2-Bromophenol

log Kow = 2.35

2.35

2.35

5.6 °C

5.6 °C

Warning

H226 (88.1%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 59 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Phenol, 2-bromo-

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Phenol, 2-bromo-: Does not have an individual approval but may be used under an appropriate group standard

Nephrotoxicity observed in rats at high doses; [INCHEM CICADS] Causes other changes in urine composition, other changes of the kidney, and proteinuria in acute oral studies of rats; Causes tremor, convulsions, and muscle weakness in subcutaneous lethal-dose studies of guinea pigs; Causes delayed allergic hypersensitivity (multiple organ involvement) in 140-day intermittent inhalation studies of mice; [RTECS] A skin and strong eye irritant; Harmful by ingestion and skin absorption; [Alfa Aesar MSDS] See 2-Chlorophenol.

Materials to Avoid: Acid chlorides, Acid anhydrides, Oxidizing agents.

Combustible (USA) Flammable (EU)

Flam. Liq. 3 (88.1%)

Acute Tox. 4 (100%)

Flammable liquids - Category 3

Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. Specific Hazard(s): Emits toxic fumes under fire conditions. Combustible liquid.

Suitable: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.

Cover with dry lime or soda ash, pick up, keep in a closed container, and hold for waste disposal.

A comparative study of the adsorbents prepared from several industrial wastes for the removal of 2-bromophenol, 4-bromophenol and 2,4-dibromophenol has been carried out. The results show that maximum adsorption on carbonaceous adsorbent prepared from fertilizer industry waste has been found to be 40.7, 170.4 and 190.2 mg/g for 4-bromophenol 2-bromophenol and 2,4-dibromophenol, respectively. As compared to carbonaceous adsorbent, the other three adsorbents (viz., blast furnace sludge, dust, and slag) adsorb bromophenols to a much smaller extent. ... To test the practical utility of this adsorbent, column operations were also carried out. The results were found satisfactory in removing bromophenols by column operations. Therefore, the ... investigations recommend the use of carbon slurry waste as inexpensive adsorbent for small scale industries of developing/poor countries where disposal of solid waste of various industries and proper treatment of polluted wastewater is a serious problem.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Contact a licensed professional waste disposal service to dispose of this material. This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Do not breathe vapor. Avoid contact with eyes, skin, and clothing. Avoid prolonged or repeated exposure.

Wear respirator, chemical safety goggles, rubber boots, and heavy rubber gloves.

In case of contact, immediately flush eyes with copious amounts of water for at least 15 minutes.

For more Preventive Measures (Complete) data for 2-BROMOPHENOL (6 total), please visit the HSDB record page.

Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Hand: Compatible chemical-resistant gloves. Eye: Chemical safety goggles.

ENGINEERING CONTROLS: Use only in a chemical fume hood. Safety shower and eye bath.

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 60000 ug/L for 48 hr; Effect: decreased population biomass /formulated product/

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 110000 ug/L for 48 hr; Effect: population changes, general /formulated product/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, renewal, 25 °C, pH >7; Concentration: 13000 ug/L for 24 hr; Effect: behavior, equilibrium /formulated product/

EC50; Species: Daphnia magna (Water flea, age < or =24 hr); Conditions: freshwater, static, 25 °C, pH >7.0, dissolved oxygen > or =58%; Concentration: 13000 ug/L for 24 hr; Effect: intoxication, immobilization /formulated product/

For more Ecotoxicity Values (Complete) data for 2-BROMOPHENOL (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 450(SRC), determined from a log Kow of 2.35(2) and a regression-derived equation(3), indicates that 2-bromophenol is expected to have moderate mobility in soil(SRC). The pKa of 2-bromophenol is 8.45(4), indicating that this compound will partially exist in the anion in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 2-bormophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 2-Bromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-2 mm Hg(SRC), determined from a fragment constant method(7). A theoretical BOD of 0% using activated sludge in the Japanese MITI test(8) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 450(SRC), determined from a log Kow of 2.35(2) indicates that 2-bromophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an experimentally derived BCF of 20-33(6) suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). A theoretical BOD of 0% using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-bromophenol, which has an estimated vapor pressure of 3.7X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-bromophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.7 days(SRC), calculated from its rate constant of 9.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Bromophenol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: 2-Bromophenol is used as a precursor to resorcinol. It is a yellow to red oily liquid with an unpleasant odor. It is slightly soluble in chloroform; soluble in ethanol, ether, alkali, and water. HUMAN EXPOSURE AND TOXICITY: It is harmful if swallowed.2-Bromophenol causes skin irritation. It may be harmful if absorbed through the skin. Causes eye irritation and is irritating to mucous membranes and the upper respiratory tract. Occupational exposure to this chemical may occur through inhalation, and dermal contact with these compounds at workplaces where these chemicals are produced or used. Monitoring data indicate that the general population may be exposed to bromophenols by inhalation, ingestion of food, and drinking water, and dermal contact. In an in vitro assay based on H295R human adrenocortical carcinoma cell line, which possesses most key genes or enzymes involved in steroidogenesis, of five bromophenols. Among the genes tested, 3betaHSD2 was the most markedly upregulated, with a range of magnitude from 1.6-20.0 fold. The results demonstrate that bromophenol bromobiphenyls and bromodibenzo-p-dioxin/furan are able to modulate steroidgenenic gene expression, which may lead to endocrine disruption. ANIMAL STUDIES: 2-Bromophenol administered ip caused a decrease in renal glutathione levels. In contrast, hepatic glutathione levels remained close to control values after chemical administration. Renal glutathione was far more susceptible to the initial rapid depleting effects of 2-bromophenol than was hepatic glutathione, the dose response curve for hepatic glutathione depletion being shifted to the right. 2-Bromophenol was found to be hepatotoxic in English sole, as indicated by the presence of hepatocellular coagulation necrosis and fatty change in the liver, altered glutathione and ascorbic acid levels in liver tissue, elevated serum aspartate aminotransferase and alkaline phosphatase activity and increased serum glucose and triglyceride levels. No evidence of nephrotoxicity was found in English sole exposed to either toxicant

/AQUATIC SPECIES/ English sole (Parophrys vetulus) were injected intraperitoneally with a single dose of 9.8 mmol bromobenzene/kg of fish or 1.9 mmol o-bromophenol/kg of fish, both known renal toxicants in mammals. Kidney, liver, gill spleen, intestines, heart and blood samples were subsequently obtained up to 48 hr post-injection for determination of microscopic lesions, concentrations of selected tissue antioxidants (glutathione and ascorbic acid), and selected serum parameters. Bromobenzene and o-bromophenol were both found to be hepatotoxic in English sole, as indicated by the presence of hepatocellular coagulation necrosis and fatty change in the liver, altered glutathione and ascorbic acid levels in liver tissue, elevated serum aspartate aminotransferase and alkaline phosphatase activity and increased serum glucose and triglyceride levels. No evidence of nephrotoxicity was found in English sole exposed to either toxicant...

The raw flue gas from a Swedish hazardous waste incinerator, located at Norrtorp, and fed chlorinated (mainly solvents) and brominated waste (tetrabutylammonium bromide) contained 3-bromophenol at 24, 230, and 31 ng/cu m over three tests, respectively; bromides were present initially at 32, 1100, and 530 mg/cu m, respectively(1).

2-Bromophenol was identified in automotive emissions in the range of 1 to 5 ug/cu m(1). 2-Bromophenol was indentified in industrial wastewater samples from photographic industries at 24 ng/uL(2). The raw flue gas from a Swedish hazardous waste incinerator, located at Norrtorp, and fed chlorinated (mainly solvents) and brominated waste (tetrabutylammonium bromide) contained 2-bromophenol at 36, 110, and 16 ng/cu m over three tests, respectively; bromides were present initially at 32, 1100, and 530 mg/cu m, respectively(3).

The Koc of 2-bromophenol is estimated as 450(SRC), using a log Kow of 2.35(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-bromophenol is expected to have moderate mobility in soil. The pKa of 2-bromophenol is 8.45(4) indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

/SIGNS AND SYMPTOMS/ Causes skin irritation. May be harmful if absorbed through the skin. Causes eye irritation. Inhalation: May be harmful if inhaled. Material is irritating to mucous membranes and upper respiratory tract. Harmful if swallowed. TARGET ORGAN(S) OR SYSTEM(S) Eyes. Depending on the intensity and duration of exposure, effects may vary from mild irritation to severe destruction of tissue.

Endeavour prawns from Exmouth Gulf, Shark Bay, and Groote Elylandt, Australia, contained 2-bromophenol at concentrations of 9.6 to 53, 2.7, and 1.0 ug/kg, respectively(1). Ten different species of fish, collected in August 1992 from the eastern coast of Australia, contained 2-bromophenol at concentrations of <0.05 to 0.1 ng/g for the carcass and <0.05 to 5.2 ng/g for the whole gut (analysis of single fish from each species)(2). Ocean fish were separated by species into pelagic carnivores, benthic carnivores, diverse omnivores and restricted omnivores; concentrations in the flesh ranged from <0.01 to 0.1 ng/g, <0.01 to 5.2 ng/g, <0.01 to 0.4, and <0.01 to 0.1 ng/g, respectively, while concentrations in the gut ranged from <0.01 to 0.2 ng/g, <0.01 to 27 ng/g, <0.01 to 1.2 ng/g, and <0.01 to 0.7 ng/g, respectively(3). Thirty samples of 9 species of prawns, collected from the eastern coast of Australia from 1993 to 1996, contained 2-bromophenol at concentrations of <0.01 to 42 ng/g(4). 2-Bromophenol concentrations in cultivated prawns ranged from <0.01 to 0.02 ng/g in the head and <0.01 to 0.01 ng/g in the tail(4). 2-Bromophenol was detected in marine fish, mollusks, and crustaceans obtained from a seafood shop in Hong Kong. Seasonal concentrations in the flesh of rabbitfish (Siganus canaliculatus) and brown-spotted grouper (Epinepheus areolatus) ranged from 0 to 10.7 ng/g and 0 to 4.18 ng/g, respectively; in the gut, concentrations ranged from 0 to 30.8 ng/g and 0 to 17.5 ng/g, respectively. In the mullusks, including clams (Tapes philippinarum) and oysters (Ostrea rivularis), seasonal concentrations ranged from 0.170 to 17.2 ng/g and 1.85 to 6.10 ng/g, respectively. For crustaceans, seasonal concentrations in the cephalothorax and tail of the shrimp (Penaeus japonicus) ranged from 1.27 to 7.72 ng/g and 0.421 to 5.87 ng/g, respectively; in crab (Charybdis feriatus), concentrations ranged from 0.991 to 34.4 ng/g(5).

2-Bromohydroquinone was identified as a metabolite of both bromobenzene and o-bromophenol in the rat in vivo and in vitro. Identification was based on high-pressure liquid chromatography and gas chromatography-mass spectrometry. Formation of 2-bromohydroquinone by rat liver microsomes from both bromobenzene and o-bromophenol was increased by treatment of rats with either phenobarbital or 3-methylcholanthrene. Covalent binding of o-bromophenol to rat liver microsomes was inhibited by glutathione and ascorbate but not by superoxide dismutase or catalase. Liver microsomes converted o-bromophenol to 2-bromohydroquinone and covalently bound material, whereas kidney and lung microsomes metabolized o-bromophenol less rapidly.

p-Bromophenol and o-bromophenol were the major urinary phenolic bromobenzene metabolites although m-bromophenol and 4-bromocatechol were also excreted in detectable quantities. With the exception of o-bromophenol, urinary metabolites were excreted primarily as conjugates.

Incubation of either o-bromophenol or 2-bromohydroquinone with rat liver microsomes and 0.25 mM 35S-glutathione (GSH) gave rise to several isomeric 35S-GSH conjugates. A mixture of these isomeric GSH conjugates was prepared chemically and two were purified by HPLC; 1H-NMR spectroscopy revealed that one was 2-bromo-3-(glutathion-S-yl)hydroquinone and the other was a disubstituted GSH conjugate which could be either 2-bromo-3,5-(diglutathion-S-yl)hydroquinone or 2-bromo-3,6-(diglutathion-S-yl)hydroquinone. Injection of the disubstituted GSH conjugate intravenously to rats caused substantial elevations in blood urea nitrogen levels. Treatment of rats with AT-125 (Acivicin; NSC 163501; 10 mg/kg ip) caused a substantial inhibition of kidney gamma-glutamyl transpeptidase activity and decreased 2-bromohydroquinone-mediated elevations in blood urea nitrogen. These findings are consistent with the view that the kidney necrosis observed after administration of either bromobenzene (1), o-bromophenol (2), or 2-bromohydroquinone (3) might be due in part to 2-bromohydroquinone GSH conjugates formed in the liver and subsequently transported to the kidney and converted to ultimate nephrotoxic metabolite(s).

4-Bromocatechol and the /o-, m- and p-/ bromophenol isomers were nephrotoxicants (measured as increased blood urea nitrogen and decreased accumulation of organic anions by renal cortical slices) but not hepatotoxicants (measured as serum glutamic pyruvate transaminase) in vivo at 0.56 mmol/kg (iv).

2-bromophenol (2-(BP)), 3-BP, and 4-BP can all be formed during the metabolism of bromobenzene in both rats and guinea-pigs. 2-BP is formed predominantly by spontaneous isomerization of the 2,3-oxide. 3-BP is formed via the sulfur-series pathway to phenols, which involves the enterohepatic circulation, with the key intermediate being S-(2-hydroxy-4-bromocyclohexa-3,5-dienyl)-L-cysteine, derived from the 4-S-glutathione conjugate of the 3,4-oxide. 4-BP is formed by the sulfur-series route from the S-(2-hydroxy-5-bromocyclohexa-3,5-dienyl)-L-cysteine. Additional suggested in vivo routes to 3- and 4-BP involve dehydration/aromatization of the 3,4-dihydro-3,4-diol, possibly by way of conjugates.

Used as a precursor to resorcinol; [HSDB]

Precursor to resorcinol

Phenol, 2-bromo-: ACTIVE

Phenol, bromo-: INACTIVE