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TETRABROMOBISPHENOL A

CAS-NO:79-94-7

SYNONYMS: Tetrabromobisphenol A; TETRABROMOBISPHENOL-A (ABS); Tetrabromodian;Tetrabromodiphenylolpropane 4,4′-Isopropylidenebis(2,6-dibromophenol); TBBPA; Tetrabromobisphenol; TETRABROMOBISPHENOL; 2,2-Bis (4'-hydroxy-3',-5'-dibromophenyl) propane; 2,2',6,6'-Tetrabrom; 4,4'-isopropylidendiphenol; 2,2',6,6'-tetrabromo; 4,4'-isopropilidendifenol; 2,2',6,6'-tetrabromo; 4,4'-isopropylidenediphenol; 2,2',6,6'-Tetrabromo; 4,4'-isopropylidenediphenol; 2,2',6,6'-Tetrabromobisphenol A; 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane; 2,2-Bis(4-hydroxy-3,5-dibromophenyl)propane; 3,3',5,5'-Tetrabromobisphenol A; 3,5,3',5'-Tetrabromobisphenol A; 4,4'-(1-Methylethylidene)bis[2,6-dibromophenol]; 4,4'-(1-Methylethylidene)bis[2,6-dibromophenol]; 4,4'-Isopropylidenebis[2,6-dibromophenol]; BIS(PHENOL, 2,6-DIBROMO), 4,4'-(1-METHYLETHYLIDENE); BISPHENOL A, TETRABROMO; BISPHENOL, 4,4'-(1-METHYLETHYLIDENE)TETRABROMO; Bromdian; CP 2000; FG 2000; Fire Guard 2000; Firemaster BP 4A; Flame Cut 120G; Flame Cut 120R; FR 1524; GLCBA 59P; NSC 59775; Phenol, 4,4'-(1-methylethylidene)bis[2,6-dibromo]; Phenol, 4,4'-(1-methylethylidene)bis[2,6-dibromo]; Phenol, 4,4'-isopropylidenebis[2,6-dibromo]; RB 100; Saytex CP 2000; Saytex RB 10;Saytex RB 100PC; tetrabromobisphenol A; TETRABROMOBISPHENOL-A (ABS); Tetrabromodian;Tetrabromodiphenylolpropane 4,4′-Isopropylidenebis(2,6-dibromophenol); TBBPA; Tetrabromobisphenol; TETRABROMOBISPHENOL; 2,2-Bis (4'-hydroxy-3',-5'-dibromophenyl) propane; 2,2',6,6'-Tetrabrom; 4,4'-isopropylidendiphenol; 2,2',6,6'-tetrabromo; 4,4'-isopropilidendifenol; 2,2',6,6'-tetrabromo; 4,4'-isopropylidenediphenol; 2,2',6,6'-Tetrabromo; 4,4'-isopropylidenediphenol; 2,2',6,6'-Tetrabromobisphenol A; 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane; 2,2-Bis(4-hydroxy-3,5-dibromophenyl)propane; 3,3',5,5'-Tetrabromobisphenol A; 3,5,3',5'-Tetrabromobisphenol A; 4,4'-(1-Methylethylidene)bis[2,6-dibromophenol]; 4,4'-(1-Methylethylidene)bis[2,6-dibromophenol]; 4,4'-Isopropylidenebis[2,6-dibromophenol]; BIS(PHENOL, 2,6-DIBROMO), 4,4'-(1-METHYLETHYLIDENE); BISPHENOL A, TETRABROMO; BISPHENOL, 4,4'-(1-METHYLETHYLIDENE)TETRABROMO; Bromdian; CP 2000; FG 2000; Fire Guard 2000; Firemaster BP 4A; Flame Cut 120G; Flame Cut 120R; FR 1524; GLCBA 59P; NSC 59775; Phenol, 4,4'-(1-methylethylidene)bis[2,6-dibromo]; Phenol, 4,4'-(1methylethylidene)bis[2,6-dibromo]; Phenol, 4,4'-isopropylidenebis[2,6-dibromo]; RB 100; Saytex CP 2000; Saytex RB 10;Saytex RB 100PC


Both hydroxyl groups on TBBPA can be reacted with epichlorohydrin under basic conditions to form the diglycidyl ether, which is widely used in epoxy resin formulations. 

TBBPA is also used in polycarbonate and ether polyester resins and is used as a chemical intermediate for the synthesis of tetra-bromobisphenol A allyl ether, -bis(2-hydroxyethyl ether), -carbonate oligomer, and -diglycidyl ether. 

TBBPA is also used as a flame retardant in plastics, paper, and textiles, and as a plasticizer in adhesives and coatings.

Being covalently bound to the polymer limits exposure to unbound excess chemical used in the manufacturing process.

The widespread use of TBBPA, and its environmental persistence in dust, sediments, and accumulation in biota, has led to increased concerns regarding its effects on wildlife and humans . 

Two different microbial transformations of TBBPA have been observed: reductive debromination to bisphenol A (BPA; 4,4′-isopropylidenediphenol) or O-methylation to TBBPA monomethyl ether and TBBPA dimethyl ether (TBBPA DME; 4,4′-isopropylidenebis(2,6-dibromo-1-methoxybenzene)) 

Sequential reductive dehalogenation of TBBPA to BPA under methanogenic and sulfate-reducing conditions has been demonstrated in anaerobic sediment cultures, and some community structure analysis under different conditions suggest that the microorganisms responsible for this degradation are bacteria; however, the specific organism responsible for the debromination is not known. 

Reductive dehalogenation of TBBPA has also been shown in sewage sludge in areas receiving leachate from contaminated landfills . 

Further anaerobic degradation of the BPA product has not been observed .

The transformation of halogenated phenolic compounds by O-methylation is mediated by both bacteria and fungi  and is thought to be an alternative pathway to degradation; however, in many instances, the function and purpose are not yet understood.

 The fate of TBBPA methyl ether metabolites is currently not known and no additional transformation or degradation of these compounds has been reported. 

However, the increased lipophilicity and decreased water solubility of these compound make them more likely to accumulate and persist in the environment. 

Notably, TBBPA DME has been detected in aquatic sediments. 

Toxicological data on this new metabolite of TBBPA are lacking, but are crucial to understanding the impact of accumulation of TBBPA DME in the environment.


Melting point     178-181 °C(lit.)

Boiling point     316 °C

density         2.1

refractive index     1.5000 (estimate)

storage temp.     2-8°C

solubility       Insoluble

pka              8.50±0.10(Predicted)

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant.

The compound is a white solid (not colorless), although commercial samples appear yellow. 

It is one of the most common fire retardants.

Production and use:

TBBPA is produced by the reaction of bromine with bisphenol A. 

Most commercial TBBPA products consist of a mixture that differ in the degree of bromination with the formula C15H16−xBrxO2 where x = 1 to 4.
Its fire-retarding properties correlate with %Br.

TBBPA is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone. 

It is used to prepare fire-resistant polycarbonates by replacing some bisphenol A. 

A lower grade of TBBPA is used to prepare epoxy resins, used in printed circuit boards.

Tetrabromobisphenol A (TBBPA) is one of the most prevalent flame retardants, and is used in plastic paints, synthetic textiles, and electrical devices. 

Despite the fact that TBBPA is excreted quickly from the body, it is detected in human plasma and milk. 

Owing to the structural resemblance to thyroid hormones (THs), the thyroid disruption activities of TBBPA have been investigated over the past two decades. 

Possible action sites are plasma TH binding protein and TH receptors. In experimental animal models, TBBPA exposure induces a decrease in plasma TH levels and a delay of TH-induced metamorphosis in animals. 

In studies using cell lines, TBBPA shows weak agonist and antagonist activities. 

These in vitro and in vivo bioassays may be powerful tools for detecting the thyroid system disruption activity of TBBPA. 

Although recent findings suggest diverse biological effects of TBBPA on the thyroid, reproductive, and immune systems, there is still controversy regarding these effects.

Toxicity:

A study was published by the European Food Safety Authority (EFSA) in December 2011 on the exposure of TBBPA and its derivatives in food. 

The study, which examined at 344 food samples from the fish and other seafood food group, concluded that “current dietary exposure to TBBPA in the European Union does not raise a health concern.”

EFSA also determined that “additional exposure, particularly of young children, to TBBPA from house dust is unlikely to raise a health concern”.

Some studies suggest that TBBPA may be an endocrine disruptor and immunotoxicant. As an endocrine disruptor, TBBPA may interfere with both estrogens and androgens.

Further, TBBPA structurally mimics the thyroid hormone thyroxin (T4) and can bind more strongly to the transport protein transthyretin than T4 does, likely interfering with normal T4 activity. 

TBBPA likely also suppresses immune responses by inhibiting expression of CD25 receptors on T cells, preventing their activation, and by reducing natural killer cell activity.

A 2013 literature review on TBBPA concludes that TBBPA does not produce “adverse effects that might be considered to be related to disturbances in the endocrine system”.

Therefore, in accordance with internationally accepted definitions, TBBPA should not be considered an “endocrine disruptor”. 

Furthermore, TBBPA is rapidly excreted in mammals and therefore does not have a potential for bioaccumulation. 

Measured concentrations of TBBPA in house dust, human diet and human serum samples are very low. 

Daily intakes of TBBPA in humans were estimated to not exceed a few ng/kg bw/day. 

Exposures of the general population are also well below the derived-no-effect-levels (DNELs) derived for endpoints of potential concern in REACH.

TBBPA degrades to bisphenol A and to TBBPA dimethyl ether, and experiments in zebrafish (Danio rerio) suggest that during development, 

TBBPA may be more toxic than either BPA or TBBPA dimethyl ether.


Occurrence:

TBBPA emits can be found in trace concentration in the hydrosphere, soil, and sediments. 

It also occurs in sewage sludge and house dust.

TBBPA has been the subject of an eight-year evaluation under the EU Risk Assessment procedure which reviewed over 460 studies.

The Risk Assessment was published on the EU Official Journal in June 2008.

The conclusions of the Risk Assessment were confirmed by the European Commission SCHER Committee (Scientific Committee on Health and Environmental Risks). 

Tetrabromobisphenol A is a white to pale cream or pale yellow crystalline with a moderately high molecular weight, low water solubility, and moderately high lipophilicity (as indicated by log Kow). 

Only about 4% of the particles are <15 μm in diameter, and thus, little (<4%) is expected to be respirable (<10 μm in diameter) and absorbed from the lung after inhalation exposure.

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant used in a variety of reactive and additive applications. It is reacted (i.e., covalently bound) with epoxy, vinyl esters, and polycarbonate systems (e.g., high impact polystyrene (HIPS), and is used as an additive in acrylonitrile-butadiene-styrene (ABS) thermoplastic resins. 

Its primary application is in printed wire boards (PWBs) as a reactive flame retardant.

Tetrabromobisphenol A is widely used as a reactive flame retardant to produce a bromine-containing epoxy resin and polycarbonate, and as intermediates for the synthesis of other complex flame retardant, 

also as an additive flame retardant for ABS, HIPS, unsaturated polyester rigid polyurethane foams, adhesives and coatings.

A bromobisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups and the phenyl rings are substituted by bromo groups at positions 2, 2', 6 and 6'. It is a brominated flame retardant.

General Description: White powder.

 A monomer for flame-retardant epoxy, polyester and polycarboante resins.

Air & Water Reactions: Insoluble in water.

Reactivity Profile: Tetrabromobisphenol A is monomer.

Hazard: Moderately toxic by inhalation and skincontact. An eye irritant.

Fire Hazard: Tetrabromobisphenol A is nonflammable.

Environmental Fate:    Its physicochemical properties suggest that it will partition to all compartments (i.e., water, sediment, and soil), predominantly to sediment and soil through binding to the organic fraction of a particulate matter. Available environmental fate studies indicated that 

TBBPA is persistent in water (half-life [t1/2] 182 days), soil (t1/2 182 days), and sediment (t1/2 365 days).

It lacks functional groups that are expected to undergo hydrolysis. 

A number of laboratory studies (ECHA, 2013) showed that it can degrade to bisphenol A under aerobic conditions.

Tetrabromobisphenol A is identified as a persistent, bioaccumulative, and toxic (PBT) compound under the U.S. Environmental Protection Agency s Toxic Release Inventory. It was also placed on the State of Washington s Department of Ecology s PBT List . 

However, Environment Canada and Health Canada concluded that TBBPA did not meet their criteria for bioaccumulation (i.e., bioaccumulation factor >5000). 

This conclusion was based on TBBPA s low bioaccumulation potential from its physicochemical properties (e.g., maximum diameter of 1.3 1.4 nm, ionization at environmentally relevant pH, and variable logKOW), 

as well as from studies that showed TBBPA is rapidly metabolized and excreted in aquatic and terrestrial organisms.

EMERGENCY OVERVIEW:

Causes eye, skin, and respiratory tract irritation. Target Organs: Respiratory system, eyes, skin.

Potential Health Effects

Eye: Causes eye irritation.

Skin: Causes skin irritation.

Ingestion: May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.

Inhalation: Causes respiratory tract irritation.

Chronic: Adverse reproductive effects have been reported in animals.

Handling and Storage:

Minimize dust generation and accumulation.

Avoid breathing dust, mist, or vapor.

Avoid contact with eyes, skin and clothing. 

Keep container tightly closed. 

Avoid ingestion and inhalation. 

Use only in a chemical fume hood.

Wash clothing before reuse.

Storage: Store in a cool, dry place. Store in a tightly closed container.
 

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