2,2',4,4'-TETRABROMODIPHENYL ETHER Chemical Properties

Melting point:

83-84℃ (ethanol )

Boiling point:

396 °C

Density 

2.161±0.06 g/cm3(Predicted)

Flash point:

-12 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Methanol: Soluble

form 

Solid

color 

White to off-white

InChI

InChI=1S/C12H6Br4O/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6H

InChIKey

XYBSIYMGXVUVGY-UHFFFAOYSA-N

SMILES

C1(OC2=CC=C(Br)C=C2Br)=CC=C(Br)C=C1Br

EPA Substance Registry System

Benzene, 2,4-dibromo-1-(2,4-dibromophenoxy)- (5436-43-1)

Safety Information

Hazard Codes 

F,Xn,N

Risk Statements 

11-38-50/53-65-67

Safety Statements 

60-61-62-33-29-16-9

RIDADR 

UN 1262 3/PG 2

WGK Germany 

2

2,2',4,4'-TETRABROMODIPHENYL ETHER Usage And Synthesis

Uses

2,4,2'',4''-Tetrabromodiphenyl Ether, is one of the Polybrominated di-Ph ethers (PBDEs), which are a new class of global, persistent, and toxic contaminants. It is used as Brominated flame retardants (BFRs) in various consumer products. One of the new POPs under the Stockholm Convention

Definition

ChEBI: 2,2',4,4'-Tetrabromodiphenyl ether is an organobromine compound and an aromatic ether.

Synthesis

The general procedure for the synthesis of 2,2,4,4-tetrabromodiphenyl ether using 2,4-dibromophenol as starting material: SiO2-ZrO2 (0.05 g) and 2,4-dibromophenol (2.50 g) were placed in a mortar and fully ground for 12 min. After the reaction was completed, n-pentane was used as eluent, and the reaction mixture was separated and purified by silica gel column chromatography, resulting in 2.16 g of white solid product in 89% yield.

References

[1] Patent: CN106957218, 2017, A. Location in patent: Paragraph 0043-0047
[2] AHMED KHALIL. Developmental Exposure to 2,2',4,4'-Tetrabromodiphenyl Ether Permanently Alters Blood-Liver Balance of Lipids in Male Mice.[J]. Frontiers in Endocrinology, 2018: 548. DOI: 10.3389/fendo.2018.00548
[3] XIAOJUAN CHEN. BDE-47 disrupts axonal growth and motor behavior in developing zebrafish[J]. Aquatic Toxicology, 2012, 120: Pages 35-44. DOI: 10.1016/j.aquatox.2012.04.014
[4] CATHRINE THOMSEN*. Changes in Concentrations of Perfluorinated Compounds, Polybrominated Diphenyl Ethers, and Polychlorinated Biphenyls in Norwegian Breast-Milk during Twelve Months of Lactation[J]. Environmental Science and Technology, 2010, 44 24: 9550-9556. DOI: 10.1021/es1021922
[5] CHE-JUNG CHANG . Serum concentrations of polybrominated biphenyls (PBBs), polychlorinated biphenyls (PCBs) and polybrominated diphenyl ethers (PBDEs) in the Michigan PBB Registry 40 years after the PBB contamination incident[J]. Environment International, 2020, 137: Article 105526. DOI: 10.1016/j.envint.2020.105526

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