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Home > Encyclopedia > 1,2,5,6,9,10-Hexabromocyclododecane

1,2,5,6,9,10-Hexabromocyclododecane

1,2,5,6,9,10-Hexabromocyclododecane structure

1,2,5,6,9,10-Hexabromocyclododecane 

structure
  • CAS No:

    3194-55-6

  • Formula:

    C12H18Br6

  • Chemical Name:

    1,2,5,6,9,10-Hexabromocyclododecane

  • Synonyms:

    Cyclododecane,1,2,5,6,9,10-hexabromo-;1,2,5,6,9,10-Hexabromocyclododecane;Bromkal 73-6D;YM 88A;FR 1206HT;FR 1206;Pyroguard SR 104;SR 104;23774-70-1

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

It is white crystals and have two isomers with the melting point of low melting point type being 167-168 ℃ and high melting point type is 195-196 ℃. It has a good stability upon heat and ultraviolet light.
The above information is edited by the chemicalbook of Dai Xiongfeng. off-white to beige crystalline powder and chunks


DryPowder; PelletsLargeCrystals


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.

1,2,5,6,9,10-Hexabromocyclododecane Basic Attributes

641.7

641.70

221-695-9

66OON1WWOS

DTXSID4027527

2903890090

Characteristics

0

6.63

DryPowder; PelletsLargeCrystals

2.1±0.1 g/cm3

185-195 °C

505.2±50.0 °C at 760 mmHg

249.5±24.8 °C

1.598

acetone: soluble 25mg/mL, clear, colorless to light yellow

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

4.70e-07 mmHg

Safety Information

3077

1

36/37/38-64-50/53-63

22-24/25-61-60-36/37-53

GU2302500

Xi,N,Xn

Stable under recommended storage conditions.

P201-P260-P263-P273-P308 + P313-P391

H361-H362-H410

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.

Strong oxidizing agents

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]|European Commission, ESIS; Risk Assessment: Hexabromocyclododecane (25637-99-4) (May 2008).[Available from, as of March 3, 2009: http://esis.jrc.ec.europa.eu/]

|Warning|H315 (18.02%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P263, P264, P270, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 347 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P260, P263, P264, P270, P273, P281, P308+P313, P391, P405, and P501|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501

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.

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.

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.

Toxicity

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.

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.

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/

Drug Information

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.

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.

/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/

1,2,5,6,9,10-hexabromocyclododecane

1,2,5,6,9,10-Hexabromocyclododecane Use and Manufacturing

Methods of Manufacturing

First synthesize trans, trans, and cis-cyclododecane-1, 5, 9-triene (see also 10850): Add butyl titanate and diethyl aluminum chloride to benzene, and add it at a temperature below 55°C Butadiene, through the three polymerization reaction to generate trans, trans, cis-cyclododeca-1, 5, 9 triene (C12H18, [2765-79-9]). Then bromination gives hexabromocyclododecane. In a 2000L glass-lined reactor equipped with a reflux cooler and exhaust gas management device, 1300L ethanol, 278kg trans, cis-cyclodidi-1, 5, 9-triene and 872kg bromine were added. The feeding temperature is 15-25°C. During the entire feeding process, the presence of bromine was maintained, and the reactant was red. After the reaction, the hexabromocyclododecane generated by the excess odor needle was filtered and refined to obtain 1000kg of product with a yield of 91%. Another method is to use aluminum trichloride as a catalyst. In 800 parts of cyclododecane-1, 5, 9-triene and 1500 parts of ethanol, add 150 parts of aluminum trichloride at 15-25℃, and then add 2400 parts of bromine within 2h at 25-30℃, at room temperature The reaction was stirred for 5h, and then filtered. The filter cake was washed with 200 parts of ethanol and 2% sodium bicarbonate to obtain a yield of 86% of hexabromocyclododecane. If halogenated hydrocarbons are added to the ethanol solvent, the formation of resinous substances can be suppressed.

Uses

Used for flame retardant of polypropylene plastic and fiber, polystyrene foam plastic, flame retardant finishing of polyester fabric and flame retardant of vinylon coated double-sided leather. It can be used as an additive type combustion agent, suitable for polystyrene, unsaturated polyester, polycarbonate, polypropylene, synthetic rubber, etc.


Flame retardants


Building/construction materials not covered elsewhere

Production

1,000,000 - 10,000,000 lb|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#5703]|... manufactured or imported in the US between 10 and 50 million pounds in 2005.|For more U.S. Production (Complete) data for 1,2,5,6,9,10-HEXABROMOCYCLODODECANE (6 total), please visit the HSDB record page.

Technical grade consists of a mixture of isomers, predominantly the alpha-, beta, and gamma-enantiomeric pairs.

All other basic inorganic chemical manufacturing|Cyclododecane, 1,2,5,6,9,10-hexabromo-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|Additive flame retardant used in low-density polystyrene foam...adequate to produce foam that meets building code requirements in the U.S.

Computed Properties

Molecular Weight:641.7
XLogP3:7.1
Exact Mass:641.64473
Monoisotopic Mass:635.65088
Heavy Atom Count:18
Complexity:175
Undefined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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