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Chlorendic acid

Chlorendic acid structure

Chlorendic acid 

structure
  • CAS No:

    115-28-6

  • Formula:

    C9H4Cl6O4

  • Chemical Name:

    Chlorendic acid

  • Synonyms:

    Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid,1,4,5,6,7,7-hexachloro-;5-Norbornene-2,3-dicarboxylic acid,1,4,5,6,7,7-hexachloro-;1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid;Chlorendic acid;1,4,5,6,7,7-Hexachlorodicyclo-(2.2.1)-5-heptene-2,3-dicarboxylic acid;Hexachloroendomethylenetetrahydrophthalic acid;HET acid;1,4,5,6,7,7-Hexachlorobicyclo-(2,2,1)hept-5-en-2,3-dicarboxylic acid;2H,3H-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid;1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic acid;NSC 22231;NSC 41876;1,2,3,4,7,7-Hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid;5343-97-5;7374-78-9;888949-13-1

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Chlorendic acid is a colorless crystalline solid.ChEBI: A bridged organochlorine compound resulting from the Diels-Alder reaction of hexachlorocyclopentadiene with maleic anhydride followed by hydrolysis of the resulting anhydride. A chemical intermediate used in the preparation of fire-retardant polyester resi s and plasticisers.Fine white free-flowing crystals or white powder. Odorless.


Chlorendic acid appears as fine white free-flowing crystals or white powder. Odorless. (NTP, 1992)


Chlorendic acid appears as fine white free-flowing crystals or white powder. Odorless. (NTP, 1992)|Chlorendic acid is a bridged organochlorine compound resulting from the Diels-Alder reaction of hexachlorocyclopentadiene with maleic anhydride followed by hydrolysis of the resulting anhydride. A chemical intermediate used in the preparation of fire-retardant polyester resins and plasticisers. It has a role as a carcinogenic agent. It is an organochlorine compound, a dicarboxylic acid and a bridged compound.

Chlorendic acid Basic Attributes

388.827

388.84

204-078-9

41876|22231|519

DTXSID2020268

Crystalline solid

2917209090

Characteristics

74.6

2.30

Chlorendic acid appears as fine white free-flowing crystals or white powder. Odorless. (NTP, 1992)

0.95 (NTP, 1992)

209 °C

175°C (rough estimate)

239.1±28.7 °C

1.658

In water, 0.35 g/100 g @ 25 deg C

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

1.4X10-8 mm Hg @ 25 deg C /Estimated/

Henry's Law constant=3.0X10-14 atm-cu m/mole @ 25 °C /Estimated/

pKa=3.1

Loses water in a heated open system to give the anhydride; emits chlorine when heated to decomposition.|Hydroxyl radical rate constant=8.2X10-12 cu cm/molecule-sec @ 25 °C /Estimated/

Insoluble in water.

Acids, Carboxylic

CHLORENDIC ACID readily forms salts with a variety of metals (NTP, 1992).

Safety Information

UN2928 Toxic solids, corrosive, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material, Technical Name Required.

3

R40;R41

53-22-26-36/37/39-45

RB9000000

Xi

Stable. Incompatible with strong oxidizing agents.

P280-P305 + P351 + P338

H318-H351

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.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for CHLORENDIC ACID (6 total), please visit the HSDB record page.

The acid loses water in a heated open system, tends to discolor and forms the anhydride, which melts at 230-235 °C. ...Readily forms salts with a variety of metals, forms esters by heating with or without azeotropic solvent (e.g., chlorobenzene) and readily forms alkyl-type polyester resins by reaction with glycols and other polyols.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Chlorendic Acid in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 304 (1987) NIH Publication No. 87-2560|National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Chlorendic Acid (115-28-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s033chlo.pdf]|WHO; Environ Health Criteria 185: Chlorendic acid and anhydride (1996). Available from: http://www.inchem.org/documents/ehc/ehc/ehc185.htm as of July 7, 2004.

This chemical will burn when subject to direct flame, but is self-extinguishing when the flame is removed. (NTP, 1992)

|Danger|H315 (75.1%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 257 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for CHLORENDIC ACID (10 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Three of three leachate samples collected in 1990 from a Swedish municipal landfill receiving mainly domestic waste contained chlorendic acid at unreported concentrations(1).

Toxicity

After oral and intravenous administration of radiolabelled chlorendic acid to rats, the substance was rapidly distributed throughout the body and rapidly metabolized. More than 90% of the radiolabel was excreted within 24 hr in the feces, mainly in a conjugated form. Only 3-6% was excreted in the urine. The highest concentrations of radiolabel were found in adipose tisue, liver, kidneys, whole blood and lung. ... The acute oral toxicity /for the rat/ is low ... Chlorendic acid and anhydride are skin irritants and severe eye and respiratory tract irritants in the rabbit. ... Chlorendic acid was tested for mutagenic potential ... in Salmonella typhimurium in the presence and absence of an exogenous metabolism system. Negative results were obtained ... A mouse lymphoma mutation assay in the absence of an exogenous metabolism system was positive. ... Chlorendic acid was positive in a transformation assay using BALB/c3T3 cells without metabolic activation ... Chlorendic acid did not give an increase of replicative DNA synthesis after oral or subcutaneous application ... to rats. ... Chlorendic acid was tested for carcinogenic potential in ... rats ... In addition to significant non-neoplastic changes in a number of organs, such as cystic degeneration and focal cellular changes, and bile duct hyperplasia in the liver, increases in the incidence of hepatocellular adenomas ... and carcinomas, significant at the highest dose level, ... were found. Furthermore, slight increases in acinar cell adenomas of the pancreas and alveolar/bronchiolar adenomas in the lung were found ... Chlorendic acid tested in ... mice ... showed an increased incidence of necrosis and mitotic alteration in the liver. An increase in the incidence of hepatocellular adenomas and carcinomas was found ... An increased incidence of alveolar/bronchiolar adenomas or carcinomas was found ... Tests showed that chlorendic acid has promoting activity. ... Data on the exposure of humans and of organisms in the environment are lacking. Both substances /chlorendic acid and its anhydride/ seem to have low acute and subacute oral toxicity, but they are dermal, eye, and respiratory irritants. From the results of long term toxicity/carcinogenicity studies with chlorendic acid on rats and mice, it is concluded that chlorendic acid induces tumors in rats and mice and is, therefore, considered to have a carcinogenic potential. However, a full hazard assessment for humans and the environment cannot be made in view of the lack of data.

LD50 Rat oral 1770 mg/kg bw

/AQUATIC SPECIES/ In short term flask studies, 500 mg/L (ph 3.5) completely inhibited algal growth and microfaunal activity; 250 mg/L (ph 4.1) inhibited microfaunal activity and reduced abundance of all but 1 algal species; and 125 mg/L (ph 6.6) had no effects. In longer term microcosm studies 500 and 250 mg/L decreased oxygen production and respiration, and altered chlorophyll concentration and bacterial populations.|/OTHER TERRESTRIAL SPECIES/ ...The effect of chlorendic acid on soil microorganisms /was studied/. A silty clay soil was treated with 0, 1 or 10 mg/kg chlorendic acid in Erlenmeyer flasks and incubated at 30 °C for 28 days. A significant increase in the number of soil fungi was reported for the 10-mg/kg group, but no effects on soil fungi were reported at 1 mg/kg. A non-significant increase in the number of bacteria was reported for both treated soils.

Toxicology and carcinogenesis studies of chlorendic acid (greater than 98% pure) were conducted by administering the chemical in feed to groups of 50 male and 50 female F344/N rats for 103 weeks. The estimated mean daily consumption of chlorendic acid was 27 and 56 mg/kg body weight for low dose male rats and 39 and 66 mg/kg for low dose and high dose female rats. Survival and feed consumption of dosed male and female rats ... were similar to those of controls. Mean body weights of high dose male and female rats ... were lower than those of controls. Mean body weights of high dose female rats 16%-24% lower than those of controls during the second half of the study. Incidences of nonneoplastic lesion of the liver in dosed male rats (cystic degeneration) and dosed female rats (granulomatous inflammation, pigmentation, and bile duct hyperplasia) were increased. The incidences of neoplastic nodules of the liver were significantly increased in dosed male rats (control, 2/50; low dose, 21/50; high dose, 23/50) and high dose female rats (1/50; 3/49; 11/50). The incidence of hepatocellular carcinomas was also increased in high dose female rats (0/50; 3/49; 5/50). The incidences of acinar cell hyperplasia (0/49; 4/50; 4/50) and acinar cell adenomas (0/49; 4/50; 6/50) of the pancreas were increased in dose male rats relative to those of contols. Pancreatic acinar cell adenoma is an uncommon neoplasm in intreated control F344/N rats in NTP studies (3/1667). In dosed male rats, incidences of alveolar/bronchiolar adenomas of a the lung (0/50; 3/50; 5/50) were increased. The incidences of alveolar/bronchiolar adenomas of carcinomas (combined) in dosed female mice were also increased (1/50;5/50; 6/50). Preputial gland carcinomas occurred at a greater incidence in low dose male rats (1/50;8/50; 4/50) than in controls. An adenoma and a squamous cell papilloma were observed in two low dose male rats. The incidences of sarcomas, fibrosarcomas, or neurofibrosarcomas (combined) of the salivary gland (1/50;2/49;4/50) were increased in dosed male rats. The incidences in the dosed groups were not significantly different from that in the controls, but these tumors are uncommon in F344/N rats receiving no treatment (3/1689). There was clear evidence of carcinogenicity of chlorendic acid for male F344/N rats as shown by increased incidences of neoplastic nodules of the liver and acinar cell adenomas of the pancreas. Increased incidences of alveolar/bronchiolar adenomas and preputial gland carcinomas may also have been related to the administration of chlorendic acid. There was clear evidence of carcinogenicity of chlorendic acid for female F344/N rats as shown by increased incidences of neoplastic nodules and of carcinomas of the liver.|Toxicology and carcinogenesis studies of chlorendic acid (greater than 98% pure) were conducted by administering the chemical in feed to groups of 50 female ... B6C3F1 mice at concentrations of 0, 620, or 1,250 ppm for 103 weeks. ... The estimated daily consumption was 89 and 185 mg/kg for low dose and high dose males and 100 and 207 mg/kg for low dose and high dose females. ... Survival and feed consumption of dosed male and female ... mice ... were similar to those of controls. Mean body weights of high dose male and female rats and mice were lower than those of controls. Mean body weights of high dose female rats were 16%-24% lower than those of controls during the second half of the study. ... The incidences of nonneoplastic lesions of the liver were increased in dosed males (coagulative necrosis) and high dose females (mitotic alterations). The incidences of hepatocellular adenomas (5/50; 9/49; 10/50), hepatocellular carcinomas (9/50; 17/49;20/50), and hepatocellular adenomas or carcinomas (combined) (13/50;23/49; 27/50) were increased in dosed male mice. Hepatocellular carcinomas metastasized to the lung in 2/50 control, 4/49 low dose, nad 7/50 high dose male mice. Hepatocellular adenomas or carcinomas (combined) were not significantly increased in female mice (3/50;7/49;7/50). ... There was clear evidence of carcinogenicity of chlorendic acid for male B6C3F1 mice as shown by increased incidences of hepatocellular adenomas and of hepatocellular carcinomas. There was no evidence of carcinogenicity of chlorendic acid for female B6C3F1 mice given chlorendic acid in the diet at concentrations of 620 or 1250 ppm for 103 weeks.

Chlorendic acid's production and use as a chemical intermediate in the manufacture of unsaturated polyester resins, in fiberglass reinforced resins for process equipment in chemical industries, to impart flame resistance to polyurethane foams, in the manufacture of alkyd resins for special paints and inks, and in flame-retardant treatment of wool fabrics(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a water solubility of 3500 mg/L(2) and a regression-derived equation(3), indicates that chlorendic acid is expected to have very high mobility in soil(SRC). The pKa of chlorendic acid is 3.1(7), indicating that this compound will primarily exist in anion form and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(8). Volatilization of chlorendic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Chlorendic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-8 mm Hg(SRC), determined from a fragment constant method(5). Based on data from several screening studies (2,6), chlorendic acid is not expected to biodegrade rapidly in the environment(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a water solubility of 3500 mg/L(2) and a regression-derived equation(3), indicates that chlorendic acid is not expected to adsorb to suspended solids and sediment(SRC). The pKa of chlorendic acid is 3.1(7), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to suspended solids and sediment than their neutral counterparts(5). Because chlorendic acid will exist almost entirely as the anion form at pH values of 5 to 9, volatilization from water surfaces is not expected to be an important fate process. In addition, based upon an estimated Henry's Law constant of 3.0X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4), volatilization from water surfaces is not expected(3). According to a classification scheme(6), BCF values of <2.1 and <0.22, measured in orange-red killifish(2), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Based on data from several screening studies(2,8), chlorendic acid is not expected to biodegrade rapidly in the environment(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorendic acid, which has an estimated vapor pressure of 1.4X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase chlorendic acid may be removed from the air by wet and dry deposition(SRC).

Chlorendic acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1). Chlorendic acid has a dissociation constant of 3.1 (2) indicating that this compound will exist primarily as a anion in the environment.|Would be expected to degrade by direct photolysis or by reaction with hydroxyl radicals and ozone.

2.09|BCF values of <0.22 and <2.1 were measured for chlorendic acid using orange-red killifish (Oryzias latipes) which were exposed over a 6-week period to chlorendic acid at 10 and 1 ug/L, respectively(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not altered physically or chemically once released into the environment.|Should have low potential for bioconcentration in organisms and food chains.

616.60 L/kg|The Koc of chlorendic acid is estimated as 49(SRC), using a water solubility of 3500 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chlorendic acid is expected to have very high mobility in soil. The pKa of chlorendic acid is 3.1(4), indicating that this compound will primarily exist in anion form and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5).

A pKa of 3.1(4) indicates chlorendic acid will exist almost entirely as the anion form at pH values of 5 to 9 and therefore volatilization from water and soil surfaces is not expected to be an important fate process(SRC). The Henry's Law constant for chlorendic acid is estimated as 3.0X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chlorendic acid is expected to be essentially nonvolatile from water surfaces(2). Chlorendic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Chlorendic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-8 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 55 workers (29 of these are female) are potentially exposed to chlorendic acid in the US(1). Occupational exposure to chlorendic acid may occur through dermal contact with this compound at workplaces where chlorendic acid is produced or used(SRC). The general population may be exposed to chlorendic acid via dermal contact with consumer products containing chlorendic acid(SRC).

Drug Information

(14)C Chlorendic acid was absorbed after oral dose of 7.7 umol/kg bw to Fischer 344 rats. Distribution in various tissues was similar from oral and iv routes. Liver was major site of deposition (primarily as metabolites) with smaller amount found in blood, muscle, skin and kidneys. It was excreted primarily through bile and feces. Urine contained <6% of total dose. Within 1 day, more than 75% of dose was excreted in feces, primarily as metabolites.|(14)C Chlorendic acid in a solution of a polyoxyethylated vegetable oil, ethanol and water (3 mg/kg body weight) was given to male Fischer 344 rats by intravenous injection or oral intubation. Following intravenous injection, more than 50% of the administered radioactivity was found in the liver within 15 min. Biliary excretion was the primary route of removal of radioactivity from the liver, which occurred with a half-life of 1.19 hr. The blood contained 20% of the administered radioactivity at 1 hr, and this declined with a half-life of 0.84 hr. Muscle contained 14% of the administered radioactivity at 15 min, and this level fell rapidly, with a half-life of 0.57 hr. Smaller amounts were detected in other organs. The highest specific activity per gram of tissue (wet weight) was noted in the adrenal gland early after administration. Administration of the same solution of (14)C chlorendic acid by oral intubation resulted in a somewhat higher liver concentration and a lower blood concentration at 24 hr than those seen after the same time following intravenous administration. The majority of the radioactivity was found in the feces (78% of the total dose) or large intestine.

Liver extracts of the animals exposed to 3 and 56 mg/kg showed unchanged chlorendic acid and at least one unidentified metabolite.|The (14)C chlorendic acid-derived radioactivity in the bile, urine and feces was attached mainly to parent compound or conjugates resistant to beta-glucuronidase and aryl sulfatase.

After iv administration of 14C-chlorendic acid (99%) in a solution of "Emulphor", ethanol and water, at 3 mg/kg body weight to male F-344 rats, ...the half-life of chlorendic-acid-derived radioactivity from liver into bile was 1.19 hr. The half-life for blood was 0.84 hr, for muscle tissue 0.57 hr and for skin 0.6 hr.

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes and mucous membranes. Inhalation may cause sneezing and coughing. Ingestion of this compound may cause nausea and a choking sensation. ACUTE/CHRONIC HAZARDS: This compound is an irritant of the skin, eyes and mucous membranes. When heated to decomposition it emits toxic fumes of chlorine. (NTP, 1992)|Carcinogens

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

chlorendic acid

Chlorendic acid Use and Manufacturing

Methods of Manufacturing

Chlorendic acid is synthesized by a Diels-Alder reaction of maleic anhydride and hexachlorocyclopentadiene in toluene followed by hydrolysis of the anhydride using aqueous base.

Uses

Chlorendic acid is used as a flame retardant in polyurethane foams, resins, plasticizers, coatings, epoxy resins, and wool fabrics; in the manufacture of alkyl resins for special paints and inks; in the manufacture of polyester resins with special applications in electrical systems,paneling, engineering plastics, and paint; and in the manufacture of corrosion-resistant tanks, piping, and scrubbers. Chlorendic acid is also used as an extreme-pressure lubricant (NTP 1987, IARC 1990, IPCS 1996, HS

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Commercial grade 99.5% ...Common impurities are as follows: unreacted maleic anhydride,

Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, 1,4,5,6,7,7-hexachloro-: ACTIVE

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:388.8
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:387.821125
Monoisotopic Mass:385.824075
Topological Polar Surface Area:74.6
Heavy Atom Count:19
Complexity:487
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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