11H-Benzo[a]fluorene

216.28

216.28

205-944-9

65EP6ZT62K

1453

89262

DTXSID3075204

White or off-white powder|Platelets from acetone or acetic acid|Colorless plate like crystals|Beige powder[Sigma-Aldrich; Product Information for 11H-Benzo

2902909090

0

5.32

COLOURLESS PLATE-LIKE CRYSTALS.

1.2±0.1 g/cm3

189 °C

399 °C

11 °C

1.714

dioxane: soluble 0.1g/10 mL, clear, colorless

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

2.43e-07 mmHg

2.66e-05 atm-m3/mole

Enthalpy of sublimation: 105.4 kJ/mol at 383 K; Enthalpy of fusion: 18.4 kJ/mol at 462.8 K|Henry's Law constant = 1.54X10-6 atm-cu m/mole at 25 °C (estimated from vapor pressure and water solubility)|Hydroxyl radical reaction rate constant = 4.7X10-11 cu-cm/molc sec at 25 °C

Enthalpy of vaporization: 83.7 kJ/mol at 398 K

III

6.1(b)

2811

3

11-23/24/25-39/23/24/25

36/37-45

DF6382000

F,T

Keep in a well-ventilated room.

Stable under recommended storage conditions.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

P273, P391, P501

H400

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

Not combustible.

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|Skin protection: Handle with gloves.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|General industrial hygiene practice.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo|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. Ensure that the local ventilation moves the contaminant away from the worker.

Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Keep in a well-ventilated room.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.

PREVENT DISPERSION OF DUST! AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

Benzo(a)fluorene has been identified in gasoline engine exhaust at concentrations of 82-136 ug/L fuel(1). Gaseous emissions from gasoline-powered chain saws had benzo(a)fluorene concentrations ranging from 2.6-16 ug/cu m(2). Two turbine engine exhaust had benzo(a)fluorene levels of 3.31 and 16.19 ng/cu m(3). Benzo(a)fluorene was qualitatively identified in effluents from biomass gasifiers(4).

SEDIMENT: Sediment collected from the Saudafjord, Norway in 1976 (0-8 cm depth) contained benzo(a)fluorene concentrations of 0.9-110.0 ppb(1). Surface sediments collected from estuaries of three rivers and a port the Niigata Prefecture, Japan in Sept 1995 contained benzo(a)fluorene (concentration not reported)(2). Analysis of sediments collected from the Inner Harbor Navigation Canal (Lake Pontchartrain, LA) in May-June 1980 detected a benzo(a)fluorene level of 21 ng/g dry wt(3). Sediment core samples taken from Woods Lake (a remote lake in NY State's Adirondack Park) in 1978 had benzo(a)fluorene concentrations ranging from 290 ng/g dry wt (0-4 cm depth) to 2 ng/g (80-84 cm depth)(4).

URBAN/SUBURBAN: Year-round ambient air sampling conducted in Japan in 1977-1978 detected benzo(a)fluorene + benzo(b)fluorene concentrations of 2.40-15.7 ng/cu m in the vapor-phase and 0.15-4.28 ng/cu m in the particulate-phase(1). Air samples collected in Antwerp, Belgium in 1974-1975 contained benzofluorene concentrations of 1.60 ng/cu m in the summer and 19.69 ng/cu m in the winter(2). Air sample collected over an urban area of the Northern Chesapeake Bay in June 1996 contained a benzofluorene concentration of about 0.4-0.5 ng/cu m(3). Benzo(a)fluorene was detected in Chicago, IL urban air samples collected in 1994-1995 (concentration not reported)(4).|INDOOR AIR: Analysis of wood-heated sauna air identified benzo(a)fluorene in both the vapor and particulate phases with concentrations ranging from 0.2-34 ug/cu m(1).|RURAL/REMOTE: Air samples collected in Botrange, Belgium in 1974-1975 contained benzofluorene concentrations of 0.82 ng/cu m in the summer and 2.36 ng/cu m in the winter(1). Samples of sea air collected near Ostend, Belgium in 1974-1975 contained benzofluorene concentrations of 10.21 ng/cu m in the winter(1).|SOURCE DOMINATED: Inhalable air particulate matter collected in Bahrain during July-Aug 1991 during the burning of oil fields in Kuwait contained benzo(a)fluorene concentrations of <0.05 ng/cu m(1).

Benzo(a)fluorene has been identified in mainstream cigarette smoke (at concentrations of 4.1 ug/100 cigarettes, 4.9 ug/100 cigarettes, 184 ng/cigarette) in sidestream cigarette smoke (751 ng/cigarette), cigarette smoke-polluted rooms (39 ng/cu m), smoke of marijuana cigarettes (4.2 ug/100 cigarettes), in lubricating oils (2.67 mg/kg) and in crude oils (10.8 mg/kg)(1).|Benzo(a)fluorene was identified in wood smoke generated from burning mesquite wood (66 ug/kg burned) and hickory wood (24 ug/kg burned)(1) and in soot produced by the combustion of polystyrene, polypropylene and wood(2). Analysis of liquid flavorings used for smoking detected a benzo(a)fluorene concentration 0.49 ug/kg derived from poplar wood(3). Benzo(a)fluorene was identified in coal tar(4). Analysis of a Swedish diesel fuel identified a benzo(a)fluorene concentration of 0.1 mg/L(5). A maximum benzo(a)fluorene concentration of 0.082 mg/g soot was detected in soot extracts from domestic coal-burning stoves of Henan Province, China(6).

IDENTIFICATION AND USE: Benzo(a)fluorene is a polycyclic aromatic hydrocarbon (PAH). It does not have a commercial use, other than in biochemical research of PAH. HUMAN STUDIES: Benzo(a)fluorene is present as a minor component of the total content of polynuclear aromatic compounds in the environment. Human exposure to benzo(a)fluorene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated with combustion products. ANIMAL STUDIES: Benzo(a)fluorene was tested for carcinogenicity in mice in one study by skin application and in a mouse-skin initiation-promotion assay. Negative results were obtained in both studies. In a study involving subcutaneous administration of benzo(a)fluorene to mice, no injection-site tumor was observed. The available data were inadequate to evaluate the mutagenicity of benzo(a)fluorene to Salmonella typhimurium. ECOTOXICITY STUDIES: Benzo(a)fluorene is a known aryl hydrocarbon receptor (AhR) agonist.

/AQUATIC SPECIES/ In the present study, effect-directed analysis was used to identify teratogenic compounds in porewater collected from a Superfund site along the Elizabeth River estuary (VA, USA). Zebrafish (Danio rerio) exposed to the porewater displayed acute developmental toxicity and cardiac teratogenesis, presumably because of elevated sediment levels of polycyclic aromatic hydrocarbons (PAHs) from historical creosote use. Pretreatment of porewater with several physical and chemical particle removal methods revealed that colloid-bound chemicals constituted the bulk of the observed toxicity. Size-exclusive chromatography and normal-phase high-performance liquid chromatography were used to fractionate Elizabeth River porewater. Acute toxicity of porewater extracts and extract fractions was assessed as the pericardial area in embryonic zebrafish. The most toxic fraction contained several known aryl hydrocarbon receptor (AhR) agonists (e.g., 1,2-benzofluorene and 1,2-benzanthracene) and cytochrome P450 A1 (CPY1A) inhibitors (e.g., dibenzothiophene and fluoranthene). The second most toxic fraction contained known AhR agonists (e.g., benzo[a]pyrene and indeno[1,2,3-cd]pyrene). Addition of a CYP1A inhibitor, fluoranthene, increased toxicity in all active porewater fractions, suggesting synergism between several contaminants present in porewaters. The results indicate that the observed acute toxicity associated with Elizabeth River porewater results from high concentrations of AhR agonistic PAHs and mixture effects related to interactions between compounds co-occurring at the Elizabeth River site. However, even after extensive fractionation and chemical characterization, it remains plausible that some active compounds in Elizabeth River porewater remain unidentified.

Benzo(a)fluorene occurs in fossil fuels and crude oils(1). Polyaromatic hydrocarbons (PAHs) also occur in volcanic eruptions(2,3).

There is no commercial production or known use for benzo(a)fluorene(1). Benzo(a)fluorene occurs ubiquitously as a product of incomplete combustion(1). It has been identified in mainstream cigarette smoke(1,4), sidestream cigarette smoke, cigarette smoke-polluted rooms, smoke of marijuana cigarettes and gasoline engine exhaust(1). Benzo(a)fluorene is emitted in smoke from burning wood, plastics(2) and coal(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc value of 2.88X10+5(1) indicates that benzo(a)fluorene is expected to be immobile in soil(SRC). Volatilization of benzo(a)fluorene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.54X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.43X10-7 mm Hg(3), and water solubility, 0.045 mg/L(4). In addition, adsorption to soil is expected to attenuate potential volatilization(SRC). Benzo(a)fluorene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Polycyclic aromatic hydrocarbons (PAHs), such as benzo(a)fluorene, with more than 3 rings appear to be extremely stable to biodegradation(5). Breakdown in soil generally takes weeks to months for PAHs with 3 rings, primarily by action of microorganisms; PAHs with 4 or more rings are generally resistant to biodegradation(6,7). Benzo(a)fluorene absorbs light strongly at wavelengths >290 nm(8) and, therefore, is expected to be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).|AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value of 2.88X10+5(1) indicates that benzo(a)fluorene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.43X10-7 mm Hg(4), and water solubility, 0.045 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 35 and 260 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is >10 years if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 2600(SRC), from a log Kow of 5.68(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). However, benzo(a)fluorene may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(10). Polycyclic aromatic hydrocarbons (PAHs) with four or more rings, such as benzo(a)fluorene, are generally expected to be resistant to biodegradation(11,12). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Benzo(a)fluorene absorbs strongly at wavelengths >290 nm(13), and therefore is expected to be susceptible to direct photolysis at water surfaces exposed to sunlight(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzo(a)fluorene, which has a vapor pressure of 2.43X10-7 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere. Ambient air monitoring has detected benzo(a)fluorene in both the vapor and particulate phases(3). Vapor-phase benzo(a)fluorene 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 8.3 hours(SRC), calculated from its rate constant of 4.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase benzo(a)fluorene may be removed from the air by wet and dry deposition(SRC). Benzo(a)fluorene absorbs strongly at wavelengths >290 nm(5) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of benzo(a)fluorene with photochemically-produced hydroxyl radicals has been estimated as 4.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Benzo(a)fluorene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups that hydrolyze under environmental conditions(2). Benzo(a)fluorene absorbs light strongly at wavelengths >290 nm(3,4) and, therefore, is expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 2600 was calculated in fish for benzo(a)fluorene(SRC), using a log Kow of 5.68(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). However, benzo(a)fluorene may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(4). Using a database of measured fish biotransformation half-lives of PAHs(5), a fish biotransformation half-life of 0.8 days has been estimated for benzo(a)fluorene(2).

Benzo(a)fluorene has a reported experimental Koc of log 5.46 (Koc = 2.88X10+5)(1). According to a classification scheme(2), this Koc value suggests that benzo(a)fluorene is expected to be immobile in soil(SRC).

The Henry's Law constant for benzo(a)fluorene is estimated as 1.54X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.43X10-7 mm Hg(1), and water solubility, 0.045 mg/L(2). This Henry's Law constant indicates that benzo(a)fluorene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 35 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 260 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is >10 years if adsorption is considered (4). Air-water interface monitoring conducted in the Chesapeake Bay during 1996-1997 indicated that volatilization of benzo(a)fluorene can occur(5). Benzo(a)fluorene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Benzo(a)fluorene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Benzo(a)fluorene was qualitatively detected in groundwater samples collected from a contaminated aquifer in St. Louis Park, MN near a coal-tar distillation facility(1).|DRINKING WATER: Benzo(a)fluorene has been identified in tap water at concentrations of <5 ng/L(1). Tap water collected in Ottawa, Canada in 1978 was analyzed for PAHs, but benzo(a)fluorene was not detected (detection limit not reported)(2).|RAIN/SNOW: Benzo(a)fluorene was detected in snow core samples collected at remote areas of five mountain lakes in Europe (Alps, Pyrenees, Caledonia)(1).

Mean benzo(a)fluorene concentrations of 0.2-3.3 ug/kg (fresh wt) were detected in lettuce grown at sites near highways in Sweden(1); results of the monitoring study suggested that food plants grown near highways with high volumes of traffic may become contaminated with PAHs released from vehicle exhaust(1). Benzo(a)fluorene concentrations of 17-28 and 1-2 ug/kg were detected in beef patties grilled over mesquite wood fire and hardwood charcoal respectively(2). Six olive oils and seven virgin olive oils (most consumed in Itlay) were analyzed for PAHs, and benzo(a)fluorene concentrations of 2-27 ug/kg were detected in two olive oils, but was not detected in any other(3).

Occupational exposure to benzo(a)fluorene may occur through inhalation and dermal contact with this compound at workplaces where benzo(a)fluorene is produced as a product of incomplete combustion of organic fuels. Monitoring data indicate that the general population may be exposed to benzo(a)fluorene via inhalation of ambient air, inhalation of tobacco smoke, ingestion of food and dermal contact with particulate matter resulting from combustion(SRC). Since benzo(a)fluorene is a product of incomplete combustion(1), occupational situations involving heating organic material may result in exposure to this compound through inhalation of air particulate matter and dermal contact with combustion products(SRC).|Benzo(a)fluorene was found to be completely in the particulate phase in the workplace air of an aluminum plant at Soderbert, Norway at an average concentration of 1.5 ug/cu m(1).

140.99 Days

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

/OTHER TOXICITY INFORMATION/ Benzo(a)fluorene is present as a minor component of the total content of polynuclear aromatic compounds in the environment. Human exposure to benzo(a)fluorene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated with combustion products.

1,2-benzofluorene

The substance can be absorbed into the body by inhalation of its aerosol.

See Effects of long-term or repeated exposure.

Redness. Pain.