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Inherent Properties, Identifiers and References
ChemSpider ID: 2940
Empirical Formula: C12H8Cl6O
Molecular Weight: 380.9093
Nominal Mass: 378 Da
Average Mass: 380.9093 Da
Monoisotopic Mass: 377.870631 Da
Quick Links: Permalink Similar Isomers
Systematic Name:
SMILES: Cl\C1=C(/Cl)C2(Cl)C3C4CC(C3C1(Cl)C2(Cl)Cl)C5OC45
InChI: InChI=1/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15​)12(11,17)18/h2-7H,1H2
InChIKey: DFBKLUNHFCTMDC-UHFFFAOYAM
(Details...) Wikipedia Article(s)
Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. The molecule has a ring structure based on naphthalene. Dieldrin is closely related to aldrin which itself breaks down to form dieldrin. Aldrin is not toxic to insects, it is oxidised in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene. Originally developed in the 1940s as an alternative to DDT, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin is a stereoisomer of dieldrin. However, it is an extremely persistent organic pollutant, it does not easily break down. Furthermore it tends to biomagnify as it is passed along the food chain. Long-term exposure has proven toxic to a very wide range of animals including humans, far greater than to the original insect targets. For this reason it is now banned in most of the world. It has been linked to health problems such as Parkinson's, Breast Cancer, and immune, reproductive, and nervous system damage. It can also adversly affect testicular descent in the fetus if a pregnant woman is exposed to Dieldrin. Read more... or Edit at Wikipedia...
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User Data

  • miscellaneous
    • Appearance: Colorless to tan, crystalline solid with a mild, chemical odor. [insecticide]
    • Appearance: Colorless to light-tan crystals with a mild, chemical odor. [insecticide]
    • Appearance: white or beige crystalline solid
    • Appearance: white or light brown powder or crystals
    • Stability: Stable. Incompatible with strong acids, strong oxidizers. Corrodes some metals.
    • Stability: Stable. Breakdown product of aldrin in the environment. Incompatiblewith acids, active metals and strong oxidizing agents.
    • Toxicity: Ingestion of 1 mg kg-1 may cause harmful effects. Note low LD50s below. CNS, ORL-RAT LD50 3 mg kg-1, SKN-RAT LD50 12 mg kg-1, ORL-MKY LD50 3 mg kg-1, ORL-RBT LD50 7 mg kg-1, ORL-GPG LD50 16 mg kg -1
    • Toxicity: ORL-RAT LD50 38 mg kg-1, SKN-RAT LD50 56 mg kg-1, SCU-RAT LD50 49 mg kg-1, IVN-RAT LD50 9 mg kg-1, ORL-MKY LD50 3 mg kg-1, ORL-BWD LD50 13 mg kg-1
    • Safety: Use and manufacture of this compound have been phased outin many countries. It accumulates in the environment and has beenfound in human milk. It should not be used unless no alternative isavailable, and then only after a full risk assessment has been prepared.
    • Safety: Safety glasses, gloves, good ventilation.
    • Symptoms: Epileptiform convulsions; stupor, headache, dizziness; abdominal discomfort, nausea, vomiting; insomnia; aggressiveness, confusion; drowsiness, lassitude (weakness, exhaustion); anorexia; in animals: liver damage
    • Symptoms: Headache, dizziness; nausea, vomiting, malaise (vague feeling of discomfort), sweating; myoclonic limb jerks; clonic, tonic convulsions; coma; [potential occupational carcinogen]; in animals: liver, k idney damage
    • Target Organs: central nervous system, liver
    • Target Organs: central nervous system, liver, kidneys, skin Cancer Site [in animals: lung, liver, thyroid & adrenal gland tumors]
    • Incompatibilities and Reactivities: Strong oxidizers, strong acids, parathion [Note: May emit hydrogen chloride & phosgene when heated or burned.]
    • Incompatibilities and Reactivities: Strong oxidizers, active metals such as sodium, strong acids, phenols
    • Personal protection and Sanitation: Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated Remove: When wet or contaminated Change: Daily Provide: Eyewash, Quick drench
    • Personal protection and Sanitation: Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated/Daily Remove: When wet or contaminated Change: Daily Provide: Eyewash, Quick drench
    • Exposure Limits: NIOSH REL : TWA 0.1 mg/m 3 [skin] OSHA PEL : TWA 0.1 mg/m 3 [skin]
    • Exposure Limits: NIOSH REL : Ca TWA 0.25 mg/m 3 [skin] See Appendix A OSHA PEL : TWA 0.25 mg/m 3 [skin]
    • Source: synthetic
  • experimental physchem properties
    • Melting Point: ca. 200 C (decomposes)
    • Melting Point: 176 C
    • Boiling Point: 385 C
    • Specific Gravity: 1.70
    • Specific Gravity: 1.75
    • Solubility: Insoluble
    • Solubility: 0.02%
    • Vapor Pressure: Low
Names and Synonyms

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(1aa,2b,2​aa,3b,6b,​6aa,7b,7a​a)-3,4,5,​6,9,9-Hex​achloro-1​a,2,2a,3,​6,6a,7,7a​-octahydr​o-2,7:3,6​-dimethan​onaphth[2​,3-b]oxir​ene

1,2,3,4,1​0,10-hexa​chloro-6,​7-epoxy-1​,4,4a,5,6​,7,8,8a-o​ctahydro-​endo,endo​-1,4:5,8-​dimethano​naphthale​ne

1,2,3,4,1​0,10-Hexa​chloro-6,​7-epoxy-1​,4,4a,5,6​,7,8,8a-o​ctahydro-​endo,exo-​1,4:5,8-d​imethanon​aphthalene

1,4:5,8-D​imethanon​aphthalen​e, 1,2,3,​4,10,10-h​exachloro​-6,7-epox​y-1,4,4a,​5,6,7,8,8​a-octahyd​ro-

1,4:5,8-D​imethanon​aphthalen​e, 1,2,3,​4,10,10-h​exachloro​-6,7-epox​y-1,4,4a,​5,6,7,8,8​a-octahyd​ro-, endo​,endo-

1,4:5,8-D​imethanon​aphthalen​e, 1,2,3,​4,10,10-h​exachloro​-6,7-epox​y-1,4,4a,​5,6,7,8,8​a-octahyd​ro, endo,​exo-

1,4:5,8-D​imethanon​aphthalen​e, 1,2,3,​4,10,10-h​exachloro​-6,7-epox​y-1,4,4a,​5,6,7,8,8​a-octahyd​ro-, endo​,exo-

1,8,9,10,​11,11-Hex​achloro-4​,5-exo-ep​oxy-2,3-7​,6-endo-2​,1-7,8-ex​o-tetracy​clo[6.2.1​.13,6.02,​7]dodec-9​-ene

2,7:3,6-D​imethanon​aphth[2,3​-b]oxiren​e, 3,4,5,​6,9,9-hex​achloro-1​a,2,2a,3,​6,6a,7,7a​-octahydr​o-

200-484-5 [EINECS/ELINCS]

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Database ID(s)

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(Details...) Predicted Properties
LogP: ACD/LogP: 4.88
XLogP: 3.00
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 4.88 ACD/LogD (pH 7.4): 4.88
ACD/BCF (pH 5.5): 3003.73 ACD/BCF (pH 7.4): 3003.73
ACD/KOC (pH 5.5): 10737.53 ACD/KOC (pH 7.4): 10737.53
#H bond acceptors: 1 #H bond donors: 0
#Freely Rotating Bonds: 0 Polar Surface Area: 12.53 Å2
Index of Refraction: 1.676 Molar Refractivity: 77.48 cm3
Molar Volume: 205.9 cm3 Polarizability: 30.71 10-24cm3
Surface Tension: 60.2 dyne/cm Density: 1.84 g/cm3
Flash Point: 155.3 °C Enthalpy of Vaporization: 64.34 kJ/mol
Boiling Point: 416.2 °C at 760 mmHg Vapour Pressure: 9.43E-07 mmHg at 25°C
MeSH
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  5.45
    Log Kow (Exper. database match) =  5.40
       Exper. Ref:  DeBruijn,J et al. (1989)
    Log Kow (Exper. database match) =  5.20
       Exper. Ref:  DeBruijn,J et al. (1989)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  340.17  (Adapted Stein & Brown method)
    Melting Pt (deg C):  135.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.74E-006  (Modified Grain method)
    MP  (exp database):  226-230 deg C
    BP  (exp database):  330 deg C
    VP  (exp database):  3.00E-06 mm Hg at 20 deg C
    Subcooled liquid VP: 0.000292 mm Hg (20 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.1455
       log Kow used: 5.20 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  0.195 mg/L (25 deg C)
        Exper. Ref:  BIGGAR,JW & RIGGS,RI (1974)
     Water Sol (Exper. database match) =  0.25 mg/L (25 deg C)
        Exper. Ref:  BIGGAR,JW & RIGGS,RI (1974)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.022128 mg/L
    Wat Sol (Exper. database match) =  0.20
       Exper. Ref:  BIGGAR,JW & RIGGS,RI (1974)
    Wat Sol (Exper. database match) =  0.25
       Exper. Ref:  BIGGAR,JW & RIGGS,RI (1974)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Epoxides
       Vinyl/Allyl Halides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.41E-007  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 1.00E-05  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  9.438E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.20  (exp database)
  Log Kaw used:  -3.585  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  8.785
      Log Koa (experimental database):  8.130

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.0013
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   0.6733  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.2245  (months      )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1158
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3951
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.0389 Pa (0.000292 mm Hg)
  Log Koa (Exp database): 8.130
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.71E-005 
       Octanol/air (Koa) model:  3.31E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00278 
       Mackay model           :  0.00613 
       Octanol/air (Koa) model:  0.00264 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  10.0856 E-12 cm3/molecule-sec
      Half-Life =     1.061 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    12.726 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.003579 E-17 cm3/molecule-sec
      Half-Life =   320.239 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.00445 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.06E+004
      Log Koc:  4.025 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Ka (acid-catalyzed) at 25 deg C :  1.713E-002  L/mol-sec
  Ka Half-Life at pH 7:      12.823  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 3.304 (BCF = 2014)
       log Kow used: 5.20 (expkow database)

 Volatilization from Water:
    Henry LC:  1E-005 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River:      116.3  hours   (4.844 days)
    Half-Life from Model Lake :       1432  hours   (59.66 days)

 Removal In Wastewater Treatment:
    Total removal:              83.13  percent
    Total biodegradation:        0.71  percent
    Total sludge adsorption:    82.35  percent
    Total to Air:                0.07  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.148           25.4         1000       
   Water     3.61            4.32e+003    1000       
   Soil      69.2            8.64e+003    1000       
   Sediment  27.1            3.89e+004    0          
     Persistence Time: 6.14e+003 hr
(Details...) SimBioSys LASSO