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2,2',3,3',4,4',5,5',6,6'-デカブロモ-1,1'-ビフェニル

Decabromobiphenyl

HCID 26164
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
13654-09-6
標準SMILES
Brc1c(Br)c(Br)c(-c2c(Br)c(Br)c(Br)c(Br)c2Br)c(Br)c1Br
InChIKey
AQPHBYQUCKHJLT-UHFFFAOYSA-N
分子式
C12Br10
平均分子量
943.2 g/mol
単同位体質量
933.1834

概要

2,2',3,3',4,4',5,5',6,6'-Decabromobiphenyl is a polybrominated biphenyl. Polybrominated biphenyls (PBBs) are a group of 209 synthetic organic compounds with 1-10 bromine atoms attached to biphenyl. They can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)

名称と識別子

優先名称
Decabromobiphenyl
IUPAC
1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene
現地名
2,2',3,3',4,4',5,5',6,6'-デカブロモ-1,1'-ビフェニル
英語名
Decabromobiphenyl
分子式
C12Br10
分子量
943.17

名称と別名

DECABROMOBIPHENYL13654-09-6DecabromodiphenylPerbromobiphenylBerkflam B 10Flammex B 101,1'-Biphenyl, 2,2',3,3',4,4',5,5',6,6'-decabromo-PBB 209Adine 0102MID95LP5LVDeca-BB2,2',3,3',4,4',5,5',6,6'-Decabromobiphenyl
名称をさらに表示
デカブロモジフェニル2,2',3,3',4,4',5,5',6,6'-デカブロモ-1,1'-ビフェニル2,2',3,3',4,4',5,5',6,6'-デカブロモビフェニルデカブロモ-1,1'-ビフェニルデカブロモビフェニルデカブロモビフェニールペルブロモビフェニルデカブロモビフェニル標準品デカブロモビフェニル標準液CS_N-11568-10MG_デカブロモビフェニルデカブロモビフェニル (35ΜG/ML イソオクタン:アセトン(98:2))デカブロモビフェニル 100ΜG/ML IN HEXANEBB 209PBB-209adine0102flammexb10PBB NO 209berkflamb10PBB-No. 209 25
DTXSID9065572RefChem:131144DTXCID80343721,2,3,4,5-pentabromo-6-(pentabromophenyl)benzene237-137-21,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzeneDecabromobiphenyl (PBB 209)Decabromo-1,1'-biphenyl

データベース識別子

CAS
13654-09-6
PubChem CID
26164
DTXSID
DTXSID9065572
UNII
MID95LP5LV
EC Number
237-137-2
Nikkaji
J53.457I

物性

構造計算による物性

XLogP
10.5
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
22
形式電荷
0
複雑度
326

実験および物理化学的性質

PolymersOther Classes -> Halogenated Polyaromatics
LogP · 2 件

log Kow = 8.58

8.58

Color/FormWhite solid
SolubilityModerately soluble in chlorobenzene and o-xylene
Melting Point380-386 °C
Vapor Pressure3.98X10-10 mm Hg at 25 °C
Physical DescriptionWhite solid; [HSDB] White powder; [MSDSonline]
Collision Cross Section199.7 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

物理化学的性質

融点
378 · 378-379℃
沸点
568.3 · 568.3±45.0 °C(Predicted)
比重(密度)
2.979 · 2.979±0.06 g/cm3(Predicted)
溶解性
Chloroform (Slightly), THF (Slightly)
外見
Solid
色
Off-White to Pale Red
Henry's Law Constant
2.3 · 2.3×102 mol/(m3Pa) at 25℃, HSDB (2015)
EPAの化学物質情報
1 · 1,1'-Biphenyl, 2,2',3,3',4,4',5,5',6,6'-decabromo- (13654-09-6)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Danger

H350: May cause cancer [Danger Carcinogenicity]

危険有害性情報

Regulatory Information · 2 件

S - indicates a substance that is identified in a final Significant New Use Rule.

Restricted substance: Decabromo-1,1'-biphenyl

Other Safety InformationPEC / SN / Other assessments - Polybrominated flame retardants (PBFRs): Health and Environment
Hazards Summary · 1 件

Emergency medical treatment: see PCB-PBB; Some evidence of long term occupational exposure having adverse effects to thyroid, testicles, and epididymis; Effects to liver observed in 13 week feeding study with rats include vacuolization and distension of centrilobular hepatocytes; No evidence of embryotoxicity or teratogenicity; [HSDB] See Polybrominated biphenyls.

Hazard Classes and Categories · 3 件

Carc. 2 (100%)

Skin corrosion/irritation - Category 3

Carcinogenicity - Category 1B

安全と保護具

Disposal Methods · 1 件

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.

Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (L134)

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health EffectsPBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (L628)
Ecotoxicity ValuesEC50 Daphnia magna (immobilization) >66 mg/L/24 hr
Environmental Fate · 3 件

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.

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral (L628) ; inhalation (L628) ; dermal (L628)
Toxicity Summary · 1 件

The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)

Ecotoxicity Excerpts · 1 件

/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.

Animal Concentrations · 1 件

The concentration of decabromobiphenyl was <1 ug/kg wet weight from harbor seals collected from the North Sea(1). In whitebeaked dolphins from the North Sea, the concentration of decabromobiphenyl was <0.9 ug/kg wet weight(1). Decabromobiphenyl concentration was <0.5 ug/kg wet weight in sperm whales from the Atlantic Ocean(1).

Signs and SymptomsSymptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629)
Soil Adsorption/Mobility · 1 件

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).

Human Toxicity Excerpts · 3 件

/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/

安全データ

tsca
TSCA listed
ridadr
3152
化審法
一般化学物質
安衛法
57,57-2
消防法
危-4-1-II
hazard_class
9
packing_group
II
有毒物質データの
13654-09-6(Hazardous Substances Data)

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

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.

PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)

用途と製造

Uses · 4 件

Used in flame retardants; Commercial mixture contains 2.9% nonabromobiphenyl and 0.3% octabromobiphenyl; No longer commercially used or produced in the US; [HSDB]

Manufacture discontinued in the US in 1979; [HSDB]

Ingredient in flame retardants. /Former use/

PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)

U.S. ExportsApproximately 807,000 pounds of octa- and decabromobiphenyl was exported in 1976.
U.S. Production · 2 件

(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.

Formulations/Preparations · 2 件

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/

General Manufacturing Information · 2 件

1,1'-Biphenyl, 2,2',3,3',4,4',5,5',6,6'-decabromo-: INACTIVE

Production of decabromobiphenyl was discontinued in the United States in 1979.

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