2,4-Dibromophenol

log Kow = 3.22

3.22

3.48

Slightly soluble in carbon tetrachloride; very soluble in ethanol, ether, benzene

Very soluble in carbon disulfide

In water, 1.9X10+3 mg/L

1.9 mg/mL at 15 °C

38 °C

40 °C

Danger

H300 (92%): Fatal if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

Chemical: Phenol, 2,4-dibromo-

Hazard Traits - Hazard Trait Undefined

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Phenol, 2,4-dibromo-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 10/29/90; Reporting date: 12/27/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Dibromophenol is included on this list. Effective date 10/29/90; Sunset date: 12/19/95.

Acute Tox. 2 (92%)

Acute toxicity (Oral) - Category 2

Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.

Suitable: Water spray. Carbon dioxide, dry chemical powder, or appropriate foam.

Sweep up, place in a bag and hold for waste disposal. Avoid raising dust.

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. 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.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

Do not breathe dust. Do not get in eyes, on skin, on clothing. Avoid prolonged or repeated exposure.

For more Preventive Measures (Complete) data for 2,4-DIBROMOPHENOL (8 total), please visit the HSDB record page.

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

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 particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a log Kow of 3.22(2) and a regression-derived equation(3), indicates that 2,4-dibromophenol is expected to have low mobility in soil(SRC). The pKa of 2,4-dibromophenol is 7.79(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). Volatilization of 2,4-dibromophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 2,4-dibromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-3 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 1,300(SRC), determined from a log Kow of 3.22(2) and a regression-derived equation(3), indicates that 2,4-dibromophenol 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 8.9X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF of 16(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD 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), 2,4-dibromophenol, which has an estimated vapor pressure of 1.3X10-3 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 2,4-dibromophenol 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 5.6 days(SRC), calculated from its rate constant of 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,4-dibromophenol 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).

/AQUATIC SPECIES/ Bromophenols are present in polychaetes as well as in algae in marine environments including the North Sea. They are thought to cause the typical sea-like taste and flavor. The ecological function of brominated phenols is not clear yet, but they may play a role in chemical defense and deterrence ... In this study 2-bromophenol (2-BP), 4-bromophenol (4-BP), 2,4-dibromophenol (2,4-DBP), 2,6-dibromophenol (2,6-DBP) and 2,4,6-tribromophenol (2,4,6-TBP), all of which are present in marine organisms, were tested. Especially 2,4-DBP and 2,4,6-TBP showed a significant effect on the Ca2+ homeostasis in endocrine cells (PC 12). The reduction of depolarization induced Ca2+ elevations by 2,4-DBP and 2,4,6-TBP and the increase of intracellular Ca2+ by both substances, partly released from intracellular stores, may suggest a link to the disrupting effect of endocrine systems by brominated phenols. 2,4-DBP was the most potent substance ... tested in respect to inhibition of voltage dependent Ca2+ currents as revealed in whole cell patch clamp experiments. Brominated phenols disturb cellular Ca2+ signaling with differential efficacy, depending on the number and position of bromine.

2,4-Dibromophenol was identified in automotive emissions in the range of 1 to 5 ug/cu m(1). Fire residues sampled from private residences following accidental fires contained 2,4-dibromophenol, though the concentrations were reported as the sum of the various brominated flame retardants(2).

The Koc of 2,4-dibromophenol is estimated as 1,300(SRC), using a log Kow of 3.22(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-dibromophenol is expected to have low mobility in soil. The pKa of 2,4-dibromophenol is 7.79(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).

Study demonstrates the wide occurrence of bromophenols in marine algae and provides a possible source of such compounds in fish that feed predominantly on ocean plants. /Bromophenols/

Marine algae and bryozoa from the Gutters region of Exmouth Gulf, Western Australia are possible sources of bromophenols, including 2,4-dibromophenol, in the prawn, Metapenaeus endeavouri(1).

Endeavour prawns from Exmouth Gulf, Shark Bay, and Groote Elylandt, Australia, contained 2,4-dibromophenol at concentrations of 58 to 200, 160, and 31 ug/kg, respectively(1). Ten different species of fish, collected in August 1992 from the eastern coast of Australia, contained 2,4-dibromophenol at concentrations of <0.05 to 2.0 ng/g for the carcass and <0.05 to 150 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 1.2 ng/g, <0.01 to 23 ng/g, <0.01 to 2.0 ng/g, and 0.2 to 0.5 ng/g, respectively, while concentrations in the gut ranged from <0.01 to 3.3 ng/g, <0.01 to 320 ng/g, 0.1 to 150 ng/g, and 2.5 to 26 ng/g, respectively(3). Thirty samples of 9 species of prawns, collected from the eastern coast of Australia from 1993 to 1996, contained 2,4-dibromophenol at concentrations of 0.20 to 1100 ng/g(4). 2,4-Dibromophenol concentrations in cultivated prawns ranged from <0.01 to 0.59 ng/g(4). 2,4-Dibromophenol 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 0.727 to 9.47 ng/g and 0 to 5.36 ng/g, respectively; in the gut, concentrations ranged from 3.41 to 97.1 ng/g and 4.63 to 31.4 ng/g, respectively. In the mullusks, including clams (Tapes philippinarum) and oysters (Ostrea rivularis), seasonal concentrations ranged from 2.54 to 195 ng/g and 9.80 to 52.9 ng/g, respectively. For crustaceans, seasonal concentrations in the cephalothorax and tail of the shrimp (Penaeus japonicus) ranged from 1.78 to 10.4 ng/g and 0 to 6.78 ng/g, respectively; in crab (Charybdis feriatus), concentrations ranged from 27.6 to 214 ng/g(5).

AEROBIC: 2,4-Dibromophenol, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). An 81% ring degradation was reported for 2,4-dibromophenol, at 100 ppm, over a 4-day period using aerated soil sludge inoculum(2). 2,4-Dibromophenol, present at 251 and 251000 ppm, reached 550 and 0% 14-CO2 evolution after 5 days in a marine water sediment(3). 2,4-Dibromophenol was not degraded over 14 days in a marine water/sediment sample(3). Little activity was observed when 2,4-dibromophenol was tested in a Warburg respirometer using a mixed culture of soil, compost, or mud from a catalytic cracking plant waste lagoon where Pseudomonads predominated(4).

PURE CULTURE: Phenol-grown Rhodotorula glutinis, isolated from Rothamsted soil, consumed oxygen in the presence of 2,4-dibromophenol(1). O-methylation of 2,4-dibromophenol by whole cells of bacteria strains 1395 (Gram +) and 1678 (Gram -)occurred at a rate of 2.2X10+11 and 1.4X10+11 ug/hr/(number of cells per mL), respectively(2). 2,4-Dibromophenol, present at 0.1 mM, was dehalogenated by Pseudomonas cepacia AC1100. Measured by halogen release and HPLC methodology, the compound was found to degrade by 60% and 85%, respectively(3). 2,4-Dibromophenol was degraded by resting cells of Streptomyces rochei 303, isolated from soil; in 24 hours the compound degraded by >90% at 10 ppm, >95% at 20 ppm, >98% at 50 ppm, and >99% at 100 ppm(4).

ANAEROBIC: 2,4-Dibromophenol was degraded in an anaerobic sediment-water system; the half-life for this reaction was determined to be 5 days(1). A 1 mM solution of 2,4-dibromophenol was dehalogenated within 48 to 72 hours following a lag time of 10 to 20 hrs, when incubated in marine sediment enrichments(2).

SEDIMENT: Surficial sediments from the Rhone estuary, collected in 1987/1988, contained 2,4-dibromophenol at concentrations of 7 to 5,848 ng/g, dry weight basis, from 5 sampling sites(1). Upper river and marine sediment layers in Osaka Prefecture, Japan, collected in 1981 through 1983 at 12 different locations, contained 2,4-dibromophenol at concentrations <0.2 ppb (dry weight basis)(2).

A BCF of 16 for 2,4-dibromophenol was deteremined using in carp (Cyprinus carpio) which were exposed over a 28-day period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 10/29/90; Reporting date: 12/27/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Dibromophenol is included on this list. Effective date 10/29/90; Sunset date: 12/19/95.

The metabolism and disposition of (14)C-labelled 2,2',4,4'-tetrabromodiphenyl ether (BDE47) were investigated in F344 rats and B6C3F1 mice. Approximately 75-85% of 1 umol BDE47 per kg was absorbed following oral administration to either rats or mice. Sex and species differences were observed in tissue distribution and excretion of BDE47-derived radioactivity. Absorption and distribution of (14)C to major tissues were dose-proportional in male rats from 0.1 to 1,000 umol per kg. BDE47-derived radioactivity increased in all rat and mouse tissues examined following repeated daily doses of 1 umol per kg. Accumulation of (14)C in tissues of mice was less than in corresponding rat tissues. Glutathione conjugates of BDE47 were excreted in rat bile. A glucuronide and a sulfate conjugate of 2,4-dibromophenol were detected in the urine of BDE47-treated rats. BDE47 appears to induce its own metabolism. Increased formation of reactive metabolites over time may correlate with toxicological effects in BDE47-treated rodents.