Endrin

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  • Identifiers

    CAS number
    72-20-8

    Molecular formula
    C12H8Cl6O

    SMILES
    C1[C@@H]2[C@@H]3[C@H]([C@H]1[C@H]4[C@@H]2O4)[C@@]5(C(=C([C@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 58.79%
    Woody 29.99%
    Balsamic 15.42%
    Burnt 14.98%
    Animal 14.61%
    Dry 14.47%
    Amber 14.09%
    Cooling 13.87%
    Earthy 13.79%
    Spicy 13.75%

     

    Flavor
    Bitter 73.3%
    Odorless 25.26%
    Sweet-like 20.18%
    Bland 18.44%
    Nitrile 18.18%
    Cedarleaf 17.88%
    Oriental 17.44%
    Alkaline 17.37%
    Rotten 17.13%
    Cereal 16.99%

     

    Odor impact est.
    Low

    Odor threshold

    • 1.80x10-2 ppm (perfume/flavor grade purity).

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    2.24 (strong acid)

    Molecular weight
    380.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • Decomposes at 473 °F. (EPA, 1998)
    • Approximately 200 °C (rearranges above that point)
    • 200 °C
    • 473 °F (decomposes)
    • 392 °F (Decomposes)

    Boiling point

    • Decomposes (NTP, 1992)
    • 245 °C (decomposes)
    • Decomposes

    Flash point

    • 37.86 ˚C est.
    • Commercial product may contain flammable liquid with flashpoint 80F. (EPA, 1998)
    • 80 °F (commercial product may contain flammable liquid)

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • Solubility in g/100 ml solvent at 25 °C: acetone 17, benzene 13.8, carbon tetrachloride 3.3, hexane 7.1, and xylene 18.3
    • In water, 0.25 mg/l @ 25 °C
    • Solubility of endrin in fresh water: 200 ug/l.
    • Insol in methanol
    • Solubility in water at 25 °C: none
    • Insoluble

  • Synonyms

    • ENDRIN
    • Nendrin
    • Mendrin
    • Endrin isomer
    • Hexadrin
    • Endrin [ISO]
    • 72-20-8
    • Endrin 20 EC
    • Caswell No. 423
    • Rcra waste number P051
    • Endricol
    • Endrex
    • Oktanex
    • CCRIS 276
    • Latka 269
    • HSDB 198
    • OB9NVE7YCL
    • UNII-OB9NVE7YCL
    • OMS 197
    • EN 57
    • NCI-C00157
    • NSC 8935
    • Compound 269
    • EINECS 200-775-7
    • Endrine
    • Stardrin
    • ENT 17,251
    • EPA Pesticide Chemical Code 041601
    • SD 3419
    • BRN 0091397
    • DTXSID6020561
    • AI3-17251
    • SD 3419 Illoxol
    • Stardrin 20
    • ENDRIN [HSDB]
    • ENDRIN [IARC]
    • ENDRIN [MI]
    • ENDRIN [MART.]
    • Cmpd. 269
    • Experimental insecticide 269
    • Endrin and metabolites
    • 3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth(2,3-b)oxirene
    • (1R,2R,3R,6S,7S,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
    • 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo,endo-1,4:5,8-dimethanonaphthalene
    • DTXCID90196608
    • 4-17-00-00525 (Beilstein Handbook Reference)
    • NSC-8935
    • ENT-17251
    • Hexachloroepoxyoctahydro-endo,endo-dimethanonapthalene
    • (1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth(2,3-b)oxirene
    • (1R,4S,4aS,5S,6S,7R,8R,8aR)-1,2,3,4,10,10-Hexachloro-1,4,4a,5,6,7,8,8a-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
    • 1,2,3,4,10,10-Hexachloro-1R,4S,4aS,5S,6,7R,8R,8aR-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
    • 1,4:5,8-Dimethanonaphthalene, 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-, endo,endo-
    • 2,7:3,6-Dimethanonaphth(2,3-b)oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha)-
    • 3,4,5,6,9,9-Hexachloro-1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha-octahydro-2,7:3,6-dimethanonaphth(2,3-b)oxirene
    • NA 2761
    • SD-3419
    • ENDRIN (IARC)
    • ENDRIN (MART.)
    • Endrine [French]
    • Hexachloroepoxyoctahydro-endo,endo-dimethanonaphthalene
    • (1R,2S,3S,6R,7R,8S,9R,11S)-3,4,5,6,13,13-Hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
    • 2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1a.alpha.,2.beta.,2a.beta.,3.alpha.,6.alpha.,6a.beta.,7.beta.,7a.alpha.)-
    • Latka 269 [Czech]
    • CAS-72-20-8
    • (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene
    • (1AR,2R,2AR,3R,6S,6AS,7S,7AS)-REL-3,4,5,6,9,9-HEXACHLORO-1A,2,2A,3,6,6A,7,7A-OCTAHYDRO-2,7:3,6-DIMETHANONAPHTH(2,3-B)OXIRENE
    • 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,endo-5,8-dimethanonaphthalene
    • 1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-ENDO,ENDO-,1,4:5,8-DIMETHANONAPHTHALENE
    • 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo-1,4-endo-5,8-dimethanonaphthalene
    • 1,2,3,4,10,10-Hexachloro-6,7-Epoxy-1,4,4a,5,6,7,8,8a-octahydro-exo-1,4-exo-5,8-dimethanonaphthalene
    • RCRA waste no. D013
    • RCRA waste no. P051
    • CHEBI:81526
    • Hexacrin
    • ENT 17251
    • NCGC00091352-02
    • (1A ALPHA, 2 BETA, 2A BETA, 3 ALPHA, 6 ALPHA, 6A BETA, 7 BETA, 7A ALPHA)-3,4,5,6,9,9,-HEXACHLORO-1A,2,2A,3,6,6A,7,7A-OCTAHYDRO-2,7:3,6-DIMETHANO-NAPH(2,3-B)OXIRENE
    • (1A ALPHA, 2 BETA, 2A BETA, 3 ALPHA, 6 ALPHA, 6A BETA, 7 BETA, 7A ALPHA)-3,4,5,6,9,9,-HEXACHLORO-1A,2,2A,3,6,6A,7,7A-OCTAHYDRO-2,7:3,6-DIMETHANO-NAPH[2,3-B]OXIRENE
    • (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho(2,3-b)oxirene
    • (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-rel-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene
    • (1R,2S,3R,6S,7R,8S,9S,11R)-3,4,5,6,13,13-Hexachloro-10-oxapentacyclo(6.3.1.1(3,6).0(2,7).0(9,11))tridec-4-ene
    • (1R,2S,3R,6S,7R,8S,9S,11R)-3,4,5,6,13,13-Hexachloro-10-oxapentacyclo[6.3.1.1(3,6).0(2,7).0(9,11)]tridec-4-ene
    • 2,7:3,6-DIMETHANONAPHTH(2,3-B)OXIRENE, 3,4,5,6,9,9-HEXACHLORO-1A,2,2A, 3,6,6A,7,7A-OCTAHYDRO-,(1AALPHA, 2BETA, 2ABETA, 3ALPHA, 6ALPHA, 6ABETA, 7BETA, 7AALPHA)-
    • 2,7:3,6-DIMETHANONAPHTH(2,3-b)OXIRENE, 3,4,5,6,9,9-HEXACHLORO-1a,2,2a,3,6,6a,7,7a-OCTAHYDRO-, (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-rel-
    • 2,7:3,6-DIMETHANONAPHTH[2,3-B]OXIRENE, 3,4,5,6,9,9-HEXACHLORO-1A,2,2A, 3,6,6A,7,7A-OCTAHYDRO-,(1AALPHA, 2BETA, 2ABETA, 3ALPHA, 6ALPHA, 6ABETA, 7BETA, 7AALPHA)-
    • 2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha)-
    • 2,7:3,6-DIMETHANONAPHTH[2,3-b]OXIRENE, 3,4,5,6,9,9-HEXACHLORO-1a,2,2a,3,6,6a,7,7a-OCTAHYDRO-, (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-rel-
    • 3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaph(2,3-b)oxirene
    • 3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaph[2,3-b]oxirene
    • rel-(1aR,2R,2aR,3R,6S,6aS,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho(2,3-b)oxirene
    • rel-(1aR,2R,2aR,3R,6S,6aS,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene
    • ENDRICAL
    • ISODRIN EPOXIDE
    • Endrin (ACGIH:OSHA)
    • Hexachloroepoxyoctahydro-endo, endo-dimethanonaphthalene
    • CHEMBL2356732
    • SCHEMBL21820798
    • Endrin 1000 microg/mL in Hexane
    • Endrin 10 microg/mL in Cyclohexane
    • Endrin 100 microg/mL in Isooctane
    • Tox21_111120
    • Tox21_300613
    • Endrin 10 microg/mL in Acetonitrile
    • NCI 01565
    • NCGC00248106-01
    • NCGC00254373-01
    • H0058
    • NS00066941
    • C00157
    • Q423354
    • 3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth
    • (1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth
    • 1,2,3,4, 10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-ENDO-1,4-ENDO-5,8-DIMETHANONAPHTHALENE
    • 1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-1,4:5,8-ENDO,ENDO-DIMETHANONAPHTHALENE
    • 1,2,3,4,10,10Hexachloro6,7epoxy1,4,4a,5,6,7,8,8aoctahydro1,4endo,endo5,8dimethanonaphthalene
    • 1,4:5,8-DIMETHANONAPHTHALENE, 1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-,ENDO,ENDO-
    • 1,4:5,8-DIMETHANONAPHTHALENE, 1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-ENDO,ENDO-
    • 2,7:3,6-Dimethanonaphth(2,3-b)oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1aR,2R,2aR,3R,6S,6aS,7S,7aS)-rel-
    • 2,7:3,6-DIMETHANONAPHTH(2,3-B)OXIRENE, 3,4,5,6,9,9-HEXACHLORO-1A,2,2A,3,6,6A,7,7A-OCTAHYDRO-, (1AALPHA,2BETA,2ABETA,3AL PHA,6ALPHA,6ABETA,7BETA,7AALPHA)-
    • 2,7:3,6-Dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1aI+/-,2I(2),2aI(2),3I+/-,6I+/-,6aI(2),7I(2),7aI+/-)-
    • 200-775-7
    • 3,4,5,6,9,9-HEXACHLORO-1A,2,2A,3,6,6A,7,7A-OCTAHYDRO-2,7:3,6-DIMETHANO-NAPHTH(2,3-B)OXIRENE
    • 3,4,5,6,9,9-Hexachloro-1aalpha,2beta,2abeta,3alpha,6alpha,6abeta,7beta,7aalpha-octahydro-2,7:3,6-dimethanonaphth

  • Applications

    Endrin (CAS 72-20-8) is a legacy organochlorine insecticide that was historically used in agriculture to protect crops (including cereals, cotton, and fruits) and to safeguard stored products from pest attack; it was also employed in some termite and other public-health pest control programs. Owing to its high toxicity, environmental persistence, and tendency to bioaccumulate, its use is now heavily restricted or banned in many regions, and current practice emphasizes legacy residues, remediation, and strict regulatory controls rather than new applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.8
    methanol 3.25
    isopropanol 1.96
    water 0.04
    ethyl acetate 8.31
    n-propanol 2.82
    acetone 7.09
    n-butanol 3.09
    acetonitrile 4.39
    DMF 18.85
    toluene 10.05
    isobutanol 2.51
    1,4-dioxane 12.3
    methyl acetate 7.4
    THF 23.35
    2-butanone 7.74
    n-pentanol 3.5
    sec-butanol 2.12
    n-hexane 0.51
    ethylene glycol 2.39
    NMP 35.32
    cyclohexane 0.97
    DMSO 8.17
    n-butyl acetate 11.63
    n-octanol 5.83
    chloroform 16.07
    n-propyl acetate 8.56
    acetic acid 5.12
    dichloromethane 13.78
    cyclohexanone 17.0
    propylene glycol 1.98
    isopropyl acetate 8.87
    DMAc 21.5
    2-ethoxyethanol 8.89
    isopentanol 3.84
    n-heptane 1.39
    ethyl formate 6.06
    1,2-dichloroethane 8.7
    n-hexanol 7.06
    2-methoxyethanol 11.86
    isobutyl acetate 8.65
    tetrachloromethane 4.35
    n-pentyl acetate 13.06
    transcutol 22.01
    n-heptanol 6.91
    ethylbenzene 6.24
    MIBK 10.04
    2-propoxyethanol 19.1
    tert-butanol 2.89
    MTBE 4.32
    2-butoxyethanol 15.23
    propionic acid 3.96
    o-xylene 8.27
    formic acid 4.08
    diethyl ether 5.01
    m-xylene 9.03
    p-xylene 7.86
    chlorobenzene 10.42
    dimethyl carbonate 10.49
    n-octane 0.82
    formamide 6.86
    cyclopentanone 22.22
    2-pentanone 9.16
    anisole 11.73
    cyclopentyl methyl ether 13.49
    gamma-butyrolactone 22.13
    1-methoxy-2-propanol 10.16
    pyridine 17.89
    3-pentanone 8.27
    furfural 29.79
    n-dodecane 0.88
    diethylene glycol 14.77
    diisopropyl ether 3.38
    tert-amyl alcohol 2.99
    acetylacetone 14.93
    n-hexadecane 1.04
    acetophenone 15.63
    methyl propionate 9.58
    isopentyl acetate 13.92
    trichloroethylene 20.51
    n-nonanol 6.87
    cyclohexanol 4.92
    benzyl alcohol 10.37
    2-ethylhexanol 7.75
    isooctanol 6.88
    dipropyl ether 7.4
    1,2-dichlorobenzene 12.15
    ethyl lactate 8.01
    propylene carbonate 15.63
    n-methylformamide 8.24
    2-pentanol 2.6
    n-pentane 0.61
    1-propoxy-2-propanol 14.47
    1-methoxy-2-propyl acetate 20.63
    2-(2-methoxypropoxy) propanol 18.27
    mesitylene 6.07
    ε-caprolactone 16.51
    p-cymene 8.25
    epichlorohydrin 23.04
    1,1,1-trichloroethane 9.7
    2-aminoethanol 3.33
    morpholine-4-carbaldehyde 32.11
    sulfolane 26.54
    2,2,4-trimethylpentane 0.68
    2-methyltetrahydrofuran 13.12
    n-hexyl acetate 13.77
    isooctane 0.6
    2-(2-butoxyethoxy)ethanol 19.4
    sec-butyl acetate 7.99
    tert-butyl acetate 11.86
    decalin 1.32
    glycerin 5.0
    diglyme 30.63
    acrylic acid 5.71
    isopropyl myristate 8.97
    n-butyric acid 6.16
    acetyl acetate 8.95
    di(2-ethylhexyl) phthalate 13.07
    ethyl propionate 9.12
    nitromethane 10.75
    1,2-diethoxyethane 11.36
    benzonitrile 13.86
    trioctyl phosphate 9.36
    1-bromopropane 4.82
    gamma-valerolactone 31.4
    n-decanol 5.57
    triethyl phosphate 9.12
    4-methyl-2-pentanol 3.32
    propionitrile 5.23
    vinylene carbonate 16.14
    1,1,2-trichlorotrifluoroethane 23.98
    DMS 14.36
    cumene 5.5
    2-octanol 4.95
    2-hexanone 9.43
    octyl acetate 10.23
    limonene 8.97
    1,2-dimethoxyethane 15.56
    ethyl orthosilicate 9.11
    tributyl phosphate 8.86
    diacetone alcohol 12.52
    N,N-dimethylaniline 12.04
    acrylonitrile 8.18
    aniline 10.17
    1,3-propanediol 4.3
    bromobenzene 11.25
    dibromomethane 8.62
    1,1,2,2-tetrachloroethane 14.64
    2-methyl-cyclohexyl acetate 15.71
    tetrabutyl urea 13.4
    diisobutyl methanol 5.45
    2-phenylethanol 17.47
    styrene 6.35
    dioctyl adipate 12.56
    dimethyl sulfate 14.91
    ethyl butyrate 10.92
    methyl lactate 9.82
    butyl lactate 12.8
    diethyl carbonate 8.52
    propanediol butyl ether 11.57
    triethyl orthoformate 10.66
    p-tert-butyltoluene 8.29
    methyl 4-tert-butylbenzoate 22.48
    morpholine 14.2
    tert-butylamine 2.22
    n-dodecanol 4.54
    dimethoxymethane 17.45
    ethylene carbonate 12.27
    cyrene 25.39
    2-ethoxyethyl acetate 16.82
    2-ethylhexyl acetate 12.62
    1,2,4-trichlorobenzene 15.64
    4-methylpyridine 16.61
    dibutyl ether 5.98
    2,6-dimethyl-4-heptanol 5.45
    DEF 13.38
    dimethyl isosorbide 39.2
    tetrachloroethylene 12.99
    eugenol 24.51
    triacetin 17.1
    span 80 16.12
    1,4-butanediol 2.74
    1,1-dichloroethane 6.44
    2-methyl-1-pentanol 4.4
    methyl formate 8.61
    2-methyl-1-butanol 3.33
    n-decane 1.26
    butyronitrile 5.5
    3,7-dimethyl-1-octanol 7.32
    1-chlorooctane 4.4
    1-chlorotetradecane 2.63
    n-nonane 0.97
    undecane 1.03
    tert-butylcyclohexane 1.19
    cyclooctane 0.76
    cyclopentanol 5.54
    tetrahydropyran 9.09
    tert-amyl methyl ether 5.49
    2,5,8-trioxanonane 26.64
    1-hexene 1.92
    2-isopropoxyethanol 7.94
    2,2,2-trifluoroethanol 5.1
    methyl butyrate 9.89

    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