2,4,6-TRIBROMOPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H3Br3O
Molecular Weight	330.799
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(Br)C=C(Br)C=C1Br

InChI

InChIKey=BSWWXRFVMJHFBN-UHFFFAOYSA-N

InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

HIDE SMILES / InChI

Molecular Formula	C6H3Br3O
Molecular Weight	330.799
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.deroyal.com/filedisplay.aspx?id=69
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27613672

The substance 2,4,6-Tribromophenol (TBP) is used as a flame retardant in electronic and electric devices, and is a replacement for pentachlorophenol in wood preservation. TBP is a contaminant in different environmental matrices, at levels where treatment is required. 2,4,6-Tribromophenol (bismuth tribromophenate) has been used individually and in combination to control microbial growth in burn wounds and on healing meshed skin graft.

Approval Year

Targets

Primary Target	Pharmacology	Potency
α-Glucosidase, Saccharomyces cerevisiae 2 Target ID: α-Glucosidase, Saccharomyces cerevisiae Sources: https://www.ncbi.nlm.nih.gov/pubmed/25962377	Inhibitor 8504	24.0 µM [IC50]
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601080	Antagonist 2849	8.3 µM [IC50]
Transthyretin 6 Target ID: CHEMBL3194 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601080	Binding Agent 1076	0.0048 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Burn 40 Sources: http://www.deroyal.com/filedisplay.aspx?id=69	Primary		Approved 8583	Xeroform Petrolatum Wound Dressing Approved Use Minimally draining wounds, Surgical incisions, Lacerations, Donor sites, Burns
Lacerations 3 Sources: http://www.deroyal.com/filedisplay.aspx?id=69	Primary		Approved 8583	Xeroform Petrolatum Wound Dressing Approved Use Surgical incisions • Donor sites • Skin grafts • First and second degree burns • Lacerations • Abrasions

Doses

Dose	Population	Adverse events
5 % single, topical Highest studied dose Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/6653119/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6653119/	Disc. AE: Contact dermatitis... AEs leading to discontinuation/dose reduction: Contact dermatitis Sources: https://pubmed.ncbi.nlm.nih.gov/6653119/

AEs

AE	Significance	Dose	Population
Contact dermatitis	Disc. AE	5 % single, topical Highest studied dose Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/6653119/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6653119/

PubMed

Title	Date	PubMed
Characterizing the peroxisome proliferator-activated receptor (PPARγ) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust.	2015-02	25314719
PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase.	2014-04-02	24699145
Optimisation of a dispersive liquid-liquid microextraction method for the simultaneous determination of halophenols and haloanisoles in wines.	2010-12-03	21035812
Neutral and phenolic brominated organic compounds of natural and anthropogenic origin in northeast Atlantic Greenland shark (Somniosus microcephalus).	2010-12	20891018
Oral exposure of adult zebrafish (Danio rerio) to 2,4,6-tribromophenol affects reproduction.	2010-10-01	20719397
Internal binding of halogenated phenols in dehaloperoxidase-hemoglobin inhibits peroxidase function.	2010-09-08	20816071
Biodegradation kinetics of selected brominated flame retardants in aerobic and anaerobic soil.	2010-06	20227803
Chronic exposure to environmental levels of tribromophenol impairs zebrafish reproduction.	2010-02-15	19931292
Gas chromatography coupled to electron capture negative ion mass spectrometry with nitrogen as the reagent gas--an alternative method for the determination of polybrominated compounds.	2009-12	19904736
Photochemical decomposition of dissolved hydroxylated polybrominated diphenyl ethers under various aqueous conditions.	2009-10	19726071
Tribromophenol and pentachlorophenol uptake from sawdust to horticultural products.	2009-10	19701836
Distribution and formation of chlorophenols and bromophenols in marine and riverine environments.	2009-10	19664797
Measuring Ca2+-signalling at fertilization in the sea urchin Psammechinus miliaris: alterations of this Ca2+-signal by copper and 2,4,6-tribromophenol.	2009-08	19460461
Biodegradation of brominated aromatics by cultures and laccase of Trametes versicolor.	2009-08	19443012
Bromophenol concentrations in fish from Salvador, BA, Brazil.	2009-06	19488620
Brominated flame retardants and other polyhalogenated compounds in indoor air and dust from two houses in Japan.	2009-06	19361833
Uptake and biotransformation of structurally diverse brominated flame retardants in zebrafish (Danio rerio) after dietary exposure.	2009-05	19049262
Different modes of binding of mono-, di-, and trihalogenated phenols to the hemoglobin dehaloperoxidase from Amphitrite ornata.	2009-03-17	19228049
Environmental impact of flame retardants (persistence and biodegradability).	2009-02	19440395
Metabolism of polybrominated diphenyl ethers (PBDEs) by human hepatocytes in vitro.	2009-02	19270788
Multifunctional in situ photopolymerized semi-interpenetrating network system is an effective donor site dressing: a cross comparison study in a swine model.	2009-01-10	19131760
Haloanisole and halophenol contamination in Spanish aged red wines.	2009-01	19680868
Determination of halophenolic wood preservant traces in milk using headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2008-12-26	19027907
Potent alpha-glucosidase inhibitors purified from the red alga Grateloupia elliptica.	2008-11	18951591
Contrasting the seasonal variability of halogenated natural products and anthropogenic hexachlorocyclohexanes in the southern Norwegian atmosphere.	2008-11	18330614
Desulfovibrio marinisediminis sp. nov., a novel sulfate-reducing bacterium isolated from coastal marine sediment via enrichment with Casamino acids.	2008-10	18842870
Improved approach for analyzing bromophenols in seafood using stable isotope dilution analysis in combination with SPME.	2008-09-24	18754626
Comparison of stir bar sorptive extraction and solid-phase microextraction to determine halophenols and haloanisoles by gas chromatography-ion trap tandem mass spectrometry.	2008-05-15	18585142
Biodegradation of 2,4,6-tribromophenol by Ochrobactrum sp. strain TB01.	2008-05	18460800
Determination of pentachlorophenol and tribromophenol in sawdust by ultrasound-assisted extraction and MEKC.	2008-04	18327848
Identification of brominated and chlorinated phenols as potential thyroid-disrupting compounds in indoor dusts.	2008-03-01	18441837
Effects of pH on the water solubility and 1-octanol-water partition coefficient of 2,4,6-tribromophenol.	2008-02	18246214
Immunochemical analysis of 2,4,6-tribromophenol for assessment of wood contamination.	2008-01-09	18069782
Adsorption characteristics of carbonaceous adsorbents for organic pollutants in a model incineration exhaust gas.	2008-01	17869323
A new highly specific and robust yeast androgen bioassay for the detection of agonists and antagonists.	2007-11	17849102
Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromodiphenyl ether mixture.	2007-07	17637922
Optimisation of a microwave-assisted extraction method for the simultaneous determination of haloanisoles and halophenols in cork stoppers.	2007-05-18	17386931
Effects of brominated flame retardants and brominated dioxins on steroidogenesis in H295R human adrenocortical carcinoma cell line.	2007-04	17447562
Optimisation of a headspace solid-phase microextraction with on-fiber derivatisation method for the direct determination of haloanisoles and halophenols in wine.	2007-03-02	17258751
Synthesis and characterization of 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) and structurally related compounds evidenced in seal blubber and brain.	2007-03-01	17396646
The pH dependence of the activity of dehaloperoxidase from Amphitrite ornata.	2007-01	17182294
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
The marine secondary metabolites 2,4-dibromophenol and 2,4,6-tribromophenol differentially modulate voltage dependent ion currents in neuroendocrine (PC12) cells.	2006-10-12	16911838
Development of a solid-phase microextraction method for the analysis of phenolic flame retardants in water samples.	2006-08-18	16600262
Proximal cavity, distal histidine, and substrate hydrogen-bonding mutations modulate the activity of Amphitrite ornata dehaloperoxidase.	2006-08-01	16866354
Reductive dehalogenation of tetrabromobisphenol-A by sediment from a contaminated ephemeral streambed and an enrichment culture.	2006-08	16497360
In vitro profiling of the endocrine-disrupting potency of brominated flame retardants.	2006-07	16601080
Formation of bromochlorodibenzo-p-dioxins and dibenzofurans from the high-temperature oxidation of a mixture of 2-chlorophenol and 2-bromophenol.	2006-05-01	16719108
Biodegradability of tetrabromobisphenol A and tribromophenol by activated sludge.	2006-05	16708282
Determination of simple bromophenols in marine fishes by reverse-phase high performance liquid chromatography (RP-HPLC).	2005-12-15	18970325

Patents

Sample Use Guides

In Vivo Use Guide

Xeroform Petrolatum Wound Dressing is a sterile, fine mesh gauze impregnated with a blend of 3% 2,4,6-TRIBROMOPHENOL (Bismuth Tribromophenate) and USP Petrolatum 1. Irrigate / Cleanse wound with sterile saline solution or sterile water. Gently dry surrounding skin. 2. Peel open pouch and remove Xeroform Petrolatum Wound Dressing from package. 3. Place dressing directly over wound. 4. Cover with appropriate cover / secondary dressing. 5. Change dressing per physician instructions. Recommended for daily dressing change to maintain a moist, non-adherent environment.

Route of Administration: Topical

In Vitro Use Guide

2,4,6-tribromophenol showed a dose-dependent effect on fertilization rates of P. miliaris and significantly inhibited fertilization at 1 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:00:07 GMT 2025` Edited by `admin` on `Mon Mar 31 19:00:07 GMT 2025`
Record UNII	YS6K3EU393
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BROMKAL PUR 3

Preferred Name

English

2,4,6-TRIBROMOPHENOL

Systematic Name

English

PHENOL, 2,4,6-TRIBROMO-

Systematic Name

English

2,4,6-TRIBROMOPHENOL [HSDB]

Common Name

English

FLAMMEX 3BP

Brand Name

English

TRIBROMOPHENOL, 2,4,6-

Systematic Name

English

NSC-2136

Code

English

BROMOL

Systematic Name

English

2,4,6-TRIBROMOPHENOL [MI]

Common Name

English

2,4,6-TRIBROMO-1-HYDROXYBENZENE

Systematic Name

English

Code System Code Type Description

PUBCHEM

1483