2-bromophenol
phenol, 2-bromo-
Identification
| Name | 2-bromophenol |
| IUPAC | 2-bromophenol |
| CAS Number | 95-56-7 |
| EINECS | 202-432-7 |
| FDA UNII | A0UB206YF0 |
| Molecular Formula | C6 H5 Br O |
| Molecular Weight | 173.00905000 |
| MDL Number | MFCD00002146 |
| Nikkaji Number | J3.565C |
| Beilstein | 1905115 |
| XlogP3 | 2.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.63300 to 1.64500 @ 20.00 °C. |
| Pounds per Gallon - (est). | 13.604 to 13.704 |
| Refractive Index | 1.58400 to 1.59200 @ 20.00 °C. |
| Flash Point | 108.00 °F. TCC ( 42.22 °C. ) |
| Soluble in | water, 2227 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 2-bromophenol usage levels up to | not for fragrance use. |
| Recommendation for 2-bromophenol flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
o-
bromophenol
phenol, 2-bromo-
PubMed:
Theoretical study on the formation mechanism of pre-intermediates for PXDD/Fs from 2-Bromophenol and 2-Chlorophenol precursors via radical/molecule reactions.
PubMed:
Gas Purge Microextraction Coupled with Stable Isotope Labeling-Liquid Chromatography/Mass Spectrometry for the Analysis of Bromophenols in Aquatic Products.
PubMed:
Simultaneous determination of haloanisoles and halophenols in water using in situ acylation combined with solid-phase microextraction with gas chromatography and mass spectrometry.
PubMed:
The microbial degradation of 2,4,6-tribromophenol (TBP) in water/sediments interface: Investigating bioaugmentation using Bacillus sp. GZT.
PubMed:
Development of a Rapid Microbore Metabolic Profiling Ultraperformance Liquid Chromatography-Mass Spectrometry Approach for High-Throughput Phenotyping Studies.
PubMed:
Determination of urinary bromophenols (BrPs) as potential biomarkers for human exposure to polybrominated diphenyl ethers (PBDEs) using gas chromatography-tandem mass spectrometry (GC-MS/MS).
PubMed:
A New Reaction Pathway for Bromite to Bromate in the Ozonation of Bromide.
PubMed:
Antioxidant and acetylcholinesterase inhibition properties of novel bromophenol derivatives.
PubMed:
Sorption of halogenated phenols and pharmaceuticals to biochar: affecting factors and mechanisms.
PubMed:
Photochemical transformation of tetrabromobisphenol A under simulated sunlight irradiation: Kinetics, mechanism and influencing factors.
PubMed:
Simultaneous determination of brominated phenols in soils.
PubMed:
Regioselective synthesis of 2,3-dihydrobenzodioxepinones from epoxides and 2-bromophenols via palladium-catalyzed carbonylation.
PubMed:
Diindole-annulated naphthalene diimides: synthesis and optical and electronic properties of syn- and anti-isomers.
PubMed:
Bromine and carbon isotope effects during photolysis of brominated phenols.
PubMed:
In search of catalytic antioxidants--(alkyltelluro)phenols, (alkyltelluro)resorcinols, and bis(alkyltelluro)phenols.
PubMed:
New halogenated disinfection byproducts in swimming pool water and their permeability across skin.
PubMed:
Study of the photodegradation of 2-bromophenol under UV and sunlight by spectroscopic, chromatographic and chemometric techniques.
PubMed:
Suppressing effect of calcium-based waste on control of bromine flux during the pyrolysis of printed circuit boards.
PubMed:
Mechanism and direct kinetics study on the homogeneous gas-phase formation of PBDD/Fs from 2-BP, 2,4-DBP, and 2,4,6-TBP as precursors.
PubMed:
Simultaneous quantification of multiple classes of phenolic compounds in blood plasma by liquid chromatography-electrospray tandem mass spectrometry.
PubMed:
Distribution and formation of chlorophenols and bromophenols in marine and riverine environments.
PubMed:
Desulfoluna spongiiphila sp. nov., a dehalogenating bacterium in the Desulfobacteraceae from the marine sponge Aplysina aerophoba.
PubMed:
Biodegradation of brominated aromatics by cultures and laccase of Trametes versicolor.
PubMed:
Degradation of phenol via phenylphosphate and carboxylation to 4-hydroxybenzoate by a newly isolated strain of the sulfate-reducing bacterium Desulfobacterium anilini.
PubMed:
Acute toxicity of 353-nonylphenol and its metabolites for zebrafish embryos.
PubMed:
Synthesis of polybrominated diphenyl ethers via symmetrical tetra- and hexabrominated diphenyliodonium salts.
PubMed:
Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions.
PubMed:
One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols.
PubMed:
Improved approach for analyzing bromophenols in seafood using stable isotope dilution analysis in combination with SPME.
PubMed:
Understanding medicinal taste and odour formation in drinking waters.
PubMed:
Removal of bromophenols from water using industrial wastes as low cost adsorbents.
PubMed:
Molecular structures and properties of the complete series of bromophenols: Density functional theory calculations.
PubMed:
Formation of bromochlorodibenzo-p-dioxins and dibenzofurans from the high-temperature oxidation of a mixture of 2-chlorophenol and 2-bromophenol.
PubMed:
Surface-mediated formation of PBDD/Fs from the high-temperature oxidation of 2-bromophenol on a CuO/silica surface.
PubMed:
Formation of bromochlorodibenzo-p-dioxins and furans from the high-temperature pyrolysis of a 2-chlorophenol/2-bromophenol mixture.
PubMed:
Bromophenols, both present in marine organisms and in industrial flame retardants, disturb cellular Ca2+ signaling in neuroendocrine cells (PC12).
PubMed:
Surface-mediated formation of polybrominated dibenzo-p-dioxins and dibenzofurans from the high-temperature pyrolysis of 2-bromophenol on a CuO/silica surface.
PubMed:
Kinetics and mechanisms of formation of bromophenols during drinking water chlorination: assessment of taste and odor development.
PubMed:
Mechanisms of dioxin formation from the high-temperature oxidation of 2-bromophenol.
PubMed:
Enhancement of bromophenol levels in aquacultured silver seabream (Sparus sarba).
PubMed:
cDNA cloning, functional expression, and characterization of chicken sulfotransferases belonging to the SULT1B and SULT1C families.
PubMed:
Detection and characterization of a dehalogenating microorganism by terminal restriction fragment length polymorphism fingerprinting of 16S rRNA in a sulfidogenic, 2-bromophenol-utilizing enrichment.
PubMed:
Mechanisms of dioxin formation from the high-temperature pyrolysis of 2-bromophenol.
PubMed:
Seasonal distribution of bromophenols in selected Hong Kong seafood.
PubMed:
Photochemical transformations of tetrabromobisphenol A and related phenols in water.
PubMed:
Decomposition of 2-bromophenol in NaOH solution at high temperature.
PubMed:
Reductive dehalogenation of brominated phenolic compounds by microorganisms associated with the marine sponge Aplysina aerophoba.
PubMed:
Seasonal variations of bromophenols in brown algae (Padina arborescens, Sargassum siliquastrum, and Lobophora variegata) collected in Hong Kong.
PubMed:
Induction characteristics of reductive dehalogenation in the ortho-halophenol-respiring bacterium, Anaeromyxobacter dehalogenans.
PubMed:
Detection by PCR of reductive dehalogenase motifs in a sulfidogenic 2-bromophenol-degrading consortium enriched from estuarine sediment.
PubMed:
Acute and subacute nephrotoxicity of 2-bromophenol in rats.
PubMed:
Anaerobic biotransformation of tetrabromobisphenol A, tetrachlorobisphenol A, and bisphenol A in estuarine sediments.
PubMed:
Nickel-catalyzed cross-coupling of bromophenols with Grignard reagents in the solid phase synthesis.
PubMed:
Characterization and description of Anaeromyxobacter dehalogenans gen. nov., sp. nov., an aryl-halorespiring facultative anaerobic myxobacterium.
PubMed:
Anaerobic reductive dechlorination of chlorinated dioxins in estuarine sediments.
PubMed:
[Growth of Rhodococcus opacus on mixtures of monohalogenated benzenes and phenols].
PubMed:
Brominated anisoles and cresols in the red alga Polysiphonia sphaerocarpa.
PubMed:
Distribution of bromophenols in species of marine polychaetes and bryozoans from eastern Australia and the role of such animals in the flavor of edible ocean fish and prawns (shrimp).
PubMed:
Dehalogenation and biodegradation of brominated phenols and benzoic acids under iron-reducing, sulfidogenic, and methanogenic conditions.
PubMed:
Investigations on acute hepato- and nephrotoxicity of pentabromophenol.
PubMed:
Substrate, substrate analogue, and inhibitor interactions with the ferrous active site of catechol 2,3-dioxygenase monitored through XAS studies.
PubMed:
Potential for carboxylation-dehydroxylation of phenolic compounds by a methanogenic consortium.
PubMed:
Pathways of formation of 2-, 3- and 4-bromophenol from bromobenzene. Proposed mechanism for C-S lyase reactions of cysteine conjugates.
PubMed:
Dihydroxylated mercapturic acid metabolites of bromobenzene.
PubMed:
Early mitochondrial disfunction in bromobenzene treated mice: a possible factor of liver injury.
PubMed:
Effect of bromobenzene and O-bromophenol on kidney and liver of English sole (Parophrys vetulus).
PubMed:
Bromobenzene metabolism in the rat and guinea pig.
PubMed:
Cellular toxicity of bromobenzene and bromobenzene metabolites to rabbit proximal tubules: the role and mechanism of 2-bromohydroquinone.
PubMed:
Influence of mercuric chloride on the metabolism and hepatotoxicity of bromobenzene in rats.
PubMed:
Inhibition of respiration in rabbit proximal tubules by bromophenols and 2-bromohydroquinone.
PubMed:
Glutathione conjugates of 2-bromohydroquinone are nephrotoxic.
PubMed:
Bromobenzene metabolism in isolated rat hepatocytes. 18O2 incorporation studies.
PubMed:
Identification of 2-bromohydroquinone as a metabolite of bromobenzene and o-bromophenol: implications for bromobenzene-induced nephrotoxicity.
PubMed:
Nephrotoxicity of phenolic bromobenzene metabolites in the mouse.
PubMed:
The role of ortho-bromophenol in the nephrotoxicity of bromobenzene in rats.
PubMed:
The mechanism of formation of o-bromophenol from bromobenzene.
PubMed:
Hepatic bromobenzene epoxidation and binding: prevention by ascorbyl palmitate.
PubMed:
Bromobenzene metabolism in the rabbit: specific forms of cytochrome P-450 involved in 2,3- and 3,4-epoxidation.