79755-43-4

Basic information

• Product Name: 6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER
• Synonyms: 6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER;3,5-dibromo-2-(2,4-dibromophenoxy)phenol
• CAS NO: 79755-43-4
• Molecular Formula: C₁₂H₆Br₄O₂
• Molecular Weight: 501.79084
• Mol File: 79755-43-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 171-172 °C
• Boiling Point: 405.9°C at 760 mmHg
• Flash Point: 199.3°C
• Appearance: /
• Density: 2.248g/cm³
• Vapor Pressure: 3.6E-07mmHg at 25°C
• Refractive Index: 1.69
• PKA: 6.80±0.40(Predicted)
• CAS DataBase Reference: 6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER(79755-43-4)
• EPA Substance Registry System: 6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER(79755-43-4)

Safety Data

• Hazardous Substances Data: 79755-43-4(Hazardous Substances Data)

Usage

General Description

6-HYDROXY-2,2',4,4'-TETRABROMODIPHENYL ETHER, also known as BDE-153, is a chemical compound belonging to the class of polybrominated diphenyl ethers (PBDEs). PBDEs are used as flame retardants in consumer products such as electronics, textiles, and plastics. BDE-153 has been found to be persistent in the environment and has the potential to bioaccumulate in organisms. It is also known to have toxic effects on the endocrine and reproductive systems, as well as potential neurotoxic and developmental effects. As a result, BDE-153 has been subject to regulatory restrictions and bans in many countries. Efforts are being made to mitigate its presence in the environment and to find safer alternatives for flame retardant applications.

InChI:InChI=1/C12H6Br4O2/c13-6-1-2-11(8(15)3-6)18-12-9(16)4-7(14)5-10(12)17/h1-5,17H

Upstream product

• 102739-99-1 6-methoxy-6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether 

Downstream Products

• 1695-04-1 2-methoxyphenyl phenyl ether 
• 497106-81-7 5-chloro-6-methoxy-2,2',4,4'-tetrabromodiphenyl ether 
• 297742-10-0 2-(2’,4’-dibromophenoxy)-3,5,6-tribromophenol 
• 102739-99-1 6-methoxy-6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether 
• 80246-31-7 Acetic acid 3,5-dibromo-2-(2,4-dibromo-phenoxy)-phenyl ester 

Relevant articles and documents

Synthesis of hydroxylated and methoxylated polybrominated diphenyl ethers - Natural products and potential polybrominated diphenyl ether metabolites

Hydroxylated and methoxylated polybrominated diphenyl ethers (OH-PBDEs and MeO-PBDEs) may be natural products or they may be formed as metabolites of polybrominated diphenyl ethers (PBDEs), frequently used as flame retardants. The aim of this work was to synthesize authentic OH- and MeO-PBDE reference standards for analytical and toxicological studies. Brominated phenoxybenzaldehydes were prepared either by coupling of 2,4-dibromophenol with various fluorobenzaldehydes or by coupling of brominated hydroxybenzaldehydes with 2,2′,4,4′-tetrabromodiphenyliodonium chloride. OH-PBDEs were synthesized via the brominated phenoxybenzaldehydes by Baeyer-Villiger oxidation and acid-catalyzed hydrolysis. These OH-PBDEs were ortho- and para-brominated (relative to the hydroxy group) with benzyltrimethylammonium tribromide and/or orthobrominated with bromine/tert-butylamine, and were also brominated with bromine in one case. MeO-PBDEs were obtained by methylation of the prepared OH-PBDEs. MeO-PBDEs were also prepared through the coupling of brominated methoxyphenols with 2,2′,4,4′-tetrabromodiphenyliodonium salts, the corresponding OH-PBDEs being obtained after demethylation. A majority of the OH-/MeO-PBDEs prepared have the hydroxy/methoxy group in the ortho position relative to the diphenyl ether bond. All OH-/MeO-PBDEs prepared have 2,4-dibromo substitution patterns (relative to the diphenyl ether bond) in the non-hydroxy-/non-methoxy-containing ring. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.