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Decabromobiphenyl

Decabromobiphenyl structure

Decabromobiphenyl 

structure
  • CAS No:

    13654-09-6

  • Formula:

    C12Br10

  • Chemical Name:

    Decabromobiphenyl

  • Synonyms:

    1,1′-Biphenyl,2,2′,3,3′,4,4′,5,5′,6,6′-decabromo-;Biphenyl,decabromo-;2,2′,3,3′,4,4′,5,5′,6,6′-Decabromo-1,1′-biphenyl;Perbromobiphenyl;Flammex B 10;Berkflam B 10;Decabromobiphenyl;Adine 0102;2,2′,3,3′,4,4′,5,5′,6,6′-Decabromobiphenyl;PBB 209;RBF 102;BB 209;39282-95-6

  • Categories:

    Specialty Chemicals

Decabromobiphenyl Basic Attributes

943.2 g/mol

943.17

237-137-2

MID95LP5LV

DTXSID9065572

White solid

Characteristics

0 Ų

log Kow = 8.58

375 °C

Moderately soluble in chlorobenzene and o-xylene|In water, 1.24X10-11 mg/L at 25 °C (est)

3.97e-10 mmHg|3.98X10-10 mm Hg at 25 °C

Henry's Law constant = 4.2X10-8 atm-cu m/mole at 25 °C (est)

Safety Information

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.

|Warning|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P332+P313, P337+P313, P405, and P501

Decabromobiphenyl was detected in New Jersey soil and sludge samples at 2,100 and 390,000 ppb, respectively(1).

Toxicity

LD50 Rat oral >5 g/kg|LD50 Rat dermal >5 g/kg|LD50 Rabbit dermal >8 g/kg bw /from table/

/AQUATIC SPECIES/ In a short-term test (according to the ISO standard 6341) the immobilization of Daphnia magna (Crustacea) by technical decabromobiphenyl (Adine 0102) has been investigated. The following results were obtained after dissolution of the test material in DMSO because of its weak solubility in water. The maximum concentration resulting in 0% immobilization (24 hr): <2 mg/liter.

Decabromobiphenyl's former production and use as an additive in flame retardant materials(1), may have resulted in its release to the environment through various waste streams(SRC). Most decabromobiphenyl produced in the US was exported and US production was discontinued in 1979(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 994,000(SRC), determined from a structure estimation method(2), indicates that decabromobiphenyl will be immobile in soil(SRC). Volatilization of decabromobiphenyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant 4.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Decabromobiphenyl is not expected to volatilize from dry soil surfaces(SRC) based on its vapor pressure of 3.98X10-10 mm Hg(4). A screening study using an activated sludge inoculum indicated that decabromobiphenyl is not biodegradable(5). Biodegradation data on polybrominated biphenyls such as decabromobiphenyl indicate these compounds are persistent in the environment, but may slowly be degraded under anaerobic conditions(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 994,000(SRC), determined from a structure estimation method(2), indicates that decabromobiphenyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). According to a classification scheme(5), BCF values in the range of 0.6-5.4 measured in fish(6) suggests bioconcentration in aquatic organisms is low (SRC). Decabromobiphenyl is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(7). Brominated biphenyls have been shown to undergo direct photolysis in solutions(7), suggesting that there is potential for direct photolysis in sunlit surface waters(SRC). A screening study using an activated sludge inoculum indicated that decabromobiphenyl is not biodegradable under aerobic conditions(6). Biodegradation data on polybrominated biphenyls such as decabromobiphenyl indicate these compounds are persistent in the environment, but may slowly be degraded under anaerobic conditions(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), decabromobiphenyl, which has a vapor pressure of 3.98X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase decabromobiphenyl may be removed from the air by wet and dry deposition(SRC). Brominated biphenyls have been shown to undergo direct photolysis in solutions(3); however, it is unclear whether direct photolysis will occur for particulate phase decabromobiphenyl in the atmosphere.

Decabromobiphenyl is subject to direct photolysis in the environment with the subsequent formation of lower brominated biphenyls as degradation products(1). In the atmosphere, decabromobiphenyl will exist primarily in the particulate-phase, thus reaction with photochemically produced hydroxyl radicals is expected to be a slow abiotic degradation process(1). Decabromobiphenyl is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1).

1.55e+05|A BCF range of 0.6-5.4 was measured for carp exposed to 0.15 mg/L of decabromobiphenyl over a 6 week incubation period and a BCF of <4 was measured for carp exposed to 0.015 mg/L over a 6 week incubation period(1) According to a classification scheme(2), these BCF values suggests bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for decabromobiphenyl can be estimated to be 994,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that decabromobiphenyl is expected to be immobile in soil(SRC).

The Henry's Law constant for decabromobiphenyl is estimated as 4.2X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that decabromobiphenyl is expected to be essentially non-volatile from water and moist soil surfaces (3). Decabromobiphenyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.98X10-10 mm Hg(3).

Decabromobiphenyl is no longer produced or used in the United States(1,2); therefore, the potential for occupational exposure and exposure to the general public is considered low(SRC).

Drug Information

Analyses of fish captured from natural waters may also indicate the possibility of the debromination reaction in fish, unless selective accumulation or elimination takes place. In fish from water mainly contaminated with decabromobiphenyl, only the nona- and hexa bromobiphenyl congeners were present.

/EPIDEMIOLOGY STUDIES/ ...Thyroid dysfunction in workers exposed for at least 240 hr to decabromobiphenyl and decabromobiphenyl oxide over a 4-year period. The average period of employment was 3.9 years, mean age, 34.7 years. Medical questionnaires, physical examinations, and laboratory tests were conducted. For exposure data see section 5.3. Thyroid nodules were seen in 3 out of 18 workers exposed for 3 years or longer. ...Reproductive effects /were also studied/ in the same PBB workers. A significant correlation was seen between length of employment and concentrations of follicle stimulating hormone (FSH). An abnormal FSH value was found in only one worker. A testicular cyst was found in one exposed worker, and epididymal nodules in two others. No testicular or epididymal nodules were seen among controls. No definite statement could be made concerning adverse effects on the prevalence of testicular and epididymal nodules, because of their prevalence in the general population. /Commercial mixture/|/EPIDEMIOLOGY STUDIES/ Thyroid function was investigated in a cohort of 35 male workers, selected from 86 identified workers exposed for at least 6 weeks, manufacturing decabromobiphenyl, decabromobiphenyl ether, and bromine. The study revealed four cases of primary hypothyroidism (11.4%), but none in 89 control subjects. The bromine compounds were the only common exposure. A significantly higher number of the exposed workers had detectable serum levels of DeBB (0.5-1340 ng/mL)... . /Commercial mixture/|/BIOMONITORING/ Effects in workers exposed to unspecified PBBs and/or decabromobiphenyl included increased serum thyrotropin, low or borderline low serum T4, and increased thyroid antimicrosomal antibody titers. A spectrum of thyroid effects has been observed in exposed rats, ranging from decreases in serum levels of serum T4 and T3 to histological and ultrastructural changes. Therefore, serum levels of T4 and/or other thyroid hormones are potential biomarkers of effects for PBBs. /Commercial mixture/

BB-209

Decabromobiphenyl Use and Manufacturing

Uses

Ingredient in flame retardants. /Former use/

Production

(1990) 10 thousand - 500 thousand pounds|Approximately 807,000 pounds of octa- and decabromobiphenyl was produced in the US in 1976. Estimated production in 1975 was 170,000 pounds.

Commercial decabromobiphenyl (Flammex B 10) contained 96.8% decabromobiphenyl, 2.9% nonabromobiphenyl, and 0.3% octabromobiphenyl|Registered trade names: ...Adine 0102; Berkflam B 10 /from table/

1,1'-Biphenyl, 2,2',3,3',4,4',5,5',6,6'-decabromo-: INACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|Production of decabromobiphenyl was discontinued in the United States in 1979.

Computed Properties

Molecular Weight:943.2
XLogP3:10.5
Rotatable Bond Count:1
Exact Mass:943.17313
Monoisotopic Mass:933.1834
Heavy Atom Count:22
Complexity:326
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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