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highest concentration of HCCPD. The concentration at that time found in kidneys was 8 times higher compared to the liver. When given oral doses, the concentration in blood peaked at 4 hours after ingestion. The general distribution pattern stayed the same as the concentration found in the liver was 30â40% of what was found in the liver. Opposite results are found for mice. In mice the concentration in the liver is found to be higher than in the kidney after oral ingestion. The amount of HCCPD in the kidneys was between 33â50% of that in the liver.
1133:. Workers noticed a strange odor on the plant and even a blue haze after a heavy rain. When some of them sought medical attention, it was determined the plant was contaminated with HCCPD, and numerous tests were performed to document these circumstances. Approximately one fifth of waste water treatment workers reported having nausea and abdominal cramps after exposure for a period between 3 and 15 days. They also reported respiratory complaints like sore throats, coughing and breathing difficulty. However, tests on lung function and chest
39:
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674:. Velsicol knows the dangers of handling HCCPD and therefore requires its buyers to go through a strict review and educational program on the storage, use and disposal of the chemical. The company also provides safety data sheets and a handling guide on its website, and delivers the chemical to purchasers all over the world. Of the Chinese company less is known. It is said to be a company specialized in chloro-alkali and
1009:. In order to see degenerative brain effects in for example rats, the animals are exposed to a high dose of HCCPD concentration by inhalation. When dealing with low exposure levels, HCCPD reactivity makes the chance of reactive species in the blood at high concentrations very low. However, at higher doses the probability of transporting reactive material across the
989:
damage done might only become apparent in a later stage of life. Absorption may differ for children because of their incompletely developed organs and larger surface to body weight ratio. Fortunately, it is very unlikely that small children are immediately exposed to HCCPD because it is only found as an impurity in pesticides and is not used in homes.
514:
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ranged were achieved in 10 to 30 days. The liver reached the steady state concentration in 30 days. At this time the concentration of HCCPD was roughly half of what was found in the kidneys. In mice, steady state in reproductive and fat tissue was reached in 20 days. At this time, the amount of HCCPD
1173:
For prolonged exposure, significant differences occur between lab animal species. Where all mice died in the first week in a 13-week study, being exposed to 2 ppm HCCPD for 5 days a week, 6 hours a day, rats however survived until the third week. For a very low exposure of 0.04 ppm, 3 out of 20 mice
609:
hypochlorite and after fractional distillation has a yield of about 75%, the other 25% consists of lower chlorinated cyclopentadienes. The second process uses thermal dechlorination, which occurs at 470-480 °C and gives a yield higher than 90%. Therefore, the first process is easier to perform,
988:
are probably more susceptible to adverse effects than the general population. Another group that is particularly vulnerable to hazardous chemicals is children. In their development there are critical periods where distinct structures and functions can be more susceptible towards disruption, and the
958:
Humans exposed to HCCPD do not show adverse health effects exclusive to that chemical. A small percentage of wastewater treatment workers who were exposed to water containing HCCPD in 1977 reported irritation of skin and eyes, chest discomfort, headaches, nausea and fatigue. In the long term, they
861:
HCCPD. In rats, the route of absorption appeared to have a significant effect on the degree of absorption. The low levels in blood might indicate poor gastrointestinal absorption. Generally, the site of uptake shows the highest concentration in animals. In inhalation studies, the lungs showed the
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and skin. Overall the levels of HCCPD in blood were lower when administered through food compared to when inhalation was used. This may indicate a poor absorption in the gastrointestinal tract due to binding to the gastrointestinal contents. When HCCPD is absorbed, it is distributed to the liver,
665:
Besides manufacturers that produce the chemical for scientific synthesis and reference, there are two companies that produce HCCPD for industrial use: Velsicol
Chemical LLC in the United States and Jiangsu Anpon Electrochemicals Co. in China. The first produces the chemical on a large scale to be
1128:
There is data for human exposure to HCCPD for numerous organ systems. Waste water treatment plant and water cleanup crew workers were exposed after industrial release of the compound into the environment. The initial concentration of the compound in air was unknown but was later determined to be
1083:
were observed. The dose had a direct relationship to the severity of these effects. This and the location suggests that these effects result from direct contact of the tissue with HCCPD. Body weight was heavily affected after oral ingestion of HCCPD by rats, more severely for males than females.
1058:
appeared after a single non lethal dose after 21 days. Lower doses in rats caused no observable tissue changes in the lungs. High doses created degenerative changes to the heart as well. Again, low doses resulted in no observable change in heart tissue. Also, these rats and rabbits experienced
971:, but none were deemed significant enough. Experiments performed on laboratory animals like rats and mice show that a yellow-brown pigment forms in the epithelium of the nose after long-term inhalation exposure, even at low doses, which is considered a useful biomarker for long-term exposure.
796:. This reaction is used to produce pesticides such as Aldrin (named after the reaction) and Isodrin. Most of these pesticides are no longer commercially available and banned by the Stockholm convention on persistent organic pollutants due to their toxicity to humans and animals.
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of the animals can be affected by the concentration and duration of HCCPD exposure. From all the animals tested, guinea pigs showed to be the most resistant to the compound toxicity. Almost all biological systems are shown to be vulnerable to the toxicity of HCCPD, except the
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in the other. In addition, some of the potential metabolites such as hexachloro-2-cyclopentanone, hexachloro-3-cyclopentanone, hexachloroindone, or octachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene-1,8-dione were not yet identified by extraction of excreted material.
1119:
HCCPD is highly toxic to animals when inhaling its vapours. No human studies regarding lethality were done, but there has been an incident involving a waste water treatment centre where humans were exposed, from which most relevant human information is taken.
1041:
Single doses of HCCPD were found to be moderately toxic to animals if ingested orally. However, as the compound was not entirely pure (93.3%) while performing studies, some of the toxic effects could be attributed to the impurities, especially at high doses.
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EPA. 1984. Health effects assessment for hexachlorocyclopentadiene. Cincinnati, OH: U.S. Environmental
Protection Agency, Office of Research and Development, Office of Health and Environmental Assessment, Environmental Criteria and Assessment Office.
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died and none of the rats died. Chronic exposure of HCCPD at very low concentrations produced a yellow-brown pigment in the lung, tracheal and nasal epithelium in rats and mice. The pigmentation did not disappear after the exposure stopped.
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such as lungs and the liver, people can be more susceptible to HCCPD exposure because of their already compromised organ function. Because respiratory exposure seems to be the most prevalent route of exposure, people suffering from
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might indicate damage to heart, as well as to the liver. No evidence of heart function impairment was found in both worker groups though. The elevated levels in patients diminished after a period of 3 weeks.
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Data of oral effects on other species that mice and rats are limited. Single high doses of HCCPD resulted in increased effort to breathe in rats and rabbits alike. The lung tissues of these animals were
1231:
in 1955 and extensive commercialization. However, due to extensive use, the HCCPD family of insecticides (chlordane, aldrin, dieldrin, endrin, heptachlor) became less effective as a result of
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blood and fluid by exposure of HCCPD (93,3% pure, so again a possibility of contaminant interference). Other effects regarding organs with dermal dose were degenerative changes in the heart,
816:
are prominent pathways. The figure below gives an indication of possible degradation pathways when HCCPD is released into the environment. Light, water and oxygen can cause a double bond to
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of rabbits, guinea pigs and monkeys. Damage to the skin could be seen, namely discolored and inflamed skin. When the animals did not die by these lesions, they healed over time by itself.
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kidney and lungs. The organ with the highest concentration differs when comparing rats and mice. The highest concentration in rats is found in the kidney versus in the liver of mice.
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levels. However, these irregularities could be due to many other compounds and variations in health. Other proposed parameters for characterizing effects in humans, like urinary
581:, although commercial samples appear lemon-yellow liquid sometimes with a bluish vapour. Many of its derivatives proved to be highly controversial, as studies showed them to be
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reaction. This might then explain why HCCPD causes effects at the point of contact for all the possible routes of exposure, in addition to the tissue-binding properties.
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There is a slight difference in ratios of the amount excreted in urine and the amount excreted in feces between rats and mice. Though generally, the highest portion of
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1297:. However, given that HCCPD is a versatile raw material for the synthesis of a wide range of end products, as of October 2021 it is still available commercially.
905:
of HCCPD is not known. There are contradicting results from different studies regarding the composition of excreted material. The metabolites were found to be
291:
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and also in wires and cables, due to its good moisture resistance. In the meantime, scientific research has also demonstrated its impact on the environment
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Kominsky JR, Wisseman CL, Morse DL. 1980. Hexachlorocyclopentadiene contamination of a municipal wastewater treatment plant. Am Ind Hyg Assoc J 415.52-556
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For acute high exposures (1 hour, 42 ppm) all animals died, after showing difficulty breathing and gasping for air. Their lung tissues showed hemorrhagic
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was found in 11 out of 41 workers from the wastewater treatment. These levels was not nearly as high for workers from the water cleanup crew, but the
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adducts of HCCPD were developed with a number of cyclic dienes. Some of these compounds gained commercial attention such as the adduct of HCCPD with
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tissue degeneration was observed for acute inhalation. The same tissue degeneration was observed for longer experiments with lower concentrations.
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Increasing dermal doses showed a shorter survival time for the animals. Lung effects of rabbits were examined in dermal animal studies, showing
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Today, almost all HCCPD derivatives have been banned or are under consideration for banning, according to the deliberations of the
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is the most common reaction route, with a degradation half-life of 2 to 4 minutes. Deeper under water where less light penetrates
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The form in which HCCPD appears in the environment, so in its pure form or in solution, showed a striking effect on the
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of humans in relation to HCCPD. It was however tested on animals and is postulated to have effects on brain and
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reactions in 1930. The HCCPD chemical family quickly attracted increased attention with the discovery of its
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did not show any abnormalities. Workers exposed to HCCPD for a longer time reported respiratory irritation,
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585:. An estimated 270,000 tons were produced until 1976, and smaller amounts continue to be produced today.
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congestion, most likely because of direct contact of these tissues with HCCPD from the air, and not as a
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1380:
Dieter Hönicke, Ringo Födisch, Peter Claus, Michael Olson (2002). "Cyclopentadiene and
Cyclopentene".
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1270:. This development raised concern and the use of Mirex was completely discontinued. Before this,
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if HCCPD is inhaled. Furthermore, the highest portion of radiolabeled molecules is recovered in
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synthetically, it is possible that the HCCPD could react directly with cellular alkenes in a
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function seemed not be impaired after exposure of HCCPD in rats, mice and monkeys. Moderate
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1197:. However recovery of the animals that survived was apparent 2 weeks after the treatment.
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study in rats, the approximate distribution of HCCPD in the tissues remained the same.
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in the kidney was approximately half of the concentration found in the liver. In an
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1262:. In the 1970s, it was shown that the Mirex dimer degrades in the environment into
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1254:â or âBox dimerâ and was offered commercially as a flame retardant to be used in
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HCCPD is a highly toxic organochlorine compound that was first mentioned as a
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to give 1,1,2,3,4,5-octachlorocyclopentane, which in a second step undergoes
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of the targeted insects. The number of insects resistant to cyclodienes and
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HCCP is electrophilic. It degrades in base. Alcoholysis affords ketals C
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and operating as a subsidiary of China
National Agrochemical Corporation.
17:
1632:"Hexachlorocyclopentadiene: Versatile Intermediate for Multiple End-Uses"
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Gassman, P. G.; Marshall, J. L. (1968). "7,7-Dimethoxybicycloheptene".
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showed irregularities in their liver function using tests that monitor
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Except where otherwise noted, data are given for materials in their
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Later, in 1957, another use of the compound was found, namely as a
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that were commercialized as pesticides. The main derivatives are:
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When there is pre-existing damage to organs involved in uptake or
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2: Seymour, R.B; Deanin, R.D; History of
Polymeric Composites;
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levels were elevated for 12 out of 97 of these workers. These
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after single oral dosages of HCCPD, and showed acute necrotic
844:
HCCPD absorption in the body occurs mostly through the lungs,
574:
1480:"Toxicological Profile for Hexachlorocyclopentadiene (HCCPD)"
1005:. In the brain, HCCPD or a metabolite thereof can react with
681:
In addition, Hexachlorocyclopentadiene readily undergoes the
1512:"Company Overview of Jiangsu Anpon Electrochemical Co., Ltd"
225:
46:
37:
1494:"Hexachlorocyclopentadiene | Velsicol Chemical, LLC"
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McBee; Baranauckas
Industrial and Engineering Chemistry;
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excretion, were also tested for their potential use as a
1595:"Hexachlorocyclopentadiene Safety Data Sheet, Version 5"
1498:
Hexachlorocyclopentadiene | Velsicol
Chemical, LLC
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for polyesters. In addition, HCCPD was used to make a
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U.S. Department of Health and Human services (1999).
1329:
National
Institute for Occupational Safety and Health
1295:
Stockholm
Convention on Persistent Organic Pollutants
553:), also known as C-56, Graphlox, and HRS 1655, is an
1071:. In repeated exposure experiments on rats and mice
828:and form pentachlorodienoic acid, which forms two
733:from cyclopentadiene, followed by monochlorination
1104:and degenerative changes of the adrenal glands.
187:
857:The relevant absorption studies are done using
99:
1383:Ullmann's Encyclopedia of Industrial Chemistry
1348:Ullmann's Encyclopedia of Industrial Chemistry
1634:. Velsicol Chemical Corporation. October 2021
1600:. Velsicol Chemical Corporation. January 2019
890:is limited as apparently less than 1% of the
8:
1414:: CS1 maint: multiple names: authors list (
1345:Robert L. Metcalf (2002). "Insect Control".
1020:to mice, rats, rabbits and guinea pigs. The
724:, followed by cyclopentadiene, followed by
610:but the second gives a more pure product.
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70:1,2,3,4,5,5-hexachlorocyclopenta-1,3-diene
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836:. However, this is only a minor pathway.
593:Hexachlorocyclopentadiene is prepared by
265:InChI=1S/C5Cl6/c6-1-2(7)4(9)5(10,11)3(1)8
207:
1323:NIOSH Pocket Guide to Chemical Hazards.
1016:Short-term inhalation of HCCPD is
275:InChI=1/C5Cl6/c6-1-2(7)4(9)5(10,11)3(1)8
1429:Production of hexachlorocyclopentadiene
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449:100 °C (212 °F; 373 K)
392:239 °C (462 °F; 512 K)
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382:â10 °C (14 °F; 263 K)
268:Key: VUNCWTMEJYMOOR-UHFFFAOYSA-N
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352:Pale-yellow to amber-colored liquid
1282:. This flame retardant was used in
1054:after a given dose. Extensive lung
901:The exact pathway for the complete
278:Key: VUNCWTMEJYMOOR-UHFFFAOYAM
178:
1553:"Stockholm Convention - Home page"
917:As the compound readily undergoes
753:, followed by esterification with
299:ClC1(Cl)C(/Cl)=C(/Cl)\C(\Cl)=C1\Cl
78:graphlox, perchlorocyclopentadiene
25:
1278:, which was sold under the name
1250:. This dimer was also known as â
1152:In addition, elevated levels of
512:
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508:(at 25 °C , 100 kPa).
1129:ranging between 0.27 and 0.97
426:Occupational safety and health
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945:if HCCPD is orally ingested.
583:persistent organic pollutants
459:(US health exposure limits):
997:No studies were done on the
937:metabolites is recovered in
832:species with the release of
867:steady state concentrations
605:: The first procedure uses
33:
1680:
1158:aspartate aminotransferase
714:, followed by chlorination
704:is a metabolite of aldrin)
28:Hexachlorocyclopentadiene
1239:approached 300 by 1989.
1169:Animal inhalation effects
547:Hexachlorocyclopentadiene
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1124:Human inhalation effects
949:Indications (biomarkers)
743:followed by chlorination
589:Synthesis and production
485:TWA 0.01 ppm (0.1 mg/m)
1386:. Weinheim: Wiley-VCH.
1351:. Weinheim: Wiley-VCH.
1229:insecticidal properties
788:HCCP readily undergoes
565:. It is a precursor to
555:organochlorine compound
404:0.0002% (Reacts, 25°C)
1077:epithelial hyperplasia
975:Unusual susceptibility
846:gastrointestinal tract
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1266:, a well established
919:DielsâAlder reactions
685:to give a variety of
577:. It is a colourless
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1154:lactic dehydrogenase
683:Diels-Alder reaction
362:Pungent, unpleasant
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1011:blood-brain barrier
886:of the compound to
751:cis-butene-1,4-diol
603:dehydrochlorination
399:Solubility in water
344: g·mol
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1276:1,5-cyclooctadiene
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993:Effects on animals
804:In surface water,
557:with the formula C
535:Infobox references
494:(Immediate danger)
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543:Chemical compound
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700:(the related
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676:agrochemicals
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1557:www.pops.int
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1183:inflammation
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1073:inflammation
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1037:Oral effects
1015:
996:
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957:
935:radiolabeled
932:
916:
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894:is found in
881:
864:
859:radiolabeled
856:
843:
826:ring-opening
803:
787:
772:
741:dihydrofuran
680:
664:
595:chlorination
592:
550:
546:
545:
455:
435:Main hazards
424:
372:1.702 g/cm3
84:Identifiers
76:Other names
1284:polyolefins
1272:Diels-Alder
1225:Diels-Alder
1223:in certain
1081:forestomach
1069:forestomach
1013:is higher.
872:intravenous
790:Diels-Alder
726:epoxidation
445:Flash point
429:(OHS/OSH):
349:Appearance
308:Properties
163:100.000.937
1653:Categories
1638:2021-10-01
1604:2021-10-01
1527:Org. Synth
1435:, 41; p806
1301:References
1268:carcinogen
1056:hemorrhage
981:metabolism
903:metabolism
892:radiolabel
853:Absorption
820:to give a
810:hydrolysis
806:photolysis
763:dienochlor
747:endosulfan
731:heptachlor
672:pesticides
567:pesticides
439:Teratogen
414:0.08 mmHg
337:Molar mass
209:IP6ATU242I
136:ChemSpider
112:3D model (
91:CAS Number
67:IUPAC name
18:Cyclodiene
1109:epidermis
1094:congested
1052:edematous
1048:hyperemic
1033:systems.
1022:lethality
999:lethality
969:biomarker
965:porphyrin
929:Excretion
884:oxidation
882:Complete
830:butadiene
769:Reactions
737:isobenzan
722:acetylene
708:chlordane
1331:(NIOSH).
1258:such as
1256:polymers
1191:necrosis
1098:necrosis
1061:diarrhea
911:nonpolar
702:dieldrin
661:+ 2 HCl
638:+ 4 HCl
607:alkaline
419:Hazards
1325:"#0315"
1237:lindane
1215:History
1209:hepatic
1201:Cardiac
1195:bronchi
1193:in the
1179:lesions
1162:enzymes
1079:of the
1067:in the
1065:lesions
954:Effects
818:oxidize
794:alkenes
687:adducts
622:+ 6 Cl
528:what is
526: (
368:Density
176:PubChem
101:77-47-4
1621:; VSP;
1533:: 68.
1398:
1363:
1264:kepone
1135:X-rays
1018:lethal
1007:lipids
986:asthma
961:enzyme
822:ketone
718:endrin
694:aldrin
579:liquid
573:, and
523:verify
520:
342:272.76
292:SMILES
61:Names
1598:(PDF)
1288:Nylon
1252:Mirex
1248:dimer
1221:diene
1187:edema
1143:sinus
1139:nasal
943:feces
939:urine
907:polar
749:from
739:from
720:from
710:from
696:from
653:â C
626:â C
551:HCCPD
498:N.D.
472:none
456:NIOSH
257:InChI
114:JSmol
1619:1987
1433:1949
1416:link
1396:ISBN
1361:ISBN
1286:and
1203:and
1189:and
1075:and
1050:and
1029:and
812:and
781:(OR)
755:SOCl
670:and
575:dyes
492:IDLH
358:Odor
200:UNII
189:6478
145:6233
1535:doi
1388:doi
1353:doi
1131:ppm
597:of
479:REL
466:PEL
226:EPA
179:CID
1655::
1575:^
1555:.
1531:48
1529:.
1496:.
1440:^
1412:}}
1408:{{
1394:.
1359:.
1337:^
1327:.
1309:^
1185:,
1181:,
898:.
785:.
777:Cl
657:Cl
649:Cl
634:Cl
569:,
561:Cl
327:Cl
1641:.
1607:.
1559:.
1541:.
1537::
1500:.
1482:.
1418:)
1404:.
1390::
1369:.
1355::
783:2
779:4
775:5
757:2
659:6
655:5
651:8
647:2
645:H
643:5
641:C
636:8
632:2
630:H
628:5
624:2
620:6
618:H
616:5
614:C
563:6
559:5
549:(
518:Y
330:6
324:5
321:C
228:)
224:(
116:)
20:)
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