56-55-3

Physical properties

Colorless leaflets or plates with a greenish-yellow fluorescence

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 3716, 1962 DOI: 10.1021/jo01057a528

General Description

Colorless leaflets or plates or coarse gold powder with a greenish-yellow fluorescence. May reasonably be expected to be a carcinogen.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,2-BENZANTHRACENE may react vigorously with strong oxidizing agents. Can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

Hazard

Confirmed carcinogen. Found in oils, waxes, smoke, food, drugs.

Health Hazard

There is no report on its oral toxicity.However, it may be highly toxic by intravenous administration. A lethal dose in miceis reported as 10 mg/kg. Its carcinogenicactions in animals is well established. Subcutaneous administration of 1,2-BENZANTHRACENEin mice resulted in tumors at the sites ofapplicationFlesher and Myers (1990) have correlatedcarcinogenic activity of benzo[a]anthraceneto its bioalkylation at the site of injection.Male rats were dosed subcutaneously andthe tissue in contact with the hydrocarbonwas visualized after 24 hours under UV light.Bioalkylation or the biochemical introductionof an alkyl group occurred at the mesoanthracenic centers, which are the most reactivesites in the molecule.

Fire Hazard

Flash point data for 1,2-BENZANTHRACENE are not available. 1,2-BENZANTHRACENE is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data by skin contact and other routes. Poison by intravenous route. Human mutation data reported. It is found in oils, waxes, smoke, food, drugs. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Benz(a)anthracene is a contaminant and does not have any reported commercial use or application, although one producer did report the substance for the Toxic Substances Control Act Inventory. Benz(a)anthracene has been reported present in cigarette smoke condensate, automobile exhaust gas; soot; and the emissions from coal and gas works and electric plants. Benz(a)anthracene also occurs in the aromatic fraction of mineral oil, commercial solvents, waxes, petrolatum, creosote, coal tar; petroleum asphalt; and coal tar pitch. Microgram quantities of benz(a)anthracene can be found in various foods, such as charcoal broiled, barbecued, or smoked meats and fish; certain vegetables and vegetable oils, roasted coffee, and coffee powders. Human subjects are exposed to benz(a) anthracene through either inhalation or ingestion. Workers at facilities with likely exposure to fumes from burning or heating of organic materials have a potential for exposure to benz(a)anthracene. Consumers can be exposed to this chemical through ingestion of various foods, with concentrations of 100 μg/kg in some instances. Cigarette smoke condensate has quantities of benz(a)anthracene that range from 0.03 to 4.6 μg/g. Benz(a)anthracene is found in the atmosphere at levels that vary with geography and climatology. These values can range from up to 136 μg/1000 m3 in summer to 361 μg/1000 m3 in winter. Drinking water samples may contain up to 0.023 μg/L benz(a)anthracene, and surface waters have been found to contain 0.004 0.185 μg/L. The soil near industrial centers has been shown to contain as much as 390 μg/kg of Benz(a)anthracene, whereas soil near highways can have levels of up to 1500 μg/kg, and areas polluted with coal tar pitch can reach levels of 2500 mg/kg.

Carcinogenicity

BA’s metabolites are genotoxic in the Ames mutation test and caused unscheduled DNA synthesis in primary rat hepatocytes.In an in vivo mutagenic assay, male CD rats (6/group) were dosed three times with BA over a 24-hour interval by intratracheal instillation. Lung cells were enzymatically separated and used to determine the frequency of DNA adducts, sister chromatid exchanges (SCEs), and micronuclei. BA induced DNA adducts, SCEs, and micronuclei in this rat lung cell system.Benz(a)anthracene is designated an A2- suspected human carcinogen by ACGIH and has no assigned threshold limit value.

Source

Concentrations in 8 diesel fuels ranged from 0.018 to 5.9 mg/L with a mean value of 0.93 mg/L (Westerholm and Li, 1994). Identified in Kuwait and South Louisiana crude oils at concentrations of 2.3 and 1.7 ppm, respectively (Pancirov and Brown, 1975). The concentration of benzo[a]anthracene in coal tar and the maximum concentration reported in groundwater at a mid-Atlantic coal tar site were 3,900 and 0.0079 mg/L, respectively (Mackay and Gschwend, 2001). Based on laboratory analysis of 7 coal tar samples, benzo[a]anthracene concentrations ranged from 600 to 5,100 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentrations of <1,500 and 850 mg/kg, respectively (Nelson et al., 1996). Lehmann et al. (1984) reported benzo[a]anthracene concentrations of 7.3 mg/g in a commercial anthracene oil and 8,400 to 13,100 mg/kg in three road tars. Also identified in high-temperature coal tar pitches used in roofing operations at concentrations ranging from 169,000 to 324,000 mg/kg (Malaiyandi et al., 1982). Detected in asphalt fumes at an average concentration of 53.49 ng/m3 (Wang et al., 2001). Nine commercially available creosote samples contained benzo[a]anthracene at concentrations ranging from 39 to 950 mg/kg (Kohler et al., 2000). Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The particle-phase emission rates of benzo[a]anthracene were 1.22 mg/kg of pine burned, 0.630 mg/kg of oak burned, and 0.533 mg/kg of eucalyptus burned. The gas-phase emission rate was 0.032 mg/kg of eucalyptus burned. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 0.181 and 4.80 μg/km, respectively (Schauer et al., 2002). Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned in a fluidized bed reactor at seven different temperatures (50 °C increments) beginning at 650 °C. The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%) and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the amount of benzo[a]anthracene emitted ranged from 91.2 ng/kg at 650 °C to 461.3 ng/kg at 750 °C. The greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999).

Environmental fate

Biological. In an enclosed marine ecosystem containing planktonic primary production and heterotrophic benthos, the major metabolites were water soluble and could not be extracted with organic solvents. The only degradation product identified was benzo[a]anthracene-7,12-dione (Hinga and Pilson, 1987). Under aerobic conditions, Cunninghanella elegans degraded benzo[a]anthracene to 3,4-, 8,9-, and 10,11-dihydrols (Kobayashi and Rittman, 1982; Riser- Roberts, 1992). Soil. The half-lives for benzo[a]anthracene in a Kidman sandy loam and McLaurin sandy loam were 261 and 162 d, respectively (Park et al., 1990). Surface Water. In a 5-m deep surface water body, the calculated half-lives for direct photochemical transformation at 40 °N latitude, in the midsummer during midday were 4.8 and 22.8 h with and without sediment-water partitioning, respectively (Zepp and Schlotzhauer, 1979). Photolytic. Benzo[a]anthracene-7,12-dione formed from the photolysis of benzo[a]an-thracene (λ = 366 nm) in an air-saturated, acetonitrile-water solvent (Smith et al., 1978). Chemical/Physical. Benzo[a]anthracene-7,12-dione and a monochlorinated product were formed during the chlorination of benzo[a]anthracene. At pH 4, the reported half-lives at chlorine concentrations of 0.6 and 10 mg/L were 2.3 and <0.2 h, respectively (Mori et al., 1991). When an aqueous solution containing benzo[a]anthracene (16.11 μg/L) was chlorinated for 6 h using chlorine (6 mg/L), the concentration was reduced 53% (Sforzolini et al., 1970).

storage

Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed

Purification Methods

Crystallise 1,2-benzanthracene from MeOH, EtOH or *benzene (charcoal), then chromatograph it on alumina from sodium-dried *benzene (twice), using vacuum distillation to remove *benzene. Final purification is by vacuum sublimation. [Beilstein 5 IV 2549.]

Toxicity evaluation

Benz[a]anthracene is not synthesized commercially. The primary source of many PAHs in air is the combustion of wood and other fuels. PAHs released into the atmospheremay deposit onto soil or water. In surface water, PAHs can volatilize, bind to suspended particles, or accumulate in aquatic organisms. Adsorption to solid particles in the soil extended their half-life, benz[a]anthracene’s half-life in Kidman sandy loam is 261 days. The vapor pressure of benz[a]anthracene is 1.9×106mmHg at 25°C, and it has an atmospheric half-life of about 7.7 h due primarily to photochemical degradation.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Powder can form an explosive mixture with air.

Waste Disposal

Atomize into incinerator with a flammable liquid.

Precautions

Workers should wash thoroughly after using and handling 1,2-benzanthracene. Use only in a well-ventilated area. Minimize dust generation and accumulation. Avoid contact with the eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.