Coumaphos

Overview IFRA Request a quote

  • Identifiers

    CAS number
    56-72-4

    Molecular formula
    C14H16ClO5PS

    SMILES
    CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(=C(C(=O)O2)Cl)C

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 53.61%
    Grape 27.29%
    Floral 24.46%
    Roasted 23.11%
    Meaty 22.1%
    Savory 20.8%
    Cooked 20.32%
    Animal 18.71%
    Fruity 18.5%
    Milky 18.47%

     

    Flavor
    Bitter 58.46%
    Odorless 32.14%
    Mild 26.63%
    Fruity 25.04%
    Bland 24.56%
    Parsley 20.33%
    Orange blossom 20.18%
    Orange flower 20.07%
    Ethyl benzoate 19.72%
    Taco 19.72%

     

    Odor impact est.
    Low

    Odor threshold

    • 2.0X10-2 ppm (Detection in water; purity not specified).

  • Properties

    XLogP3-AA
    4.5

    pKa est.
    4.75 (weak acid)

    Molecular weight
    362.8 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 196 °F (EPA, 1998)
    • 95.2 °C
    • MP: 90-92 °C (technical coumaphos)
    • 91 °C
    • 196 °F

    Boiling point

    • 68 °F at 1e-07 mmHg (NTP, 1992)
    • 68 °F at 1x10-7 mmHg

    Flash point

    • 194.31 ˚C est.
    • Not Applicable. Combustible solid. (USCG, 1999)

    Solubility expt.

    • less than 1 mg/mL at 72 °F (NTP, 1992)
    • In water, 1.5 mg/L at 20 °C
    • Limited solubility in organic solvents
    • Somewhat soluble in acetone, chloroform, corn oil
    • At 20 °C, soluble in acetone (23.82 g/100 mL) and diethyl phthalate (21.50 g/100 mL); much less soluble in denatured alcohol and xylene (0.9 g/100 mL in each); only slightly soluble in octanol (0.13 g/100 mL), hexane (0.07 g/100 mL), and mineral spirits (0.09 g/100 mL)
    • Solubility in water: none

  • Synonyms

    • COUMAPHOS
    • 56-72-4
    • Coumafos
    • Asuntol
    • Asunthol
    • Meldane
    • Muscatox
    • Resitox
    • Baymix
    • Azunthol
    • Agridip
    • Meldone
    • Suntol
    • CO-Ral
    • Cumafos
    • Baymix 50
    • 3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester
    • Diolice
    • Negashunt
    • Umbethion
    • Bayer 21/199
    • Cumafosum
    • Negasunt
    • Bayer 21199
    • NCI-C08662
    • Coumafosum
    • Resistox
    • 3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate
    • BAY 21/199
    • ENT 17,957
    • O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphate
    • O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioate
    • OMS 485
    • 3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate
    • Phosphorothioic acid, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl ester
    • 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin
    • DTXSID2020347
    • o-(3-Chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) o,o-diethyl phosphorothioate
    • Coumarin, 3-chloro-7-hydroxy-4-methyl-, O-ester with O,O-diethyl phosphorothioate
    • O-3-Chloro-4-methyl-7-coumarinyl O,O-diethyl phosphorothioate
    • Diethyl 3-chloro-4-methylumbelliferyl thionophosphate
    • NSC-8944
    • L08SZ5Z5JC
    • O-(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphate
    • O,O-Diethyl O-(3-chloro-4-methylcoumarinyl-7) thiophosphate
    • O,O-Diethyl O-(3-chloro-4-methylumbelliferyl)phosphorothioate
    • O,O-Diethyl O-(3-chloro-4-methyl-7-coumarinyl)phosphorothioate
    • BAYER-21199
    • 3-Chloro-4-methylumbelliferone O-ester with O,O-diethyl phosphorothioate
    • Diethyl thiophosphoric acid ester of 3-chloro-4-methyl-7-hydroxycoumarin
    • O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-benzopyran-7-yl)phosphorothioate
    • 3-Chloro-7-hydroxy-4-methyl-coumarin O-ester with O,O-diethyl phosphorothioate
    • O,O-Diaethyl-O-(3-chlor-4-methyl-cumarin-7-yl)-monothiophosphat
    • Thiophosphate de O,O-diethyle et de O-(3-chloro-4-methyl-7-coumarinyle)
    • DTXCID20347
    • Phosphorothioic acid, O,O-diethyl ester, O-ester with 3-chloro-7-hydroxy-4-methylcoumarin
    • CHEBI:3903
    • O,O-Diethyl O-(3-chloro-4-methylumbelliferone) thiophosphate
    • O,O-Dietil-O-(3-cloro-4-metil-cumarin-7-il-monotiofosfato)
    • O,O-Diethyl-O-(3-chloor-4-methyl-cumarin-7-yl)monothiofosfaat
    • O-(3-Chloro-4-methyl-7-coumarinyl) O,O-diethylphosphorothioate
    • O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2h-benzopyran-7-yl) phosphorothioate
    • O-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate
    • O-(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl phosphorothioate
    • Meldane 2
    • RefChem:58640
    • 200-285-3
    • coumophos
    • Coumaphos [ISO]
    • C14H16ClO5PS
    • Coumaphoscumafos
    • Coumafos [INN]
    • 3-chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one
    • NSC8944
    • Coumafos (INN)
    • NCGC00094516-01
    • 3-chloro-7-diethoxyphosphinothioyloxy-4-methyl-chromen-2-one
    • Cumafos [Dutch]
    • Caswell No. 335
    • O,O-Dietil-O-(3-chloro-4-metil-cumarin-7-il-monotiofosfato)
    • Cumafos [INN-Spanish]
    • O,O-Diethyl-O-(3-chloro-4-methyl-cumarin-7-yl)monothiofosfaat
    • Coumafosum [INN-Latin]
    • CAS-56-72-4
    • CCRIS 180
    • HSDB 249
    • NSC 8944
    • EINECS 200-285-3
    • UNII-L08SZ5Z5JC
    • EPA Pesticide Chemical Code 036501
    • BRN 0327083
    • Perizin
    • Koral
    • AI3-17957
    • Coumaphos D10 di(ethyl-D5) 100 microg/mL in Acetonitrile
    • Meldane (TN)
    • Co-ral (phosphate)
    • Spectrum_001767
    • Diethyl-O-(3-chloro-4-methyl-7-coumarinyl) phosphorothioate
    • SpecPlus_000350
    • COUMAPHOS [MI]
    • COUMAPHOS [HSDB]
    • Spectrum2_001845
    • Spectrum3_000805
    • Spectrum4_000645
    • Spectrum5_001924
    • COUMAFOS [MART.]
    • O,O-Diethyl-O-(3-chloor-4-methyl-cumarin-7-yl)monothiofosfaat [Dutch]
    • O,O-Dietil-O-(3-cloro-4-metil-cumarin-7-il-monotiofosfato) [Italian]
    • O,O-Diaethyl-O-(3-chlor-4-methyl-cumarin-7-yl)-monothiophosphat [German]
    • Thiophosphate de O,O-diethyle et de O-(3-chloro-4-methyl-7-coumarinyle) [French]
    • BSPBio_002269
    • KBioGR_000989
    • KBioSS_002248
    • SPECTRUM330012
    • 4-18-00-00344 (Beilstein Handbook Reference)
    • MLS002695922
    • DivK1c_006446
    • SCHEMBL120173
    • SPBio_001630
    • COUMAPHOS [GREEN BOOK]
    • CHEMBL251680
    • SCHEMBL29363459
    • KBio1_001390
    • KBio2_002247
    • KBio2_004815
    • KBio2_007383
    • 56-72-4

  • Applications

    Coumaphos (CAS 56-72-4) is an organophosphate chemical primarily used as an external parasiticide for livestock, including cattle, swine, and poultry, applied in dips, sprays, or pour-on formulations to control external parasites such as mites, lice, and ticks; it is also used as a miticide in beekeeping to control Varroa destructor in honey bee colonies; in industrial settings, it can serve as an intermediate or building block in the synthesis of other organophosphate pesticides; in laboratory and regulatory contexts, coumaphos may be used as a reference material or analytical standard for residue analysis to support monitoring of pesticide residues in animal-derived foods; its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.9
    methanol 22.12
    isopropanol 11.49
    water 0.1
    ethyl acetate 29.55
    n-propanol 16.79
    acetone 55.98
    n-butanol 14.87
    acetonitrile 28.7
    DMF 213.01
    toluene 9.57
    isobutanol 11.62
    1,4-dioxane 52.66
    methyl acetate 36.2
    THF 88.86
    2-butanone 46.35
    n-pentanol 16.05
    sec-butanol 13.53
    n-hexane 0.41
    ethylene glycol 8.23
    NMP 170.87
    cyclohexane 0.98
    DMSO 135.16
    n-butyl acetate 24.57
    n-octanol 7.7
    chloroform 73.3
    n-propyl acetate 28.45
    acetic acid 40.14
    dichloromethane 100.27
    cyclohexanone 71.46
    propylene glycol 9.39
    isopropyl acetate 18.43
    DMAc 160.47
    2-ethoxyethanol 46.48
    isopentanol 11.82
    n-heptane 0.74
    ethyl formate 33.34
    1,2-dichloroethane 65.07
    n-hexanol 11.17
    2-methoxyethanol 70.5
    isobutyl acetate 15.72
    tetrachloromethane 4.19
    n-pentyl acetate 27.93
    transcutol 62.14
    n-heptanol 8.77
    ethylbenzene 5.12
    MIBK 19.62
    2-propoxyethanol 46.38
    tert-butanol 11.75
    MTBE 9.68
    2-butoxyethanol 27.69
    propionic acid 25.43
    o-xylene 6.16
    formic acid 24.24
    diethyl ether 14.23
    m-xylene 5.97
    p-xylene 8.25
    chlorobenzene 26.18
    dimethyl carbonate 30.36
    n-octane 0.55
    formamide 50.39
    cyclopentanone 89.79
    2-pentanone 34.51
    anisole 20.13
    cyclopentyl methyl ether 25.8
    gamma-butyrolactone 111.48
    1-methoxy-2-propanol 45.04
    pyridine 65.77
    3-pentanone 30.2
    furfural 120.56
    n-dodecane 0.66
    diethylene glycol 42.37
    diisopropyl ether 3.5
    tert-amyl alcohol 11.88
    acetylacetone 54.99
    n-hexadecane 0.79
    acetophenone 33.94
    methyl propionate 34.14
    isopentyl acetate 20.03
    trichloroethylene 122.48
    n-nonanol 8.53
    cyclohexanol 14.91
    benzyl alcohol 26.97
    2-ethylhexanol 8.57
    isooctanol 7.88
    dipropyl ether 10.93
    1,2-dichlorobenzene 26.43
    ethyl lactate 21.71
    propylene carbonate 54.42
    n-methylformamide 73.46
    2-pentanol 8.75
    n-pentane 0.54
    1-propoxy-2-propanol 31.95
    1-methoxy-2-propyl acetate 35.4
    2-(2-methoxypropoxy) propanol 31.71
    mesitylene 3.29
    ε-caprolactone 59.09
    p-cymene 5.97
    epichlorohydrin 124.81
    1,1,1-trichloroethane 26.31
    2-aminoethanol 14.63
    morpholine-4-carbaldehyde 146.28
    sulfolane 143.56
    2,2,4-trimethylpentane 0.41
    2-methyltetrahydrofuran 39.59
    n-hexyl acetate 22.76
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 35.52
    sec-butyl acetate 15.3
    tert-butyl acetate 18.08
    decalin 0.68
    glycerin 21.62
    diglyme 66.0
    acrylic acid 31.65
    isopropyl myristate 11.24
    n-butyric acid 29.23
    acetyl acetate 23.8
    di(2-ethylhexyl) phthalate 17.91
    ethyl propionate 23.49
    nitromethane 102.23
    1,2-diethoxyethane 32.0
    benzonitrile 35.87
    trioctyl phosphate 11.2
    1-bromopropane 19.22
    gamma-valerolactone 146.9
    n-decanol 7.0
    triethyl phosphate 15.28
    4-methyl-2-pentanol 5.37
    propionitrile 26.45
    vinylene carbonate 60.68
    1,1,2-trichlorotrifluoroethane 82.46
    DMS 28.61
    cumene 3.97
    2-octanol 7.08
    2-hexanone 29.4
    octyl acetate 14.9
    limonene 7.71
    1,2-dimethoxyethane 77.78
    ethyl orthosilicate 13.74
    tributyl phosphate 13.54
    diacetone alcohol 28.76
    N,N-dimethylaniline 15.83
    acrylonitrile 45.51
    aniline 20.2
    1,3-propanediol 21.78
    bromobenzene 23.16
    dibromomethane 47.41
    1,1,2,2-tetrachloroethane 84.14
    2-methyl-cyclohexyl acetate 21.21
    tetrabutyl urea 23.0
    diisobutyl methanol 5.5
    2-phenylethanol 24.63
    styrene 7.5
    dioctyl adipate 19.99
    dimethyl sulfate 54.61
    ethyl butyrate 22.02
    methyl lactate 31.89
    butyl lactate 25.33
    diethyl carbonate 17.56
    propanediol butyl ether 22.43
    triethyl orthoformate 18.25
    p-tert-butyltoluene 5.22
    methyl 4-tert-butylbenzoate 32.29
    morpholine 61.74
    tert-butylamine 5.29
    n-dodecanol 5.59
    dimethoxymethane 82.33
    ethylene carbonate 46.35
    cyrene 53.16
    2-ethoxyethyl acetate 46.06
    2-ethylhexyl acetate 16.47
    1,2,4-trichlorobenzene 33.5
    4-methylpyridine 52.9
    dibutyl ether 10.1
    2,6-dimethyl-4-heptanol 5.5
    DEF 61.01
    dimethyl isosorbide 65.34
    tetrachloroethylene 45.22
    eugenol 38.13
    triacetin 36.16
    span 80 26.43
    1,4-butanediol 14.6
    1,1-dichloroethane 32.74
    2-methyl-1-pentanol 13.22
    methyl formate 59.45
    2-methyl-1-butanol 12.07
    n-decane 0.95
    butyronitrile 23.78
    3,7-dimethyl-1-octanol 8.07
    1-chlorooctane 5.51
    1-chlorotetradecane 2.81
    n-nonane 0.75
    undecane 0.78
    tert-butylcyclohexane 0.51
    cyclooctane 0.36
    cyclopentanol 22.22
    tetrahydropyran 27.79
    tert-amyl methyl ether 9.78
    2,5,8-trioxanonane 52.93
    1-hexene 2.82
    2-isopropoxyethanol 27.96
    2,2,2-trifluoroethanol 24.56
    methyl butyrate 33.34

    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