HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromophenol
P-BROMOPHENOL · Para Bromo Phenol · 4-Bromphenol · Phenol, 4-bromo- · NSC 4970 · p-Bromphenol · 4-BROMOPHENOL · BROMOPHENOL-4
Identifiers & Physical Properties
| CAS No. | 106-41-2 |
|---|---|
| Molecular formula | C6H5BrO |
| Average molar mass | 173.01 g/mol |
| Monoisotopic mass | 171.95237688 g/mol |
| SMILES | Oc1ccc(Br)cc1 |
| InChIKey | GZFGOTFRPZRKDS-UHFFFAOYSA-N |
| PubChem CID | 7808 |
| ChEMBL | CHEMBL57284 |
| ChEBI | CHEBI:47248 |
| EC No. | 203-394-4 |
| DTXSID | DTXSID3051543 |
Chemical & Physical Properties
| XLogP | 2.6 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 66.9 |
| Chemical classes | Other Classes -> Phenols |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pesticides | Biocide |
| LogP (partition coefficient) | log Kow = 2.592.74 |
| Density | 1.840 g/cu cm at 15 °CDensity: 1.5875 at 80 °C |
| Color/Form | Tetragonal bipyramidal crystals from chloroform or ether |
| Solubility | Freely soluble in alcohol, chloroform, ether, glacial acetic acidIn water, 1.4X10+4 mg/L at 25 °C14g/lIt is insoluble in water. It is soluble in 5%ethanol. |
| Boiling point | 238 °C235-236 °C (lit.) |
| Melting point | 66.4 °C61-64 °C (lit.) |
| Vapor pressure | 0.01 [mmHg]1.17X10-2 mm Hg at 25 °C |
| Henry's law constant | Henry's Law constant = 1.51X10-7 atm-cu m/mol at 25 °C6.7×101 mol/(m3Pa) at 25℃, Abraham et al. (1994) |
| Physical Description | Solid[Merck Index] Off-white crystalline powder with a phenolic odor[Alfa Aesar MSDS] |
| Refractive index | 1.5085 (estimate) |
| Flash point | 235-238°C |
| Storage conditions | room temp |
| Physical state | Crystalline Solid |
| pKa (acidity coefficient) | 9.37(at 25℃) |
| Color | Pinkish-brown |
| λmax | 282nm(EtOH)(lit.) |
| Merck | 14,1428 |
| BRN | 1680024 |
| InChI | 1S/C6H5BrO/c7-5-1-3-6(8)4-2-5/h1-4,8H |
| InChIKey | GZFGOTFRPZRKDS-UHFFFAOYSA-N |
| SMILES | Oc1ccc(Br)cc1 |
| CAS DataBase Reference | 106-41-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | LAO4J0183I |
| NIST Chemistry Reference | 4-Bromophenol(106-41-2) |
| EPA Substance Registry System | Phenol, 4-bromo- (106-41-2) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H361-H411 |
| GHS precautionary statements | P501-P273-P270-P202-P201-P264-P280-P302+P352-P391-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P405 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Safety statements (S) | 26-37/39-36 |
| UN transport number | 2811 |
| Water hazard class (WGK) | 2 |
| RTECS number | SJ7960000 |
| F | 8-10-23 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1(b)Acute Tox. 4 OralSkin Irrit. 2 |
| Packing group | III |
| Customs code | 29081000 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 106-41-2(Hazardous Substances Data) |
| Toxicity | mouse,LD50,intraperitoneal,411mg/kg (411mg/kg),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. |
Safety & Regulations
| GHS classification | WarningH302 (91.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 61 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]P273, P391, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: Phenol, 4-bromo-Phenol, 4-bromo-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | No nephrotoxicity observed in rats[INCHEM CICADS] A skin and strong eye irritantHarmful by skin absorptionToxic by ingestion[Alfa Aesar MSDS] See o-Bromophenol and 4-Chlorophenol. |
| Special Reports | WHOConcise International Chemical Assessment Document No 66, 2,4,6 Tribromophenol and other simple brominated phenols. Available at http://www.inchem.org/documents/cicads/cicads/cicad66.htm as of September 24, 2008. |
| Hazard Classes and Categories | Acute Tox. 4 (91.8%)Acute toxicity (Oral) - Category 4Hazardous to the aquatic environment (Acute) - Category 2 |
| Skin, Eye, and Respiratory Irritations | Causes respiratory tract irritation. Causes skin irritation.Causes eye irritation. |
| Firefighting Hazards | Hazardous decomposition products formed under fire conditions. - Hydrogen bromide gas |
| Fire fighting procedures | Wear self contained breathing apparatus for fire fighting if necessary.Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. |
| Cleanup methods | Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for 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. |
| Disposal methods | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. |
| Preventive Measures | 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: 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.Handle with gloves. Wear safety glasses for eye protection. Choose body protection according to the amount and concentration of the dangerous substance at the work place.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.For more Preventive Measures (Complete) data for 4-BROMOPHENOL (8 total), please visit the HSDB record page. |
| Personal Protective Equipment (PPE) | Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).ENGINEERING CONTROLS: Use only in a chemical fume hood. Safety shower and eye bath. |
| Ecotoxicity values | EC50Species: Daphnia magna (Water flea, age 12 hr)Conditions: freshwater, static, 18 °CConcentration: 5950 ug/L for 48 hrEffect: intoxication, immobilization /formulated product/ |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 610(SRC), determined from a log Kow of 2.59(2) and a regression-derived equation(3), indicates that 4-bromophenol is expected to have low mobility in soil(SRC). The pKa of 4-bromophenol is 9.17(4), indicating that this compound will exist partially 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 4-bromophenol from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.51X10-7 atm-cu m/mole(6). 4-Bromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-2 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 fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 610(SRC), determined from a log Kow of 2.59(2) and a regression-derived equation(3), indicates that 4-bromophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.5X10-7 atm-cu m/mole(4). According to a classification scheme(5), an experimental BCF of 8.0 to 12(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD of 0% using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-bromophenol, which has an estimated vapor pressure of 1.17X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-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). 4-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). |
| Plant Concentrations | Concentrations of 4-bromophenol were measured in brown algae (0 to 13 ug/kg wet weight), red algae (0 to 0.84 ug/kg), bryozoa (2.3 and 18 ug/kg) and a hydroid (4.9 ug/kg) collected from Exmouth Gulf, Australia, in October 1990(1). |
| Animal Concentrations | Concentrations of 4-bromophenol were measured in sponges (0.42 to 62 ug/kg) collected from Exmouth Gulf, Australia, in October 1990(1). |
| Effluent Concentrations | 4-Bromophenol was identified in automotive emissions in the range of 0.1 to 0.3 ug/cu m(1). 4-Bromophenol was identified in industrial wastewater samples from photographic industries at 187 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 3-/4-bromophenol at 24, 230, and 31 ng/cu m over three tests, respectivelybromides were present initially at 32, 1100, and 530 mg/cu m, respectively(3). |
| Soil Adsorption/Mobility | The Koc of 4-bromophenol is estimated as 610(SRC), using a log Kow of 2.59(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-bromophenol is expected to have low mobility in soil. The pKa of 4-bromophenol is 9.17(4), indicating that this compound will exist partially 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). |
| Natural Pollution Sources | Studies indicate that there is a wide occurrence of bromophenols, including 4-bromophenol, in marine algae which provides a possible source of such compounds in fish that feed predominantly on ocean plants(1). |
| Human Toxicity Excerpts | /ENDOCRINE MODULATION/ ... The estrogen-like activity of phenol, 4-bromophenol (4-BP), 2,4-dibromophenol (2,4-DBP), 2,4,6-tribromophenol (2,4,6-TBP) and 4-tert-butylphenol (tert-BP) /was characterized/ using the estrogen-dependent human breast cancer cell line MCF-7. 4-BP, 2,4-DBP and 4-tert-BP all bind to the estrogen receptor (ER) with approximately 10,000-fold less affinity than 17 beta-estradiol (17 beta-E). 2,4,6-TBP was only able to displace 43% of radiolabelled estrogen when tested at concentrations up to 1 uM, whereas phenol had no affinity for the ER. 4-tert-BP stimulated cell growth and induced estrogen-regulated proteins such as the progesterone receptor (PgR) and pS2. The brominated phenols, however, although binding to the ER, did not stimulate cell growth or increase the levels of the PgR or pS2, or reduce the level of 17 beta-E induced pS2. On the contrary, 4-BP, 2,4-DBP and partly 4-tert-BP reduced 17 beta-E-stimulated cell growth apparently by an ER independent mechanism./ALTERNATIVE and IN VITRO TESTS/ /The/ study assessed the potential effects of nineteen polybrominated diphenyl ethers (BDEs), five hydroxylated BDEs (OH-BDEs), one methoxylated BDE (CH(3)O-BDE), tetrabromobisphenol-A (TBBPA), its dibromopropane ether derivative (TBBPA-DBPE), and the brominated phenols/anisols 2,4,6-tribromophenol (TBP), 4-bromophenol (4BP) and 2,4,6-tribromoanisole (TBA) on the catalytic activity of the steroidogenic enzyme aromatase (CYP19) in H295R human adrenocortical carcinoma cells. Effects were studied in the concentration range from 0.5 to 7.5 uMexposures were for 24 hr. Both 6-OH-BDE47 and 6-OH-BDE99 showed an inhibitory effect on aromatase activity at concentrations >2.5 uM and >5 uM, respectively. However, 6-OH-BDE47 also caused a statistically significant increase in cytotoxicity (based on mitochondrial MTT reduction and lactate dehydrogenase-leakage [LDH]) at concentrations >2.5 uM that could explain in part the apparent inhibitory effect on aromatase activity. Compared to 6-OH-BDE47, the methoxy analog (6-CH(3)O-BDE47) did not elicit a cytotoxic effect, whereas significant inhibition of aromatase remained. TBP caused a concentration-dependent induction of aromatase activity between 0.5 and 7.5 uM (with a maximum of 3.8-fold induction at 7.5 uM). This induction was not observed when a OH- group replaced the CH(3)O- group or when bromine atoms adjacent to this OH- group were absent... |
| Fish/Seafood Concentrations | Endeavour prawns from Exmouth Gulf, Shark Bay, and Groote Elylandt, Australia, contained 4-bromophenol at concentrations of 61 to 410, 370, and 370 ug/kg, respectively(1). Ten different species of fish, collected in August 1992 from the eastern coast of Australia, contained 4-bromophenol at concentrations of <0.05 to 0.2 ng/g for the carcass and <0.05 to 100 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 omnivoresconcentrations in the flesh ranged from <0.01 to 1.6 ng/g, <0.01 to 46 ng/g, <0.01 to 1.2, and <0.01 to 0.1 ng/g, respectively, while concentrations in the gut ranged from <0.01 to 1.1 ng/g, <0.01 to 2300 ng/g, <0.01 to 56 ng/g, and <0.01 to 0.8 ng/g, respectively(3). Thirty samples of 9 species of prawns, collected from the eastern coast of Australia from 1993 to 1996, contained 4-bromophenol at concentrations of <0.01 to 850 ng/g(4). 4-Bromophenol concentrations in cultivated prawns ranged from <0.01 to 0.56 ng/g in the head and <0.01 to 0.06 ng/g in the tail(4). 4-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) was 0 ng/g (not detected) for eachin the gut, concentrations ranged from 0 to 206 ng/g and 0 ng/g, respectively. In the mullusks, including clams (Tapes philippinarum) and oysters (Ostrea rivularis), seasonal concentrations ranged from 0 to 55.6 ng/g and 0 ng/g, respectively. For crustaceans, seasonal concentrations in the cephalothorax and tail of the shrimp (Penaeus japonicus) ranged from 0 to 9.47 ng/g and 0 to 5.39 ng/g, respectivelyin crab (Charybdis feriatus), concentrations ranged from 0 to 47.9 ng/g(5). |
| Artificial Pollution Sources | 4-Bromophenol's production and use as a disinfectant(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: 4-Bromophenol, present at 100 mg/L, reached 0% of its theoretical BOD in 14 days using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). A 93% ring degradation was reported for 4-bromophenol, present at 100 mg/L, over a 1-day incubation period measured with UV absorption in sludge from aerated soil where glucose and peptone were added in mineral salts(2). A first order rate constant of 4.47X10-4 1/hours was determined for 4-bromophenol in unacclimated activated sludge(3). A first order rate constant of 1.57X10-3 was calculated for 4-bromophenol, present at 50 ppm, in cresol activated sludge at a pH of 7.2 in a 5-day period. This corresponds to a half life of 18.4 days(4). 4-Bromophenol, present at 400 mg/L degraded by <20% in 28 days in activated sludge as measured by DOC analysis, where DOC was present at 1000 COD-mg/L and the concentration of microbial population was 1 g/L(5). 4-Bromophenol, present at 50 ppm, reached 100% UV disappearance in 16 days using a Dunkirk soil inoculum with a microbial population of 4 g soil/L mineral salts media(6). Grab samples, which contained 10+7 to 10+9 organisms per liter were obtained from 5 ponds or rivers within 10 km from Athens, GA. 4-Bromophenol, present at 1 ppm, was found to degrade by 9.6, 9.6, 7.9, 9.9, and 8.2 E-11 liter/organisms per hour(7). |
| Environmental Bioconcentration | An experimental BCF of 8.0 to 12 was calculated in fish for 4-bromophenol using carp (Cyprinus carpio) which were exposed over a 6-week period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| F | 8-10-23 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | SJ7960000 |
| UN transport number | 2811 |
| Customs code | 29081000 |
| Toxicity | mouse,LD50,intraperitoneal,411mg/kg (411mg/kg),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Hazard symbols | Xn,Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-37/39-36 |
| Hazard class | 6.1(b)Acute Tox. 4 OralSkin Irrit. 2 |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| GHS hazard statements | H302-H315-H319-H361-H411 |
| GHS precautionary statements | P501-P273-P270-P202-P201-P264-P280-P302+P352-P391-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P405 |
| Hazardous substances data | 106-41-2(Hazardous Substances Data) |
Applications & Uses
Uses
4-Bromophenol is used as an intermediate in medicine grade. It is also used as a phenol that is used in Stille reactions. It is used in the intermediate of organic synthesis, flame retardant and pharmaceutical industry.
Preparation & Synthesis
Preparation
4-Bromophenol is synthesized by bromination of phenol. The bromine and carbon disulfide solution was added to the phenolic carbon disulfide solution, and the addition was started below 5°C, and the addition was completed under stirring for 2 hours. Phenol and bromine are approximately equimolar ingredients. Distill the reactant to remove carbon disulfide, and then conduct fractional distillation under reduced pressure to collect fractions at 145-150°C (3.32-3.99kPa) to obtain the product. Yield 80-84%.