14400-94-3

Basic information

• Product Name: 2,3,4,6-TETRABROMOPHENOL
• Synonyms: 2,3,4,6-TETRABROMOPHENOL
• CAS NO: 14400-94-3
• Molecular Formula: C₆H₂Br₄O
• Molecular Weight: 409.69548
• Mol File: 14400-94-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 113.5°C
• Boiling Point: 308.9°Cat760mmHg
• Flash Point: 140.6°C
• Appearance: /
• Density: 2.6462 (rough estimate)
• Vapor Pressure: 0.000363mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: 2,3,4,6-TETRABROMOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRABROMOPHENOL(14400-94-3)
• EPA Substance Registry System: 2,3,4,6-TETRABROMOPHENOL(14400-94-3)

Safety Data

• Hazardous Substances Data: 14400-94-3(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetrabromophenol is a chemical compound derived from phenol, characterized by the presence of four bromine atoms attached to its molecular structure. It is recognized for its flame retardant properties, which have led to its widespread use in various industries, despite its classification as a Persistent Organic Pollutant (POP) and its potential adverse effects on the environment and aquatic life.

Uses

Used in Plastics Industry:
2,3,4,6-Tetrabromophenol is used as a flame retardant additive in the plastics industry to enhance the fire resistance of various plastic products. Its chemical structure allows it to slow down the combustion process, thereby improving the safety of plastic materials.
Used in Textile Industry:
In the textile industry, 2,3,4,6-Tetrabromophenol is utilized as a flame retardant to treat fabrics and fibers, providing them with increased resistance to fire. This is particularly important for applications in upholstery, carpets, and other materials that may be exposed to fire hazards.
Used in Foam Materials:
2,3,4,6-Tetrabromophenol is also employed as a flame retardant in the production of foam materials, such as those used in furniture, mattresses, and insulation. Its incorporation into these products helps to reduce the risk of fire and improve overall safety.
However, due to the environmental and health concerns associated with 2,3,4,6-Tetrabromophenol, including its toxicity to aquatic organisms, bioaccumulation potential, and suspected endocrine-disrupting properties, many countries have implemented restrictions or bans on its use in certain products. As a result, there is a growing need for the development of safer and more environmentally friendly alternatives to 2,3,4,6-Tetrabromophenol for use in flame retardant applications.

InChI:InChI=1/C6H2Br4O/c7-2-1-3(8)6(11)5(10)4(2)9/h1,11H

Upstream product

• 67915-26-8 N-(5-hydroxy-2-nitrophenyl)acetamide 
• 585-34-2 3-tert-butylphenyol 
• 591-20-8 3-Bromophenol 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 108-95-2 phenol 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 3147-55-5 3,5-dibromosalicylic acid 
• 608-71-9 Pentabromophenol 
• 855429-70-8 2,4,5-tribromophenyl acetate 
• 126369-25-3 4,4'-(ethane-1,1-diyl)bis(2,6-dibromophenol) 
• 855836-52-1 3-bromo-2-iodophenol 
• 57688-20-7 2,3,5-tribromo-6-hydroxy-benzoic acid 
• 858855-11-5 5-bromo-2-iodo-phenol 

Downstream Products

• 608-71-9 Pentabromophenol 
• 25779-26-4 2,3,5-tribromo-1,4-benzoquinone 
• 14401-61-7 2,4,5-tribromophenol 
• 858832-42-5 2,3,4-tribromo-6-nitro-phenol 
• 95970-07-3 2,3,4,6-tetrabromoanisole 
• 108-93-0 cyclohexanol 
• 591-20-8 3-Bromophenol 
• 207122-16-5 2,3,4,6-tetrabromophenyl 2,4,5-tribromophenyl ether 
• 95970-10-8 2,4,5-tribromo-anisole 
• 34946-84-4 hexabromo-cyclohexa-2,5-dienone 
• 815578-59-7 3,4,6-tribromo-2-nitro-phenol 
• 725714-49-8 3,4,6-tribromo-2-nitro-anisole 
• 124337-19-5 (2,3,4,6-tetrabromophenyl)-2,2,3,4,4-pentafluoro-3,4-dibromo-butyrate 

Relevant articles and documents

A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.

Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma

A growing number of studies have reported phenolic halogenated compounds (PHCs) that are retained in the blood of humans and wildlife. These PHCs may be industrial chemicals; metabolites thereof, as in the case with polychlorobiphenylols (OH-PCBs); or of natural origin. The present study was aimed to identify hitherto unknown PHCs in human plasma with chemical structures that are consistent to PHCs known to possess endocrine-disrupting activity. For this purpose, samples of blood plasma from 10 randomly selected male blood donors from Sweden were pooled and analyzed by GC/ECD and GC/MS. Brominated, bromochlorinated, and chlorinated methyl derivatives of phenols and OH-PCBs were synthesized to be used as authentic reference standards. More than 100 PHCs were indicated in the plasma, and among those a total of 9 monocyclic brominated or chlorinated phenol-, guaiacol-, and/or catechol-type compounds were identified as their methylated derivatives. The two major compounds were 2,4,6-tribromophenol and pentachlorophenol. Thirty-eight OH-PCB congeners were structurally identified on two GC columns of different polarity. The origin of the OH-PCB metabolites in the context of their parent PCB congeners are suggested. Other PHCs identified in the male plasma were Triclosan (5-chloro-2-[2,4-dichlorophenoxy] phenol), a common bactericide; 4-hydroxy-heptachlorostyrene, a metabolite of octachlorostyrene; and 3,5-dibromo-2-(2,4-dibromophenoxy)phenol, a natural compound and a potential metabolite of polybrominated diphenyl ethers.

Halogenation using quaternary ammonium polyhalides. XX. Bromination of phenols with polymer-bound benzyltrimethylammonium tribromide

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