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Home > Encyclopedia > Chlordene

Chlordene

Chlordene structure

Chlordene 

structure
  • CAS No:

    3734-48-3

  • Formula:

    C10H6Cl6

  • Chemical Name:

    Chlordene

  • Synonyms:

    4,7-Methano-1H-indene,4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-;4,7-Methanoindene,4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-;4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene;Chlordene;4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene;4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene

  • Categories:

    Analytical Chemistry  >  Standard

Chlordene Basic Attributes

338.87

338.87

223-096-8

Y0NOO4CU6D

DTXSID2027545

2903299090

Characteristics

0

5.57

1.73g/cm3

155 °C

357.2ºC at 760 mmHg

100 °C

1.64

In water, 4.62X10-4 mg/L @ 25 deg C

0-6°C

2.0X10-5 mm Hg at 25 deg C /Estimated/

Henry's Law constant = 5.0X10-4 atm-cu m/mol at 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 6.3X10-11 cu cm/mole sec at 25 °C /Estimated/

Safety Information

III

6.1(b)

2761

20-21-23-63

22-36/37/39-45

PC0875000

T

P261-P280-P311

H302-H311 + H331-H361

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

|Danger|H302 (92.68%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Leachate from a 300,000 barrel pesticide waste dump in Hardeman County, TN containing chlordene was identified as the source of chlordene-contamination of private drinking wells in the immediate vicinity(1). The chlordene concentration in the final effluent of an activated sludge waste treatment plant was reported as 47 ug/L(2).

INDOOR: Chlordene was not detected in indoor air of five households with chlordene-contaminated drinking water supplies located in the vicinity of a pesticide waste dump, Hardeman County, TN(1).|RURAL/REMOTE: Chlordene was detected in air samples taken at four different monitoring stations in the arctic, the range was from <0.02-0.32 ppm(1).|SOURCE DOMINATED: Airborne chlordene concentrations in the aeration basin of an activated sludge waste water treatment plant were reported as 1.3, 1.8, 5.9, 21, and 35 ug/L in the grit-chamber weir, grit-chamber drag-out, west end of aeration basin, center of aeration basin, east end of aeration basin, respectively(1). The grit-chamber wastewater effluent concentration was 180 ug/L(1).

Toxicity

Chlordene epoxide is only weakly toxic to houseflies because of its conversion to the Hydroxyepoxide; however, it can be slightly synergized by piperonyl butoxide. /chlordene epoxide/|Epinephrine is contraindicated since it may induce ventricular fibrillation due to the sensition of the myocardium by the chlorinated hydrocarbons. /Chlorinated hydrocarbon insecticides/

LD50 Rat dermal 690 mg/kg

Chlordene's former production and use as a chemical intermediate in the manufacture of the pesticides chlordane and heptachlor(1) resulted in its release into the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 25,000 (SRC), determined from a log Kow of 5.57(2) and a regression-derived equation(3), indicates that chlordene is expected to be immobile in soil(SRC). Volatilization of chlordene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Chlordene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.0X10-5 mm Hg(SRC), determined from a fragment constant method(5). Chlordene has an estimated biodegradation half-life in water on the order of months(6), suggesting biodegradation may not be an important environmental fate process in soil.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 25,000(SRC), determined from a log Kow of 5.57(2) and a regression-derived equation(3), indicates that chlordene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8.6 hrs and 8.3 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 70 months if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3,900(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Chlordene has an estimated biodegradation half-life in water on the order of months(8), suggesting biodegradation may not be an important aqueous environmental fate process.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlordene, which has an estimated vapor pressure of 2.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlordene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.0 hrs(SRC), calculated from its rate constant of 6.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase chlordene may be removed from the air by wet and dry deposition(SRC). Chlordene absorbs light in the environmental UV spectrum and is susceptible to direct photolysis(4).|ATMOSPHERIC FATE: CHLORDENE ALSO UNDERWENT ATMOSPHERIC OXIDATION. CMPD ... /AN EPOXIDE & 1-HYDROXYCHLORDENE/ WERE IDENTIFIED IN RESULTANT MIXTURE OF PRODUCTS.

The rate constant for the vapor-phase reaction of chlordene with photochemically-produced hydroxyl radicals has been estimated as 6.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.0 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A structure estimation method(1) for the reaction of vapor-phase chlordene with ozone provides a rate constant of 20X10-17 cu cm/molecule-sec at 25 °C(SRC). At an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2) the atmospheric half-life of chlordene is estimated to be 1.4 hours. Chlordene concentration in water decreased from 0.057 ppm to 0.022 ppm after 28 days(3); however, hydrolysis is not expected to be a viable biodegradation pathway because of the lack of hydrolyzable functional groups in chlordene. Chlordene absorbs light in the environmental UV spectrum and may be susceptible to direct photolysis(4). Chlordene photolyzed to a photoisomer and unidentified products on irradiation in solution (>280 nm) and by exposure of a thin film to direct sunlight(4).|CHLORDENE WAS ABSORBED ON SILICA GEL & THEN IRRADIATED WITH ULTRA VIOLET LIGHT ... CHLORDENE REQUIRED 1.5 HR FOR 50% CONVERSION ... PRODUCTS INCLUDED: CHLORDENE EPOXIDE, PHOTOCHLORDENE, 1-EXO-HYDROXY CHLORDENE, KETOCHLORDENE, UNIDENTIFIED CMPD & POLAR & POLYMER MATERIAL. WHEN QUARTZ WAS USED INSTEAD OF PYREX, HEPTACHLOR WAS ... OBTAINED.|RATES OF CONVERSION & DEGRADATION OF CHLORDENE ARE INFLUENCED BY PHOTOLYSIS & CHEMICAL HYDROLYSIS. RELATIVE BALANCE OF EPOXIDATION, INTOXICATION, HYDROXYLATION, AND DETOXICATION DETERMINES MAGNITUDE OF PERSISTING RESIDUES IN ENVIRONMENT.

An estimated BCF of 3,900 was calculated for chlordene(SRC), using a log Kow of 5.57(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not altered physically or chemically once released into the environment.

The Koc of chlordene is estimated as 25,000(SRC), using a log Kow of 5.57(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chlordene is expected to be immobile in soil.

The Henry's Law constant for chlordene is estimated as 5.0X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chlordene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 8.6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 8.3 days(SRC). Chlordene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 70 months when adsorption is considered(3). The potential for volatilization of chlordene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 2.0X10-5 mm Hg(SRC), determined from a fragment constant method(4).|The objective of this research was to investigate some of the potentially controlling factors influencing the atmospheric releases of volatile organic chlorinated cmpd from the activated-sludge sewage treatment process. The field study was designed to evaluate the wastewater and airborne concn of 6 chlorinated cmpd: hexachlorobicycloheptadiene, (hex-VCL), chlordene, trichloromethane, carbontetrachloride and tetrachloroethylene. The highest wastewater concentrations for the water-insoluble hexachlorobicycloheptadiene, hex-VCL, and chlordene were found in the aeration basins. The aerial release of these water-insoluble cmpd was enhanced by increased aeration rate but depressed by higher suspended solids concentrations.

DRINKING WATER: Chlordene was detected in five of twenty-four private drinking water wells serving residents in Toone-Teague area, Hardeman County, TN, located in the vicinity of a pesticide waste dump at a concentration range of trace to 0.81 ug/L(1).|SURFACE WATER: Chlordene was detected at <0.1 ppm in Mississippi River samples taken at the Carrolton Water Plant in New Orleans(1).|... CYCLODIENES IDENTIFIED IN USA DRINKING WATER INCL ... CHLORDENE ... .

Chlordene was not detected in any of 234 food items analyzed as part of an April 1982 total U.S. Diet study conducted by the US FDA(1). The compound was detected in one sample of one food type at a concentration of 0.0007 ug/g as part of the overall Market Basket Survey conducted from 1982 to 1991(2). Chlordene was present in the edible portion of catfish after environmental exposure(3).

Occupational exposure and general population exposure should be low since chlordene is no longer produced or used. In the past, chlordene was applied directly to the soil as a pesticide and exposure to this compound was primarily during production, application and at water treatment facilities(SRC). Worker exposure to chlordene was probable in activated-sludge wastewater treatment plants, as shown by concentrations of 2.2 and 53 ug/cu m, upwind and downwind, respectively, from contact aeration basins(1).

Chlordene was not detected in human adipose tissue during a study of 92 subjects (49 females) in six Canadian municipalities(1).|Human breast adipose tissues were examined for 13 components and metabolites of technical chlordane. The geometric mean concentrations of heptachlor epoxide, oxychlordane, and trans-nonachlor were 48, 88, and 120 ng/g of fat, respectively. These concentrations increased with the subject's age, but were not much different from 1970-1980 values. The nanochlors and the pentachlorocyclopentene chlordanes are the most highly retained compounds in people, when compared to their abundances in technical people was compared to its accumulation in other mammals, in fishes, and in invertebrates by using a calculated parent/metabolite ratio. The sources of chlordane exposure were evaluated, and it was concluded that exposure to chlordane in indoor air was an important source of these components to the USA population.

Drug Information

...Chlorinated cyclodienes... are efficiently absorbed through the skin. /Chlorinated Cyclodiene insecticides/|Organochlorines are well absorbed from the lung, gastrointestinal tract, and skin. /Organochlorines/|The chief route of excretion is biliary, although nearly all organochlorines yield measurable urinary metabolites. ... Many of the unmetabolized pesticides are efficiently reabsorbed by the intestine (enterohepatic circulation) substantially retarding fecal excretion. /Solid organochlorine insecticides/

Hepatic mixed function oxidase ... was investigated. When chlordene was used as substrate, hydroxylation preceded epoxidation. With preparations from the kissing gourami (helostoma sp) and pigeon, 1-hydroxy-2,3-epoxychlordene formed after the epoxide.|A 3-day aquatic system was used to evaluate uptake and biotransformation of chlordene ... chlordene epoxide, 1-hydroxychlordene, 1-hydroxychlordene epoxide and a polar metabolite /were formed in/ oedogonium, physa, culex and gambusia. Two unknowns /were formed in/ physa and gambusia.|Chlorodene metabolism ... studies with salt marsh caterpillar, estigmane acrea, and sheep liver microsomes ... /yielded/ chlordene epoxide, 1-hydroxychlordene, 1-hydroxychlordene epoxide, 2 unknowns and 1 polar metabolite. Sheep liver microsomes /yielded/ 1 unknown not found in salt marsh caterpillar.|Houseflies converted chlordene into an epoxide and two compounds identified as 1-hydroxychlordene and the 1-hydroxy epoxide. ... When incubated with pig liver microsomes, chlordene epoxide was converted into a diol.|For more Metabolism/Metabolites (Complete) data for CHLORDENE (8 total), please visit the HSDB record page.

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in theevent of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. ... /Organochlorine insecticides/|In cases of ingestion, ... Oil-based cathartics such as castor oil or other substances including fats or oils should be avoided since these compounds may tend to enhance the absorption of the chlorinated hydrocarbon from the gastrointestinal tract. Convulsions may be treated with diazepam ... administered intravenously ... . Methods to enhance elimination have not been successful other than as a supportive measure for hepatic and renal failure. /Chlorinated hydrocarbon insecticides/|Seizures, hypoxemia, and resultant acidosis are the immediate life-threatening emergencies. Diazepam is the anticonvulsant of choice. Moderately to severely poisoned patients should have intravenous lines and a cardiac monitor. ...Experimental animal studies suggest that chlorinated hydrocarbon pesticide absorption by charcoal is highly variable. Most organochlorine insectcides contain organic solvents, which are severe aspiration hazards. Skin decontamination (removal of contaminated clothes, washing of area with water and green or mild soap) is necessary to prevent continued dermal absorption. Be careful not to cross-contaminate health personnel. The use of cholestyramine (3-8 g four times a day) increased fecal excretion of chlordecone by seven times and reduced the mean blood half-life from 165 to 80 days. In organochlorine exposures to compounds that have substantial enterohepatic recirculation, activated charcoal also may reduce the half-life and should be considered in serial doses for moderate to severe acute poisonings. Dialysis, diuresis, and hemoperfusion are ineffective because of extensive tissue binding and large volumes of distribution. /Organochlorines/|Treatment: 1. perform gastric lavage with tap water (unless convulsions are imminent). 2. Sodium sulfate catharsis... . Avoid oil laxatives. 3. A rapidly acting barbiturate or diazepam may aid in controlling convulsions, but care must be taken not to augment any respiratory depression. 4. Oxygen therapy and artificial ventilation may be necessary. 5. Avoid epinephrine. 6. Since no specific antidotes are known, symptomatic therapy must be accompanied by complete rest. 7. Use soap and water in adequate quantities to wash off any compound spilled on the skin. If spilled in eyes, wash repeatedly with water. /Chlordane/|For more Antidote and Emergency Treatment (Complete) data for CHLORDENE (8 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ The chlorinated cyclodiene insecticides are among the most toxic and environmentally persistent pesticides known. ...Even at low doses, these chemicals tend to induce convulsions before less serious signs of illness occur. Although the sequence of signs generally follows the appearance of headaches, nausea, vertigo, and mild clonic jerking, motor hyperexcitability, and hyperreflexia, some patients have convulsions without warning symptoms. ...Chronic exposure to low or moderate concentrations of these agents elicits a spectrum of signs and symptoms, involving both sensory and motor components of the CNS. /Chlorinated cyclodiene insecticides/|/SIGNS AND SYMPTOMS/ ... Symptoms of poisoning result from stimulation of CNS and include headache, blurred vision, dizziness, slight involuntary muscular movements, sweating, insomnia, bad dreams, nausea, and general malaise. More severe illness is characterized by jerking of muscles or groups of muscles and epileptiform convulsions, with loss of consciousness, involuntary incontinence of urine and feces, disorientation, personality changes, psychic disturbances, and loss of memory. Such seizures may recur for 2-4 months after cessation of exposure and are marked by abnormal encephalographic patterns. /Cyclodiene insecticides/|/SIGNS AND SYMPTOMS/ Organochlorines are CNS stimulators that produce apprehension, excitability, paresthesias, dizziness, headache, disorientation, and tremor progressing to stupor, coma, and convulsions in severe cases. Organochlorines may enhance myocardial irritability, leading to cardiac dysrhythmias after heavy exposures. Serious complications involve seizures with resultant hypoxemia, severe metabolic acidosis, and death. Intoxication from acute oral exposures generally begins within 45 minutes to several hours. Subacute toxicity has been reported after the extensive and careless use of ... /organochlorines/ over several weeks. Symptoms included paresthesias, anorexia, nausea, fatigue, and malaise. /Organochlorines/|/OTHER TOXICITY INFORMATION/ The chief acute toxic action of the organochlorine pesticides is on the central nervous system, where these compounds interfere with fluxes of cations across nerve cell membranes, increasing neuronal irritability. This effect is manifest mainly as convulsions, sometimes limited to myoclonic jerking, but often expressed as violent seizures. ... Convulsions may cause death by interfering with pulmonary gas exchange and by generating severe metabolic acidosis. Various disturbances of sensation, coordination, and mental function are also characteristic of acute organochlorine poisoning. High tissue concentrations of organochlorines increase myocardial irritability, predioposing to cardiac arrhythmias. When tissue organochlorine concentrations drop below threshold levels, recovery from the poisoning occurs. Organochlorines are not cholinesterase inhibitors. /Solid organochlorine insecticides/

chlordene

Chlordene Use and Manufacturing

Uses

INTERMEDIATE IN MFR OF CHLORDANE & HEPTACHLOR.

4,7-Methano-1H-indene, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-: INACTIVE|MFR BY CONDENSING HEXACHLOROCYCLOPENTADIENE, MADE BY CHLORINATING PENTANES: US PATENT 2,509,160, OR CYCLOPENTADIENE: US PATENT 2,606,910, WITH CYCLOPENTADIENE TO PRODUCE CHLORDENE ... .|A new method is developed to synthesize chlordene. Cyclopentadiene and sodium hypochlorite are reacted at 20-40 °C. The reaction product is collected from the liquid phase and reacted with cyclopentadiene. The reaction product is then chlorinated to obtain chlordene.|CYCLODIENE INSECTICIDES ARE HIGHLY CHLORINATED CYCLIC HYDROCARBONS WITH ENDOMETHYLENE BRIDGED STRUCTURES PREPARED BY DIELS-ALDER DIENE REACTION. DEVELOPMENT OF THESE MATERIALS RESULTED FROM HYMAN'S DISCOVERY IN 1945 OF CHLORDENE, THE ADDUCT OF HEXACHLOROCYCLOPENTADIENE & CYCLOPENTADIENE.|CHLORDENE IS AN INTERMEDIATE IN PRODUCTION OF THE INSECTICIDE CHLORDANE, & IS A MINOR CONSTITUENT OF LOW INSECTICIDAL ACTIVITY IN TECHNICAL CHLORDANE.|Termite-control agents are dispersed or dissolved in lubrication oils containing anionic and nonionic surfactants to yield a preparation having a high penetration rate into wood. A composition containing chlordene 50, polyoxyethylene alkylphenol ether-calcium dodecylbenzenesulfonate mixture 10, and lubricating oil 40% is given as an example.

A method was developed to make a quantity of photoheptachlor-ketone available for identification of possible residues as well as for toxicological and metabolic studies. Heptachlor and chlordene are, respectively, hydrolyzed and metabolized to l-hydroxychlordene, which may be metabolically or chemically oxidized to l-ketochlordene, which may be photoisomerized to photoheptachlorketone. l-Hydroxychlordene is prepared synthetically from chlordene or by refluxing with silver carbonate in aqueous ethanol. l-Hydroxychlordene is oxidized to l-ketochlordene using activated manganese dioxide as the oxidant. A mixture of sodium dichromate, acetic acid, and water may also be used as an oxidant. This reagant is simple and gives good yields.

Computed Properties

Molecular Weight:338.9
XLogP3:4.2
Exact Mass:337.857116
Monoisotopic Mass:335.860066
Heavy Atom Count:16
Complexity:439
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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