3194-55-6BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1BrDEIGXXQKDWULML-UHFFFAOYSA-N1,2,5,6,9,10-hexabromocyclododecane is a bromoalkane consisting of cyclododecane bearing six bromo substituents at positions 1, 2, 5, 6, 9 and 10. It has a role as a xenobiotic, a neurotoxin and a persistent organic pollutant. It is a brominated flame retardant, a bromohydrocarbon and a bromoalkane.
3194-55-6DTXSID4027527CHEMBL375298CHEBI:134063Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Warning
H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P260, P263, P264, P270, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.8% (3 of 367) of reports.
Warning
H315 (17.4%): Causes skin irritation [Warning Skin corrosion/irritation]
Chemical: Cyclododecane, 1,2,5,6,9,10-hexabromo-
Hazard Traits - Bioaccumulation; Endocrine Toxicity; Environmental Persistence; Neurotoxicity; Reproductive Toxicity
S - indicates a substance that is identified in a final Significant New Use Rule.
Substance: 1,2,5,6,9,10-hexabromocyclododecane
Substance: 1,2,5,6,9,10-hexabromocyclododecane
An estimated 100 to 999 workers are exposed to this chemical during manufacturing, processing, and use in the US. The product used in animal testing was hexabromocyclododecane (mixed isomers), also called Firemaster 100. There were no deaths after a 24-hour application to 20-30% of the body surface area, so the dermal LD50 (rabbit) was >20 gm/kg. The same chemical was used in the inhalation study, and the animals exhibited slight dyspnea, but no deaths, after 4-hour exposures to visibly dusty conditions. The LC50 (rats) was >202 mg/L/4h. Testing for eye irritation was negative. [HSDB] May cause irritation; [MSDSonline]
Law RJ et al.; Hexabromocyclododecane Challenges Scientists and Regulators. ENVIRONMENTAL SCIENCE & TECHNOLOGY 281A -287A (2005). This paper describes possible HBCD stereoisomers and related scientific and regulatory challenges.[Law RJ et al.; ENVIRONMENTAL SCIENCE & TECHNOLOGY 281A -287A (2005); Available from, as of March 6, 2015: http://www.novaquatis.eawag.ch/media/20050725/2507_artikel_science_techn.pdf]
1,2,5,6,9,10-hexabromocyclododecane (HBCD) is a brominated flame retardant consisting of a mixture of diastereomeric pairs of enantiomers that is a known omnipresent, environmental contaminant. The present study investigated the possibility of bioisomerization of HBCD stereoisomers. Therefore, mirror carps (Cyprinus carpio morpha noblis) were exposed to pure (+)- and (-)-gamma-HBCD, randomly sampled biweekly over a period of three and a half months and the fillets were subjected to enantiomer-specific determination of HBCD. Considering the background contamination of the fish at the beginning of the feeding period, significant enrichment of the respectively fed gamma-enantiomer was already detectable after two weeks of exposure. However, no significant enrichment of the respectively expected alpha-enantiomer was observed within this period. Thus, no evidence for the isomerization of HBCD stereoisomers was found in mirror carp under the applied conditions.
1,2,5,6,9,10-Hexabromocyclododecane (HBCD) is a high production volume cycloaliphatic used as an additive flame retardant primarily in polystyrene foam building materials. HBCD mixtures contain three major stereoisomers, alpha (a), beta (b), and gamma (g), at a typical ratio of 1.2:0.6:8.2. The toxicokinetic properties of the a and g isomers differ. For instance, a-HBCD has greater bioavailability and potential for accumulation in mice than g-HBCD. The present study reports comparative kinetics data for b-HBCD needed to support toxicological evaluations of HBCD mixtures. Results indicated that a single oral dose of 3mg/kg of [(14)C]-labeled b-HBCD was absorbed rapidly (> or = 85% total dose) in the female C57BL/6 mouse. The C max for b-HBCD-derived radioactivity in tissues, except adipose, was observed 3hr following gavage. Approximately 90% of the administered dose was excreted in urine and feces within 24hr, primarily as b-HBCD-derived metabolites. A portion of the dose (circa 9%) was excreted in feces as g-HBCD. Oral administration of 30 or 100mg/kg of b-HBCD resulted initially in slower rates of [(14)C] elimination; however, cumulative excretion data were similar across the dosing range 4 days postdosing. Residual concentrations of [(14)C] in tissues were highest in adipose and liver. b-HBCD-derived radioactivity accumulated in most tissues following four consecutive daily oral doses of 3mg/kg. The extent of metabolism and excretion of b-HBCD in female C57BL/6 mice was similar to that for g-HBCD. The potential for accumulation of b-HBCD-derived material in most tissues appeared to be less than for a-HBCD.
No reaction records under the current filter.
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European Commission, ESIS; Risk Assessment: Hexabromocyclododecane (25637-99-4) (May 2008).[Available from, as of March 3, 2009: http://esis.jrc.ec.europa.eu/]
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/11/90; Reporting date: 3/12/90.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexabromocyclododecane is included on this list. Effective date 1/11/90; Sunset date: 12/19/95.
Skin Irrit. 2 (17.4%)
Reproductive toxicity - category 2
Repr. 2
Wear self contained breathing apparatus for fire fighting if necessary.
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Avoid breathing dust. For personal protection see section Environmental precautions Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. 6.3 Methods and materials for containment and cleaning up Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging Dispose of as unused product.
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Skin protection: Handle with gloves.
Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Control of environmental exposure: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.
Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Thyroid hormone (TH) plays an essential role in growth and differentiation of the central nervous system. Deficiency of TH during perinatal period results in abnormal brain development known as cretinism in human. We recently reported that an environmental chemical 1,2,5,6,9,10-a-hexabromocyclododecane (HBCD) suppressed TH receptor (TR)-mediated transcription. To examine the effect of HBCD on cerebellar granule cells, we used purified rat cerebellar granule cells in reaggregate culture. Low dose HBCD (10(-10)M) significantly suppressed TH-induced neurite extension of granule cell aggregate. To clarify further the mechanisms of such suppression, we added brain-derived neurotrophic factor (BDNF) into culture medium, since BDNF plays a critical role in promoting granule cell development and is regulated by TH. BDNF completely rescued HBCD-induced suppression of granule cell neurite extension in the presence of T3. These results indicate that HBCD may disrupt TH-mediated brain development at least in part due to a disruption of the T3 stimulated increase in BDNF and BDNF may possess ability to ameliorate the effect of HBCD in granule cells.
EC50; Species: Lepomis macrochirus, Rafinesque (Bluegill sunfish); Conditions: static; Concentration: >100 mg/L for 96 hr (nominal concentration); Effect: no abnormal behavior was observed in any of the concentrations tested
EC50; Species: Daphnia magna (Water flea); Conditions: static, 20 °C; Concentration: 146 mg/L for 48 hr (95% confidence limit: 146.25-146.43 mg/L); Effect: mortlaity, immobility /Hexabromid S, purity about 92%)/
EC50; Species: Scenedesmus subspicatus (algae); Concentration: >500 mg/L for 96 hr; Effect: growth inhibition, biomass /Conditions of bioassay not specified in source examined/ /Hexabromid S/
IDENTIFICATION AND USE: HBCD technical grade consists of a mixture of isomers, predominantly the alpha-, beta, and gamma-enantiomeric pairs. The main use for HBCD is as an additive-type flame retardant for extruded and expanded polystyrene foam. Other applications include crystal and high-impact polystyrene, SAN (Styrene-AcryloNitrile) resins, adhesives, and coatings. HUMAN EXPOSURE AND TOXICITY: Human data not found. ANIMAL STUDIES: The chemical was not an eye irritant in rabbits, ant it minimally irritating to the skin of rabbits. In acute oral toxicity study in rats the following non-lethal toxicity signs were observed during the 14-day observation time. Females: diarrhea in 1 of 5, hypoactivity in 1 of 5. Males: hypoactivity in 3 of 5, corneal opacity in 3 of 5 and ptosis in 3 of 5. None of the animals died. In inhalation study 90 minutes after initiation of exposure to the end of the 4 hours exposure period the rats exhibited slight dyspnea. In developmental study in rats HBCD exerted a weak hypothyroidism evident with increases in thyroid weight, thyroid follicular cell hypertrophy and serum concentrations of thyroid-stimulating hormone as well as decreases of serum T(3) concentrations in offspring at 10,000 ppm at weaning. Increased thyroid weights and decreased serum T(3) concentrations were also observed in the adult stage from 1000 ppm. With regard to the effect on brain development, HBCD reduced density of CNPase-positive oligodendrocytes at 10,000 ppm, suggesting an impaired oligodendroglial development. Low-dose HBCD can potentially disrupt thyroid hormone-mediated transactivation and impairs Purkinje cell dendritogenesis, suggesting that HBCD can interfere with thyyroid hormone action in target organs, including the developing brain.
EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of December 8, 2014: http://actor.epa.gov/dashboard/]
/LABORATORY ANIMALS: Acute Exposure/ In an acute dermal toxicity study 2 male and 2 female New Zealand White rabbits were used. The hair was removed from the back (20-30% of the body surface). HBCDD (a white powder identified as "Firemaster 100") was applied once at a dosage level of 20 g/kg. The area of application was bandaged and occluded. The bandages were removed 24 hours later and the backs were washed. The animals were observed daily thereafter for a total of 14 days. None of the animals died. There is no information if any nonlethal signs of toxicity appeared. Minimal lethal dose by dermal route is thus greater than 20 g/kg. The study was not performed according to current guidelines. /Firemaster 100/
/LABORATORY ANIMALS: Acute Exposure/ In an acute oral toxicity study of HBCDD, 5 male and 5 female rats (Charles River CD strain) were used. The test material (a white powder identified as "Firemaster 100") was suspended in corn oil (particle size unknown) and administered orally by gavage at a dosage level of 10 g/kg in a volume of 20 mL/kg. The rats were observed for mortality and toxic signs during the first four hours after dosing, at 24 hours and then daily for 14 days. The following non-lethal toxicity signs were observed during the 14-day observation time. Females: diarrhea in 1 of 5, hypoactivity in 1 of 5. Males: hypoactivity in 3 of 5, corneal opacity in 3 of 5 and ptosis in 3 of 5. None of the animals died. Minimum lethal dose by oral dosing is then greater than 10 g/kg. The study was similar to the OECD guideline limit test. /Firemaster 100/
/LABORATORY ANIMALS: Acute Exposure/ Five Charles River CD rats of each sex were used in an acute inhalation toxicity study. The animals were whole body exposed to a dust of HBCDD (a white powder identified as "Firemaster 100", unknown particle size) at a concentration of 202 mg/L for 4 hours. The authors noted, "the chamber atmosphere was extremely dusty". The immediate (first 10 minutes) response to the dusty atmosphere was an increase of activity in preening. 90 minutes after initiation of exposure to the end of the 4 hours exposure period the rats exhibited slight dyspnea. During the 14 days observation period the animals appeared normal. No deaths occurred. The study was not performed according to current guidelines. /Firemaster 100/
/LABORATORY ANIMALS: Acute Exposure/ Three male and 3 female New Zealand White rabbits were used for an eye irritation study. The eyes of the rabbits (weight 2003 to 2220 g) were examined with ultraviolet light following instillation of a sodium fluorescein solution. The rabbits received 100 mg of HBCDD ("Firemaster 100") placed into the cupped conjunctival sac of the right eye, then the eyelids were gently held together for one second. The left eye served as the untreated control for each rabbit. The eyes were examined 24, 48, 72 hours and 7 days following instillation. The scores for iris and cornea were zero so the results refer to the effects on conjunctiva. The group average scores 0.6, 1.0, 1.0, and 0 respectively at the different time points. The total maximum score possible was 110. Based on the scores obtained it was concluded that the test material is not a primary eye irritant and according to EU criteria it does not classify as an eye irritant. /Firemaster 100/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Halogenated aliphatic hydrocarbons and related compounds/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with sterile dressings after decontamination ... . /Halogenated aliphatic hydrocarbons and related compounds/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of cardiac irritability and fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Halogenated aliphatic hydrocarbons and related compounds/
LD50 Rat oral > 10,000 mg/kg. /Firemaster 100/
LC50 Rat inhalation > 202 mg/L for 4 hours. /Firemaster 100/
LD50 Rabbit dermal > 20,000m g/kg. /Firemaster 100/
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/11/90; Reporting date: 3/12/90.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexabromocyclododecane is included on this list. Effective date 1/11/90; Sunset date: 12/19/95.
Used as a flame retardant in polystyrene foam and low-density polystyrene foam; Also used in high-impact polystyrene, styrene-acrylonitrile resins, adhesives, and coatings; [HSDB]
Working with Glues and Adhesives [Category: Other]
Brominated additive flame retardant. Use: EPS: Expanded polystyrene; HIPS: High-impacted polystyrene. /From table/
The main use for HBCD /1,2,5,6,9,10-hexabromocyclododecane/ is as an additive-type flame retardant for extruded and expanded polystyrene foam. Other applications include crystal and high-impact polystyrene, SAN (Styrene-AcryloNitrile) resins, adhesives, and coatings.
... Used in thermal insulation building materials, upholstery textiles, electronics.
Cyclododecane, 1,2,5,6,9,10-hexabromo- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5698]
... manufactured or imported in the US between 10 and 50 million pounds in 2005.
Cyclododecane, 1,2,5,6,9,10-hexabromo- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
For more U.S. Production (Complete) data for 1,2,5,6,9,10-HEXABROMOCYCLODODECANE (6 total), please visit the HSDB record page.
... Produced by the addition reaction of bromine to trans, trans, cis-1,5,9-cyclododecatriene, the cyclic trimer of butadiene. The hexabromocyclododecane that is obtained from this reaction consists of a mixture of stereoisomers of 1,2,5,6,9,10-hexabromocyclododecane ranging from oils to an isomer with a 205-208 °C melting point. Commercially available hexabromocyclododecane contains a mixture of solid isomers and has a melting point range of 170-180 °C (185-195 °C).
Cyclododecane, 1,2,5,6,9,10-hexabromo-: ACTIVE
Additive flame retardant used in low-density polystyrene foam...adequate to produce foam that meets building code requirements in the U.S.
Uses1. It can be used in smoldering, for polystyrene foamed plastics, polypropylene and polyester, acrylic, polypropylene and other fabrics as smoldering finishing agent. 2. It is mainly used for thermoplastic and thermosetting polymers which have fire retardant requirements. It is particularly suitable for extrusion of foaming polystyrene. 3. It is used for the fire-retardant polystyrene of polypropylene plastics and fibers. It can also be used for the fire retardancy of finishing and leather double-sided coat after the fire-retardancy of polyester fabric. When used as additive fire retardants, it is especially suitable for polystyrene, unsaturated polyester, polycarbonate, polypropylene, synthetic rubber or the like.
Uses1,2,5,6,9,10-Hexabromocyclododecane(HBCD) was used to compare the efficiency of different advanced extraction techniques for the recovery of brominated flame retardants from styrenic polymers. It was used to study the kinetics of the thermal and photolytic segregation of HBCD using HPLC.
General Description1,2,5,6,9,10-Hexabromocyclododecane(HBCD) is a brominated flame retardant. It is used in the textile industry and polystyrene foam manufacturing. Electrochemical reduction of HBCD at carbon and silver cathodes has been studied using cyclic voltammetry and controlled-potential electrolysis.
DefinitionChEBI: 1,2,5,6,9,10-hexabromocyclododecane is a bromoalkane consisting of cyclododecane bearing six bromo substituents at positions 1, 2, 5, 6, 9 and 10. It has a role as a neurotoxin, a persistent organic pollutant and a xenobiotic. It is a bromoalkane, a bromohydrocarbon and a brominated flame retardant.
For more Non-Human Toxicity Excerpts (Complete) data for 1,2,5,6,9,10-HEXABROMOCYCLODODECANE (7 total), please visit the HSDB record page.