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Bis(2-ethylhexyl) tetrabromophthalate, is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).
Bis(2-ethylhexyl) tetrabromophthalate is the diester of tetrabromophthalic acid and (racemic) 2-ethylhexanol.
Bis(2-ethylhexyl) tetrabromophthalate has two stereocenters, located at the carbon atoms carrying the ethyl groups.
CAS Number: 26040-51-7
Molecular Formula: C24H34Br4O4
Molecular Weight: 706.14
EINECS Number: 247-426-5
Synonyms: bis(2-ethylhexyl) 3,4,5,6-tetrabromophthalate, Bis(2-ethylhexyl) tetrabromophthalate, Pyronil 45, 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, 1,2-bis(2-ethylhexyl) ester, DP 45, UNII-413M0N3V1G, DTXSID7027887, HSDB 8216, Bis(2-ethyhexyl) tetrabromophthalate, Di(2-ethylhexyl) Tetrabromophthalate, EINECS 247-426-5, bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate, Phthalic acid, tetrabromo-, bis(2-ethylhexyl) ester, 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, bis(2-ethylhexyl) ester, Bis(2-ethyl-1-hexyl) Tetrabromophthalate, DTXCID507887, FRP 45, EC 247-426-5, Phthalic acid, tetrabromo-, di(2-ethylhexyl) ester, 247-426-5, 26040-51-7, TBPH, bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate, 413M0N3V1G, C24H34Br4O4, di(2-ethylhexyl)tetrabromophthalate, bis(2-ethylhexyl)tetrabromophthalate, MFCD01941091, Bis(2-ethylhexyl)3,4,5,6-tetrabromophthalate, SCHEMBL2729914, CHEMBL3188536, Tox21_302404, AKOS016009450, CS-W019373, DS-5244, s11887, NCGC00255235-01, CAS-26040-51-7, DB-100907, NS00005572, bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate, Q19931407, 1,2-BIS(2-ETHYLHEXYL) 3,4,5,6-TETRABROMOPHTHALATE, Bis(2-ethylhexyl) 3 pound not4 pound not5 pound not6-tetrabromophthalate, Bis(2-ethylhexyl) 3,4,5,6-tetrabromophthalate 100 microg/mL in Hexane, 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, bis(2-ethylhexyl) ester;bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate;Bis(2-ethylhexyl)tetrabromphthalat;2-benzenedicarboxylic acid, 3,4,5,6-tetrabromo-bis(2-ethylhexyl) ester;Phthalic acid, tetrabromo-, di(2-ethylhexyl) ester;Phthalic acid,tetrabromo-,di(2-ethylhexyl)ester;3,4,5,6-Tetrabromo-1,2-benzenedicarboxylic acid dioctyl ester;tetrabromophthalic acid bis(2-ethylhexyl) ester
Bis(2-ethylhexyl) tetrabromophthalate is the diester of tetrabromophthalic acid and 2-ethylhexanol, meaning its structure is based on a phthalate backbone that has been modified with four bromine atoms and two ethylhexyl groups, making it both lipophilic and bromine-rich.
In laboratory conditions, Bis(2-ethylhexyl) tetrabromophthalate has been shown to undergo photolytic degradation in solvents when exposed to UV radiation, likely via sequential reductive debromination.
Furthermore, the dominant products of this degradation are di- and tribrominated analogues of TBPH (most of which were also missing both alkane branches).
As a result, it has three distinct stereoisomers, consisting of an (R,R) form, an (S,S) form (diastereomers), and a meso (R,S) form.
Bis(2-ethylhexyl) tetrabromophthalate is the brominated analogue of bis(2-ethylhexyl) phthalate (DEHP).
Much like Bis(2-ethylhexyl) tetrabromophthalate, DEHP has been widely used as a plasticizer, however unlike TBPH, it is currently a restricted substance due to its endocrine disrupting properties and reproductive toxicity.
Although the structural similarity to DEHP raises some concern for toxicity of TBPH, bromination alters the physical and chemical properties of DEHP.
Additionally, Bis(2-ethylhexyl) tetrabromophthalate shares many similar structural characteristics (e.g., aromatic rings, bromination) with a class of BFRs called polybrominated diphenyl ethers (PBDEs) which has faced a great deal of attention and numerous restrictions due to their persistence, bioaccumulation, and potential toxicity.
These structural similarities have brought up concerns that it may behave similarly to PBDEs in the environment.
Bis(2-ethylhexyl) tetrabromophthalate is reportedly stable under normal conditions of handling and use.
Thermal decomposition may produce hydrogen bromide and/or bromine and carbon oxides such as carbon monoxide and carbon dioxide.
Additionally, halogenated compounds with aromatic rings (such as TBHF) can degrade into dioxins and dioxin-like compounds, particularly when heated.
Their halogenated-counterparts, chlorinated dioxins, are among the highly toxic compounds listed by the Stockholm Convention on Persistent Organic Pollutants.
Bis(2-ethylhexyl) tetrabromophthalate is a brominated flame retardant chemical compound that is primarily used to reduce the flammability of plastics, foams, and other polymer materials, particularly in commercial and industrial products where fire resistance is essential.
Although no specific structures for these degradation products have been confirmed, this breakdown pattern remains of some concern.
As a general rule, PDBEs with higher numbers of bromine atoms, such as decaBDE, are less toxic than PBDEs with lower numbers of bromine atoms, such as pentaBDE.
However, as higher-order PBDEs degrade, bromine atoms are removed, resulting in more toxic PBDE congeners.
The lower brominated PBDE congeners formed as a result of debromination are generally more persistent, bioaccumulative, and toxic.
Reductive debromination could produce TBPH’s debrominated analogue DEHP, a common plasticizer. However, this has not been confirmed.
Although this indicates that Bis(2-ethylhexyl) tetrabromophthalate can be photolytically degraded, the process is slower than for other PBDEs, such as decaBDE or nonaBDEs.
This suggests that TBPH may be more persistent, at least photolytically, than higher brominated PBDEs congeners in the environment.
This is supported by its very low vapour pressure, which suggests photolysis in the atmosphere is not considered to be a relevant degradation pathway.
Bis(2-ethylhexyl) tetrabromophthalate is a high-molecular-weight organic compound, categorized within the broader family of organobromine compounds and phthalate esters.
The presence of multiple bromine atoms on the aromatic ring is what gives it its flame-retardant properties, as these atoms interfere with combustion reactions by quenching free radicals and slowing the spread of flames.
The two ethylhexyl side chains make the molecule more soluble in polymers and oils, allowing it to be easily blended into flexible plastics and rubber-based materials.
Bis(2-ethylhexyl) tetrabromophthalate was first introduced to the market as a brominated component of the commercial fire retardant mixtures Firemaster 550 (FM 550), BZ 54, and DP-45, all of which are manufactured by Chemtura Corp (West Lafayette, IN).
The mixture which would eventually become known as FM 550, was first reported to the USEPA in 1995 by Chemtura.
In 1997, Chemtura entered into a Consent Order with USEPA allowing the introduction into commerce.
At the time, it was presented as a less persistent and less likely to bioaccumulate alternative to pentaBDE, a commercial PBDE mixture which would later be banned in Europe, and voluntarily phased out in the United States in 2004.
Despite the phaseout, between 2001 and 2008, the production volume of brominated flame retardants worldwide doubled from approximately 200,000 to 410,000 metric tons (mt) annually.
In the absence of exact sales numbers for FM 550, a 2011 study would find the mixture as the second most commonly detected flame retardant in polyurethane foam used and sold in the United States.
Contrary to public declarations made by USEPA officials in 2003, documents obtained by the Chicago Tribune showed that scientists within the agency were deeply skeptical about the safety of FM 550.
Due to its use as an additive (as opposed to a reactive, e.g. covalently bound), as well as similarities in structure and properties to PBDEs, environmental fates similar to PentaBDE were expected.
Owing to these concerns, Chemtura entered into a modified Consent Order with USEPA in 2008, which required further testing of FM 550.
In the meantime, the contents of the mixture remained unknown to the wider scientific community until 2008, when a study by Stapleton et al. found two new chemicals with high levels of bromine while analyzing dust samples from homes in Boston.
Stapleton analyzed the substance and confirmed the presence of four different components: triphenyl phosphate (TPP); a mixture of isopropylated triphenyl phosphate isomers (ITPs); 2-ethylhexyl-2,3,4,5-tertrabromobenzoate (TBB); and bis(2-ethylhexyl) tetrabromophthalate (TBPH), in the FM 550 mixture as well as the dust samples.
By 2012, studies measuring flame retardant levels in the environment had detected both TBB and Bis(2-ethylhexyl) tetrabromophthalate in indoor dust, outdoor air, marine mammal tissues, and wastewater sewage sludge, suggesting that, like some of their pentaBDE predecessors, these chemicals were indeed leaching from treated products and entering the environment.
The year 2015 saw re-assessments of the chemical in both the United States as the European Union.
In the United States, the USEPA assessed a group of seven brominated phthalates, including Bis(2-ethylhexyl) tetrabromophthalate, for problem formulation and data needs assessment.
However, it was concluded that the available data on the toxicological hazard of these chemicals is incomplete for risk assessment.
At the same time, a testing proposal evaluation was performed in the European Union, which resulted in a request for a prenatal developmental toxicity study.
A compliance check (the testing of products manufactured, imported or retailed in the European Union against REACH Regulation) was performed in 2016 with requests for further study, which were provided, and accepted by ECHA.
In line with this investigation, the registration of Bis(2-ethylhexyl) tetrabromophthalate was updated with assessments of the potential endocrine disrupting properties of the substance for the environment and human health.
Following the compliance check, Bis(2-ethylhexyl) tetrabromophthalate was included in a Community Rolling Action Plan (CoRAP) for evaluation in March 2019 by the Swedish Chemicals Agency (KEMI) in order to clarify concerns related to wide dispersive use; exposure of environment; potential endocrine disrupting; and persistence, bioaccumulation and toxicity (PBT) or very persistent and very bioaccumulative (vPvB) properties.
The evaluation confirmed suspected vPvB properties, leading to its inclusion on ECHA’s PBT assessment list.
Following the confirmation of vPvB properties, KEMI considered it appropriate to prepare and submit a substance of very high concern (SVHC) dossier.
Bis(2-ethylhexyl) tetrabromophthalate is used to investigate the inuence of environmentally relevant dose of DEHP on adipogenesis in the human cell culture model SGBS.
Bis(2-ethylhexyl) tetrabromophthalate is can be used to study the quantify indoor phthalate ester degradation through both biotic and abiotic mechanisms.
Bis(2-ethylhexyl) tetrabromophthalate is a ubiquitous environmental contaminant, but its toxicity is not fully understood.
Bis(2-ethylhexyl) tetrabromophthalate had biphasic elimination behavior where 94% of the body burden was depleted within the rst 12 h of elimination and the remaining 6% eliminated very slowly thereafter (half-life of 15 days).
There was little evidence for biotransformation of either chemical.
This investigation conrms the extremely hydrophobic behavior of Bis(2-ethylhexyl) tetrabromophthalate and its impact on its bioavailability.
Bis(2-ethylhexyl) tetrabromophthalate has been used as a replacement in some commercial ame-retardant mixtures.
Bis(2-ethylhexyl) tetrabromophthalate is widely used in industrial products, so the probability of human exposure to TBPH is high.
Bis(2-ethylhexyl) tetrabromophthalate is known about how it is metabolized or its toxicity.
To this end, we investigated what eect oral exposure to Bis(2-ethylhexyl) tetrabromophthalate at concentrations of 200 mg kg−1 had on hepatic damage.
Boiling point: 584.8±45.0 °C(Predicted)
Density: 1.529±0.06 g/cm3(Predicted)
vapor pressure: 0Pa at 25℃
storage temp.: Sealed in dry,2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Oil
color: Colourless to Pale Yellow
Water Solubility: 794μg/L at 20℃
LogP: 10.2 at 25℃
Bis(2-ethylhexyl) tetrabromophthalate is synthesized by a process known as the Wittig reaction, involving the reaction of an aldehyde or ketone with an organophosphorus compound to form an alkene.
Bis(2-ethylhexyl) tetrabromophthalate is produced by the reaction of tetrabromophthalic anhydride with racemic 2-ethylhexanol in the presence of titanium isopropoxide catalyst via a general synthesis method widely applied to the technical field of flame retardant synthesis.
Synthesis of Bis(2-ethylhexyl) tetrabromophthalate from tetrabromophthalic anhydride and 2-ethylhexanol.
In this general synthesis method, tetrabromophthalic anhydride and 2-ethylhexanol are used as raw materials in a molar mass ratio of 3-7:1.
Nitrogen is introduced as an inert protective gas, and the direct diesterification of tetrabromophthalic anhydride is achieved by using an organic base (preferably ammonia water, triethylamine, di-n-butylamine or ethylenediamine) as a neutralizing agent to remove the residual sulfuric acid in the system, with titanium tetrachloride as a catalyst.
The reaction proceeds at 200-230 °C under reflux to rapidly separate the water formed during the reaction.
The catalyst is removed by pickling, and the solvent distilled under reduced pressure to obtain a crude product.
Decolorization and impurity removal is achieved by adding hydrogen peroxide; a composite decolorizer consisting of activated carbon, diatomaceous earth and adsorption resin; and a diluent such as methanol, ethanol, n-propanol, isopropanol or n-butanol.
After removing the composite by filtration, the light-colored product Bis(2-ethylhexyl) tetrabromophthalate is obtained by distilling off the diluent.
Bis(2-ethylhexyl) tetrabromophthalate is a mixture of three isomeric organic chemical compounds with the empirical formula C 24 H 34 Br 4 O 4 , which is used as a ame retardant.
Bis(2-ethylhexyl) tetrabromophthalate is the diester of tetrabromophthalic acid and 2-ethylhexanol.
Bis(2-ethylhexyl) tetrabromophthalate, a replacement for restricted ame retardants, has become ubiquitous in the environment.
To reveal the neurotoxicity and underlying mechanism of Bis(2-ethylhexyl) tetrabromophthalate, we rst evaluated its penetrability through the blood-brain barrier (BBB) using hCMEC/D3 cells as in vitro model, and found TBPH had poor penetrability through BBB with a maximum Papp of 14.8 × 10−6 cm s−1.
In vitro mutagenicity tests have shown that TBPH can induce chromosomal aberrations, but does not give rise to point mutations.
Bis(2-ethylhexyl) tetrabromophthalate is suspected that TBPH is not genotoxic in vivo.
Although carcinogenicity tests have not been assessed for Bis(2-ethylhexyl) tetrabromophthalate, (Q)SAR predictions did show that TBPH, belonging to the phthalates/benzoate group, has positive indications for being carcinogenic.
Sub-acute and sub-chronic toxicity tests have demonstrated that Bis(2-ethylhexyl) tetrabromophthalate causes minimal toxicity and no treatment-related effects, respectively.
The no-observed-adverse-effect level (NOAEL) of a mixture containing TBPH is 50 mg/kg/day.
Bis(2-ethylhexyl) tetrabromophthalate is classified as GHS hazard statement H319, so it can lead to serious eye irritation.
According to the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) Annex XIII criteria, TBPH is a very persistent and very bio-accumulative (vPvB) compound.
Even though Bis(2-ethylhexyl) tetrabromophthalate is poorly absorbed and metabolised, and rapidly eliminated unchanged via faeces, studies have shown that it still has potential to accumulate in adrenal and liver tissue.
Additionally, accumulation of a Firemaster 550, a mixture containing TBPH, was observed in placentas of rats.
Bis(2-ethylhexyl) tetrabromophthalateacted as an antagonist in a yeast estrogen/androgen screening assays (YES and YAS assays), suggesting it may affect reproduction.
However, the potential of Bis(2-ethylhexyl) tetrabromophthalate to cause reproductive or developmental problems has only been studied using TBPH in a mixture with other fire retardants and is therefore inconclusive.
Bis(2-ethylhexyl) tetrabromophthalate is the non-brominated version of TBPH and currently a restricted substance because it is an endocrine disruptor for human health and environment.
It has been shown that DEHP can affect reproduction and development.
Bis(2-ethylhexyl) tetrabromophthalate is a potential endocrine disruptor due to the similarity between TBPH and DEHP. However, there is limited evidence TBPH gets debrominated or metabolised to DEHP in vivo.
Studies using human vascular endothelial cells (HUVECs) demonstrated that the Bis(2-ethylhexyl) tetrabromophthalate metabolite TBMEHP is more toxic than TBPH itself, since it inhibited cell growth, and induced cell cycle arrest and apoptosis.
Still, the metabolism of DEHP to its toxic metabolite (MEHP) is approximately 100 times faster than the metabolism of TBPH to TBMEHP.
Data on Firemaster 550 observed weight gain, reduced liver enzyme activity, and thyroid hormone axis disruption upon exposure.
Since this is a mixture containing Bis(2-ethylhexyl) tetrabromophthalate and other fire retardants, it remains unclear what components have the endocrine disrupting potential.
Although in vitro data provides indications that TBPH may have endocrine disrupting properties, in vivo data cannot confirm this.
In a combustion scenario, Bis(2-ethylhexyl) tetrabromophthalate works by decomposing into free radicals and hydrogen bromide, which interfere with the heat and flame propagation mechanisms.
This helps suppress ignition and reduce smoke and heat release, providing more time for escape in fire emergencies and reducing the risk of property damage.
Bis(2-ethylhexyl) tetrabromophthalates high thermal stability allows it to function effectively in high-temperature processing environments such as those used in plastic manufacturing.
Bis(2-ethylhexyl) tetrabromophthalate is often included in commercial flame retardant formulations, such as Firemaster 550, which contains a blend of chemicals used in polyurethane foam for consumer products.
In such mixtures, Bis(2-ethylhexyl) tetrabromophthalate may be combined with other flame retardants or synergists (e.g., organophosphates) to improve overall fire resistance and compatibility with various polymers.
Uses:
Bis(2-ethylhexyl) tetrabromophthalate is predominantly used as a non-reactive (additive) brominated flame retardant, meaning it is physically blended into materials without chemically bonding to them, allowing manufacturers to enhance the fire resistance of a wide variety of polymer-based products.
Its molecular structure, which includes four bromine atoms on a phthalate core, allows it to effectively interfere with combustion processes by releasing bromine radicals that quench flames and slow down the spread of fire, making it a valuable ingredient for products that need to meet stringent fire safety regulations.
One of the most widespread uses of Bis(2-ethylhexyl) tetrabromophthalate is in the production of flexible polyurethane foam, a material commonly found in upholstered furniture, mattresses, car seats, and infant products such as changing pads or play mats.
By incorporating Bis(2-ethylhexyl) tetrabromophthalate into these foams, manufacturers are able to comply with flammability standards such as California Technical Bulletin 117, which historically required certain levels of fire resistance in consumer furnishings, particularly in the United States.
Bis(2-ethylhexyl) tetrabromophthalate is a brominated phthalate derivative used in flame-retardant polyvinyl chloride compositions.
In the automotive sector, Bis(2-ethylhexyl) tetrabromophthalate is used in various components that require flame retardancy, including seat cushions, insulation panels, dashboards, door panels, and carpeting.
Because vehicles often contain large amounts of polymeric materials in confined spaces, flame retardants like Bis(2-ethylhexyl) tetrabromophthalate help reduce the risk of fire propagation in the event of an electrical fault, overheating, or crash.
This enhances passenger safety and contributes to vehicle manufacturers meeting transportation safety standards.
Although Bis(2-ethylhexyl) tetrabromophthalate is primarily known for its flame-retardant function, its structural similarity to phthalates means it can also act as a secondary plasticizer in some applications, helping to increase flexibility, durability, and workability of certain plastics.
However, this dual function is considered incidental, and the flame retardant properties are generally its main value in formulations.
As an additive, Bis(2-ethylhexyl) tetrabromophthalate improves the flame retardancy of plastics, and acts as a flow promoter, which improves the molding properties of plastic formulations, and facilitates the processing of plastics without other adverse side effects.
As such, it is widely used as a fire retardant and plasticizer in a variety of thermoplastic and thermosetting plastics, such as HIPS, ABS, PU, epoxy, PVC, modified PPO, PC, Polybutylene terephthalate and unsaturated polyester for use in wire and cable insulation, film and sheeting, carpet backing, coated fabrics, wall coverings and adhesives.
As opposed to reactive components, which are bound to a polymer material by a chemical reaction when the material is being created, additives are blended with or coated on materials to make them flame resistant.
As a result, additives are not chemically bonded to the base material and leach out more easily.
Historically, Bis(2-ethylhexyl) tetrabromophthalate has been found in a wide array of consumer goods, including office chairs, strollers, electronics, baby carriers, and insulation materials.
Although some manufacturers have phased it out due to health and environmental concerns, it still persists in older products, and its continued use in specific sectors makes it a legacy contaminant of interest in studies of indoor dust and human exposure.
In addition to its use as a flame retardant, it is reportedly also used as a broad-spectrum synthetic pyrethroid insecticide under the name Pyronil 45-d34.
Bis(2-ethylhexyl) tetrabromophthalate is effective against a variety of insect pests, including mosquitoes, flies, fleas, and ticks.
However, its use as an insecticide is under-reported, and limited to a mention by the American Chemical Supplier BenchChem.
Release to the environment of Bis(2-ethylhexyl) tetrabromophthalate can occur from industrial use: of articles where the substances are not intended to be released and where the conditions of use do not promote release.
Other release to the environment of Bis(2-ethylhexyl) tetrabromophthalate is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Bis(2-ethylhexyl) tetrabromophthalate can be found in complex articles, with no release intended: machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines).
Bis(2-ethylhexyl) tetrabromophthalate can be found in products with material based on: rubber (e.g. tyres, shoes, toys) and plastic (e.g. food packaging and storage, toys, mobile phones).
Bis(2-ethylhexyl) tetrabromophthalateis used in the following products: adhesives and sealants and polymers.
Bis(2-ethylhexyl) tetrabromophthalate is used in the following areas: building & construction work and scientific research and development.
Other release to the environment of Bis(2-ethylhexyl) tetrabromophthalate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Bis(2-ethylhexyl) tetrabromophthalate is often included in commercial flame retardant mixtures, most notably in a proprietary blend known as Firemaster 550, which is used to treat polyurethane foams and other materials that need enhanced thermal stability and flame resistance.
In these formulations, Bis(2-ethylhexyl) tetrabromophthalate is usually combined with other flame retardants such as Bis(2-ethylhexyl) tetrabromophthalate or organophosphate esters to provide synergistic flame-retardant performance across a wider range of materials and combustion scenarios.
Bis(2-ethylhexyl) tetrabromophthalate may also be used to treat coated fabrics, curtains, wall coverings, carpet backings, and construction materials where added flame retardancy is required to meet building codes or safety regulations.
In these applications, Bis(2-ethylhexyl) tetrabromophthalate helps ensure that materials used in residential, commercial, and public buildings do not easily ignite or contribute significantly to fire growth during an emergency.
Bis(2-ethylhexyl) tetrabromophthalate is used in the following products: polymers and adhesives and sealants.
Release to the environment of Bis(2-ethylhexyl) tetrabromophthalate can occur from industrial use: formulation of mixtures and formulation in materials.
Bis(2-ethylhexyl) tetrabromophthalate is used in the following products: adhesives and sealants and polymers.
Bis(2-ethylhexyl) tetrabromophthalate is used for the manufacture of: plastic products and rubber products.
Release to the environment of Bis(2-ethylhexyl) tetrabromophthalate can occur from industrial use: in the production of articles and in processing aids at industrial sites.
Bis(2-ethylhexyl) tetrabromophthalate is a versatile and effective flame retardant that is used across multiple industries, including furniture, automotive, electronics, construction, and textiles, to reduce the risk of fire and enhance material performance in flammable environments.
Its compatibility with flexible plastics and its high thermal stability make it especially useful in applications where fire prevention is a regulatory and safety priority.
Bis(2-ethylhexyl) tetrabromophthalate is used as a flame retardant in flexible polyurethane foam, neoprene, rubber, appliances, and construction and electrical materials.
2011 study detected Bis(2-ethylhexyl) tetrabromophthalate or TBB in various children’s products including car seats, changing table pads, portable mattresses and rocking chairs.
Bis(2-ethylhexyl) tetrabromophthalate is a component of the widely used fire-retardant mixture Firemaster 550 (FM 550).
Bis(2-ethylhexyl) tetrabromophthalate is also a component of the commercial fire-retardant mixture DP 45.
Bis(2-ethylhexyl) tetrabromophthalate is also added to wire and cable insulation materials, especially in polyvinyl chloride (PVC) and similar thermoplastics, to prevent ignition and reduce smoke production in the case of electrical short circuits or overheating.
In electronic casings, appliance housings, and printed circuit boards, Bis(2-ethylhexyl) tetrabromophthalate can be used either alone or in flame retardant blends to suppress combustion and improve the fire performance of electronic devices, such as computers, televisions, and power strips.
Safety Profile:
Bis(2-ethylhexyl) tetrabromophthalate is a lipophilic (fat-loving) compound, which means it can be absorbed through the skin, especially through prolonged or repeated contact with treated materials such as foam cushions or dust.
Once inside the body, it tends to accumulate in fatty tissues, where it may persist for long periods.
Some studies suggest Bis(2-ethylhexyl) tetrabromophthalate may act as a bioaccumulative substance, though its behavior in the human body is still being investigated.
Preliminary toxicological evidence suggests that Bis(2-ethylhexyl) tetrabromophthalate may interfere with the endocrine system, which regulates hormones responsible for growth, reproduction, and metabolism.
Exposure to Bis(2-ethylhexyl) tetrabromophthalate in animal models has been linked to altered reproductive organ development, reduced sperm quality, and disruptions in estrogen and androgen activity.
Although more conclusive research is needed, these findings have prompted regulators to monitor its potential role as an endocrine disruptor.
Bis(2-ethylhexyl) tetrabromophthalate-containing products break down over time or are exposed to heat, they can release fine particles or dust containing TBPH into indoor air.
Inhalation of these particles—especially in poorly ventilated areas or in occupational settings—may cause irritation of the respiratory tract, and prolonged exposure has raised concerns about potential impacts on lung health, although more research is needed to determine the extent of this risk.
Because Bis(2-ethylhexyl) tetrabromophthalate shares structural similarities with DEHP, a phthalate known for its endocrine-disrupting and developmental toxic effects, researchers have expressed concern that TBPH may have similar neurodevelopmental impacts, particularly in infants and young children.
Animal studies and in vitro experiments have shown possible disruptions to hormone activity, though human data remains limited.
The potential for neurological, behavioral, or cognitive impacts due to chronic exposure—especially in vulnerable populations—is a growing area of study.
