Ethion

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  • Identifiers

    CAS number
    563-12-2

    Molecular formula
    C9H22O4P2S4

    SMILES
    CCOP(=S)(OCC)SCSP(=S)(OCC)OCC

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sulfurous 56.31%
    Onion 40.63%
    Meaty 39.52%
    Savory 34.74%
    Roasted 34.21%
    Fresh 29.55%
    Garlic 28.69%
    Cooked 27.62%
    Alliaceous 26.43%
    Tropical 25.87%

     

    Flavor
    Sulfurous 36.77%
    Sulfury 35.94%
    Onion 35.63%
    Cabbage 32.37%
    Cooked 30.74%
    Fruity 28.84%
    Meaty 28.78%
    Garlic 27.46%
    Roasted 27.3%
    Vegetable 24.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.1

    pKa est.
    1.58 (strong acid)

    Molecular weight
    384.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • 9 to 10 °F (EPA, 1998)
    • -12 to -13 °C
    • -12 - -13 °C
    • 9-10 °F
    • 10 °F

    Boiling point

    • Decomposes above 302.0 °F (USCG, 1999)
    • 165 °C @ 0.3 mm Hg
    • BP: decomposes >150 °C
    • >302 °F (decomposes)
    • >302 °F (Decomposes)

    Flash point

    • 178.02 ˚C est.
    • 349 °F (NIOSH, 2024)
    • 349 °F

    Solubility expt.

    • 0.0001 % (NIOSH, 2024)
    • Soluble in xylene, chloroform, acetone, kerosene, and 1% methyl ethyl ketone or benzene, and methylated naphthalene.
    • Sol in petroleum oils, most organic solvents
    • Sol in methyl alcohol and ethyl alcohol
    • MISCIBLE WITH AROMATICS
    • In water, 2.0 mg/l @ 25 °C
    • Solubility in water, g/100ml at 20 °C: 0.0001
    • 0.0001%

  • Synonyms

    • ethion
    • 563-12-2
    • Diethion
    • Ethanox
    • Ethopaz
    • Nialate
    • Embathion
    • Ethodan
    • Hylemox
    • Rhodocide
    • Rodocid
    • Phosphotox E
    • Fosfatox E
    • Niagara 1240
    • Fosfono 50
    • Vegfru fosmite
    • Ethiol 100
    • KWIT
    • Ethiol
    • RP 8167
    • Ethyl methylene phosphorodithioate
    • Bis(S-(diethoxyphosphinothioyl)mercapto)methane
    • FMC-1240
    • NIA 1240
    • S,S'-Methylene bis(O,O-diethyl phosphorodithioate)
    • Hylemax
    • Rodocide
    • Itopaz
    • ENT 24,105
    • Vegfru-fosmite
    • RP-Thion
    • O,O,O',O'-Tetraethyl S,S'-methylenebis(phosphorodithioate)
    • 2TI07NO12Y
    • DTXSID2024086
    • CHEBI:38663
    • Phosphorodithioic acid, S,S'-methylene O,O,O',O'-tetraethyl ester
    • O,O,O',O'-Tetraaethyl-bis(dithiophosphat)
    • Tetraethyl S,S'-methylene bis(phosphorothiolothionate)
    • O,O,O',O'-Tetraethyl S,S'-methylenebisphosphordithioate
    • S,S'-Methylene O,O,O',O'-tetraethyl phosphorodithioate
    • ETHION [HSDB]
    • O,O,O',O'-Tetraethyl-S,S'-methylenebisphosphorodithioate
    • ETHION [ISO]
    • Methyleen-S,S'-bis(O,O-diethyl-dithiofosfaat)
    • ETHION [MI]
    • ETHION [MART.]
    • o,o,o',o'-tetraethyl s,s'-methylene bis(phosphorodithioate)
    • Methylene-S,S'-bis(O,O-diaethyl-dithiophosphat)
    • O,O,O',O'-Tetraaethyl-bis(dithiophosphat) [German]
    • Phosphorodithioic acid, O,O-diethyl ester, S,S-diester with methanedithiol
    • O,O,O,O-Tetraethyl S,S'-methylenebis(dithiophosphate)
    • Methyleen-S,S'-bis(O,O-diethyl-dithiofosfaat) [Dutch]
    • DTXCID204086
    • Methylene-S,S'-bis(O,O-diaethyl-dithiophosphat) [German]
    • O,O,O',O'-Tetraethyl S,S'-Methylene bisphosphorodithioate
    • O,O,O',O'-Tetraethyl S,S'-methylene di(phosphorodithioate)
    • S,S'-Methylen-bis(O,O-diaethyl-dithiophosphat)
    • O,O,O',O'-tetraethyl S,S'-methanediyl bis(dithiophosphate)
    • O,O,O',O'-tetraethyl S,S'-methanediyl bis(phosphorodithioate)
    • ETHION (MART.)
    • Caswell No. 427
    • Ethyl methylene phosphorodithioate ([(EtO)2P(S)S]2CH2)
    • O,O,O',O'-tetraethyl S,S'-methylene bis(dithiophosphate)
    • O,O,O',O'-Tetraethyl-S,S'-methylene di(phosphorodithioate)
    • Ethion [ANSI:BSI:ISO]
    • HSDB 399
    • EINECS 209-242-3
    • EPA Pesticide Chemical Code 058401
    • BRN 1804530
    • O,O,O',O'-TETRAAETHYL-BIS(DITHIOPHOSPHAT) (GERMAN)
    • UNII-2TI07NO12Y
    • Rhodiacide
    • ETHYL METHYLENE PHOSPHORODITHIOATE (((ETO)2P(S)S)2CH2)
    • METHYLEEN-S,S'-BIS(O,O-DIETHYL-DITHIOFOSFAAT) (DUTCH)
    • Ethion solution
    • AI3-24105
    • METHYLENE-S,S'-BIS(O,O-DIAETHYL-DITHIOPHOSPHAT) (GERMAN)
    • O,O-diethyl ((((diethoxy(sulfanylidene)-lambda5-phosphanyl)sulfanyl)methyl)sulfanyl)phosphonothioate
    • O,O-diethyl [({[diethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}methyl)sulfanyl]phosphonothioate
    • Ethion (ACGIH)
    • S,S'-Methylen-bis(O,O-diaethyl-dithiophosphat) [German]
    • Spectrum_001765
    • 'Cethion' (Cheminova)
    • SpecPlus_000346
    • Spectrum2_001225
    • Spectrum3_000803
    • Spectrum4_000643
    • Spectrum5_001923
    • Rhodocide (Rhone-Poulenc)
    • Ethion, analytical standard
    • 'Ethiol' (Rhone-Poulenc)
    • SCHEMBL26750
    • BSPBio_002265
    • KBioGR_000985
    • KBioSS_002246
    • 4-01-00-03093 (Beilstein Handbook Reference)
    • MLS002695987
    • BIDD:ER0160
    • DivK1c_006442
    • SPBio_001070
    • CHEMBL1713417
    • KBio1_001386
    • KBio2_002245
    • KBio2_004813
    • KBio2_007381
    • KBio3_001765
    • RIZMRRKBZQXFOY-UHFFFAOYSA-
    • FMC1240
    • HMS3091A24
    • S,S'-Methylene O,O,O',O'-tetraethyl di(phosphorodithioate)
    • Ethion 1000 microg/mL in Acetone
    • Ethion 10 microg/mL in Cyclohexane
    • Tox21_300175
    • CCG-39131
    • Ethion 10 microg/mL in Acetonitrile
    • NIA 12 40
    • Ethion 100 microg/mL in Cyclohexane
    • USEPA/OPP PC Code 058401.
    • AKOS015962063
    • FE41188
    • diethoxyphosphinothioylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-lambda5-phosphane
    • NCGC00163850-01
    • NCGC00163850-02
    • NCGC00163850-03
    • NCGC00254044-01
    • O,O,O',O'Tetraaethylbis(dithiophosphat)
    • AC-15695
    • CAS-563-12-2

  • Applications

    Ethion (CAS 563-12-2) is an organophosphate insecticide primarily used in agriculture and horticulture to protect crops from a broad range of pests. It is formulated as emulsifiable concentrates (EC) or granules and applied to crops such as cereals, fruits, and vegetables to control field pests; it is also used for stored-product pest control in warehouses under local regulatory conditions; it supports integrated pest management (IPM) programs as an approved tool within regulated use patterns; and it can be employed in controlled environments such as greenhouses where permitted by regulation. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 63.06
    methanol 72.93
    isopropanol 46.95
    water 1.38
    ethyl acetate 295.9
    n-propanol 64.92
    acetone 378.91
    n-butanol 56.98
    acetonitrile 229.86
    DMF 1129.76
    toluene 135.71
    isobutanol 48.97
    1,4-dioxane 290.34
    methyl acetate 314.89
    THF 554.19
    2-butanone 304.58
    n-pentanol 53.32
    sec-butanol 60.21
    n-hexane 12.56
    ethylene glycol 30.75
    NMP 1508.12
    cyclohexane 32.35
    DMSO 914.21
    n-butyl acetate 229.8
    n-octanol 46.32
    chloroform 897.05
    n-propyl acetate 217.03
    acetic acid 284.93
    dichloromethane 924.55
    cyclohexanone 548.95
    propylene glycol 38.2
    isopropyl acetate 195.09
    DMAc 1023.88
    2-ethoxyethanol 162.56
    isopentanol 51.17
    n-heptane 18.7
    ethyl formate 239.83
    1,2-dichloroethane 503.16
    n-hexanol 60.09
    2-methoxyethanol 223.88
    isobutyl acetate 128.79
    tetrachloromethane 133.27
    n-pentyl acetate 199.21
    transcutol 279.79
    n-heptanol 46.1
    ethylbenzene 74.77
    MIBK 153.69
    2-propoxyethanol 173.54
    tert-butanol 64.59
    MTBE 136.22
    2-butoxyethanol 123.69
    propionic acid 172.57
    o-xylene 119.62
    formic acid 143.08
    diethyl ether 154.4
    m-xylene 104.12
    p-xylene 99.77
    chlorobenzene 306.8
    dimethyl carbonate 266.46
    n-octane 9.72
    formamide 277.68
    cyclopentanone 740.54
    2-pentanone 251.01
    anisole 198.69
    cyclopentyl methyl ether 305.46
    gamma-butyrolactone 920.92
    1-methoxy-2-propanol 171.53
    pyridine 414.29
    3-pentanone 272.21
    furfural 1019.48
    n-dodecane 7.92
    diethylene glycol 127.71
    diisopropyl ether 59.85
    tert-amyl alcohol 79.01
    acetylacetone 458.43
    n-hexadecane 9.34
    acetophenone 308.32
    methyl propionate 310.49
    isopentyl acetate 183.83
    trichloroethylene 1256.58
    n-nonanol 48.62
    cyclohexanol 103.51
    benzyl alcohol 149.33
    2-ethylhexanol 64.31
    isooctanol 43.34
    dipropyl ether 125.07
    1,2-dichlorobenzene 381.25
    ethyl lactate 134.83
    propylene carbonate 513.43
    n-methylformamide 389.46
    2-pentanol 46.29
    n-pentane 14.55
    1-propoxy-2-propanol 150.77
    1-methoxy-2-propyl acetate 293.06
    2-(2-methoxypropoxy) propanol 156.57
    mesitylene 74.26
    ε-caprolactone 503.05
    p-cymene 79.43
    epichlorohydrin 776.14
    1,1,1-trichloroethane 468.55
    2-aminoethanol 55.14
    morpholine-4-carbaldehyde 956.99
    sulfolane 1468.34
    2,2,4-trimethylpentane 13.29
    2-methyltetrahydrofuran 367.65
    n-hexyl acetate 190.88
    isooctane 6.93
    2-(2-butoxyethoxy)ethanol 151.62
    sec-butyl acetate 150.48
    tert-butyl acetate 212.16
    decalin 20.36
    glycerin 88.56
    diglyme 363.93
    acrylic acid 229.75
    isopropyl myristate 84.38
    n-butyric acid 191.06
    acetyl acetate 307.59
    di(2-ethylhexyl) phthalate 99.9
    ethyl propionate 216.79
    nitromethane 982.54
    1,2-diethoxyethane 183.31
    benzonitrile 267.23
    trioctyl phosphate 70.17
    1-bromopropane 198.04
    gamma-valerolactone 1007.88
    n-decanol 38.19
    triethyl phosphate 165.38
    4-methyl-2-pentanol 32.7
    propionitrile 159.46
    vinylene carbonate 580.13
    1,1,2-trichlorotrifluoroethane 692.92
    DMS 288.97
    cumene 55.76
    2-octanol 38.25
    2-hexanone 185.78
    octyl acetate 106.88
    limonene 120.67
    1,2-dimethoxyethane 327.81
    ethyl orthosilicate 140.82
    tributyl phosphate 97.38
    diacetone alcohol 182.57
    N,N-dimethylaniline 184.63
    acrylonitrile 276.06
    aniline 158.79
    1,3-propanediol 71.8
    bromobenzene 347.17
    dibromomethane 513.34
    1,1,2,2-tetrachloroethane 845.86
    2-methyl-cyclohexyl acetate 196.73
    tetrabutyl urea 150.88
    diisobutyl methanol 45.65
    2-phenylethanol 142.51
    styrene 103.37
    dioctyl adipate 152.0
    dimethyl sulfate 692.42
    ethyl butyrate 220.91
    methyl lactate 195.27
    butyl lactate 146.48
    diethyl carbonate 177.25
    propanediol butyl ether 94.94
    triethyl orthoformate 178.1
    p-tert-butyltoluene 81.58
    methyl 4-tert-butylbenzoate 260.12
    morpholine 336.93
    tert-butylamine 41.61
    n-dodecanol 31.26
    dimethoxymethane 406.5
    ethylene carbonate 409.98
    cyrene 305.79
    2-ethoxyethyl acetate 289.23
    2-ethylhexyl acetate 178.39
    1,2,4-trichlorobenzene 474.24
    4-methylpyridine 421.96
    dibutyl ether 84.01
    2,6-dimethyl-4-heptanol 45.65
    DEF 468.55
    dimethyl isosorbide 392.87
    tetrachloroethylene 496.94
    eugenol 206.5
    triacetin 313.62
    span 80 140.52
    1,4-butanediol 43.26
    1,1-dichloroethane 352.09
    2-methyl-1-pentanol 55.08
    methyl formate 380.36
    2-methyl-1-butanol 58.87
    n-decane 13.18
    butyronitrile 145.54
    3,7-dimethyl-1-octanol 50.48
    1-chlorooctane 60.05
    1-chlorotetradecane 28.17
    n-nonane 11.59
    undecane 9.79
    tert-butylcyclohexane 16.18
    cyclooctane 15.35
    cyclopentanol 143.09
    tetrahydropyran 260.5
    tert-amyl methyl ether 152.94
    2,5,8-trioxanonane 260.28
    1-hexene 39.9
    2-isopropoxyethanol 122.87
    2,2,2-trifluoroethanol 232.87
    methyl butyrate 269.07

    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