p-cymene 7.25
    epichlorohydrin 58.84
    1,1,1-trichloroethane 24.44
    2-aminoethanol 23.53
    morpholine-4-carbaldehyde 67.63
    sulfolane 75.72
    2,2,4-trimethylpentane 1.05
    2-methyltetrahydrofuran 27.03
    n-hexyl acetate 14.45
    isooctane 0.87
    2-(2-butoxyethoxy)ethanol 24.92
    sec-butyl acetate 10.19
    tert-butyl acetate 15.2
    decalin 1.05
    glycerin 35.49
    diglyme 48.34
    acrylic acid 40.99
    isopropyl myristate 6.54
    n-butyric acid 35.19
    acetyl acetate 22.04
    di(2-ethylhexyl) phthalate 11.69
    ethyl propionate 12.98
    nitromethane 93.81
    1,2-diethoxyethane 16.05
    benzonitrile 26.21
    trioctyl phosphate 8.62
    1-bromopropane 10.78
    gamma-valerolactone 76.16
    n-decanol 5.7
    triethyl phosphate 13.22
    4-methyl-2-pentanol 6.76
    propionitrile 16.04
    vinylene carbonate 54.16
    1,1,2-trichlorotrifluoroethane 73.18
    DMS 15.17
    cumene 3.56
    2-octanol 6.66
    2-hexanone 11.03
    octyl acetate 9.2
    limonene 8.88
    1,2-dimethoxyethane 31.2
    ethyl orthosilicate 11.83
    tributyl phosphate 9.52
    diacetone alcohol 20.91
    N,N-dimethylaniline 10.12
    acrylonitrile 26.41
    aniline 18.13
    1,3-propanediol 31.92
    bromobenzene 15.67
    dibromomethane 30.35
    1,1,2,2-tetrachloroethane 43.73
    2-methyl-cyclohexyl acetate 15.93
    tetrabutyl urea 12.36
    diisobutyl methanol 7.11
    2-phenylethanol 20.61
    styrene 4.88
    dioctyl adipate 11.36
    dimethyl sulfate 29.55
    ethyl butyrate 16.65
    methyl lactate 25.39
    butyl lactate 18.95
    diethyl carbonate 14.43
    propanediol butyl ether 18.77
    triethyl orthoformate 15.1
    p-tert-butyltoluene 7.32
    methyl 4-tert-butylbenzoate 23.72
    morpholine 33.48
    tert-butylamine 7.06
    n-dodecanol 4.33
    dimethoxymethane 30.01
    ethylene carbonate 38.48
    cyrene 38.01
    2-ethoxyethyl acetate 25.92
    2-ethylhexyl acetate 14.43
    1,2,4-trichlorobenzene 27.01
    4-methylpyridine 26.3
    dibutyl ether 5.73
    2,6-dimethyl-4-heptanol 7.11
    DEF 26.0
    dimethyl isosorbide 40.57
    tetrachloroethylene 36.55
    eugenol 25.27
    triacetin 21.48
    span 80 18.72
    1,4-butanediol 15.48
    1,1-dichloroethane 19.82
    2-methyl-1-pentanol 8.52
    methyl formate 49.27
    2-methyl-1-butanol 10.06
    n-decane 1.12
    butyronitrile 17.82
    3,7-dimethyl-1-octanol 7.41
    1-chlorooctane 4.44
    1-chlorotetradecane 2.15
    n-nonane 0.91
    undecane 0.9
    tert-butylcyclohexane 1.04
    cyclooctane 1.03
    cyclopentanol 20.02
    tetrahydropyran 17.87
    tert-amyl methyl ether 8.97
    2,5,8-trioxanonane 33.83
    1-hexene 1.79
    2-isopropoxyethanol 19.59
    2,2,2-trifluoroethanol 56.09
    methyl butyrate 17.27

    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