| Identification | More | [Name]
1,2-BENZANTHRACENE | [CAS]
56-55-3 | [Synonyms]
1,2-BENZANTHRACENE
2,3-BENZOPHENANTHRENE
BENZ[1,2]ANTHRACENE
BENZ[A]ANTHRACENE
BENZ A ANTHRENE
BENZ[ALPHA]ANTHRACENE
Benzanthracene
BENZANTHRENE
BENZO(A)ANTHRACENE
NAPHTHANTHRACENE
TETRAPHENE
1,2-benz(a)anthracene
1,2-Benz[a]anthracene
1,2-Benzanthrazen
1,2-Benzanthrene
1,2-Benzoanthracene
2,3-Benzphenanthrene
benz(b)phenanthrene
benzanthracene(non-specificname)
benzo(b)phenanthrene | [EINECS(EC#)]
200-280-6 | [Molecular Formula]
C18H12 | [MDL Number]
MFCD00003599 | [Molecular Weight]
228.29 | [MOL File]
56-55-3.mol |
| Chemical Properties | Back Directory | [Description]
1,2-Benzanthracene is available as colourless to yellow-brown fluorescent flakes or powder.
It is stable, combustible, and incompatible with strong oxidising agents. On decomposition,
1,2-benzanthracene releases carbon monoxide, carbon dioxide, acrid smoke, and
fumes. Exposures may cause irritation
of the eyes, skin, and respiratory tract. | [Appearance]
Benz(a)anthracene is a colorless plate-like
material which is recrystallized from glacial acetic acid or
a light yellow to tan powder. PAHs are compounds containing
multiple benzene rings and are also called polynuclear
aromatic hydro carbons. | [Melting point ]
157-159 °C(lit.)
| [Boiling point ]
437.6 °C(lit.)
| [density ]
1.274 g/cm3 | [vapor pressure ]
54.8 (de Kruif, 1980) | [refractive index ]
1.7710 (estimate) | [Fp ]
-18 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Soluble in ethanol, ether, acetone, benzene (U.S. EPA, 1985), toluene, xylenes, and other
monoaromatic hydrocarbons. | [form ]
Solid | [pka]
>15 (Christensen et al., 1975) | [color ]
Light Yellow | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
9.4ug/L(25 ºC) | [Merck ]
1062 | [BRN ]
1909298 | [Henry's Law Constant]
1.48, 3.06, 6.22, 12.0, and 20.8 at 4.1, 11.0, 18.0, 25.0, and 31.0 °C, respectively (Bamford et al.,
1998) | [CAS DataBase Reference]
56-55-3(CAS DataBase Reference) | [IARC]
2B (Vol. 92, Sup 7) 2010 | [EPA Substance Registry System]
Benz[a]anthracene (56-55-3) |
| Hazard Information | Back Directory | [Chemical Properties]
1,2-Benzanthracene is available as colorless to yellow brown fl uorescent fl akes or powder. It is stable, combustible, and incompatible with strong oxidizing agents. On decomposition, 1,2-benzanthracene releases carbon monoxide, carbon dioxide, acrid smoke, and
fumes. During work, 1,2-benzanthracene can be absorbed into the body of occupational
workers by inhalation, through the skin, and by ingestion. Exposures may cause irritation
to the eyes, skin, and respiratory tract. | [General Description]
Colorless leaflets or plates or coarse gold powder with a greenish-yellow fluorescence. May reasonably be expected to be a carcinogen. | [Reactivity Profile]
BENZ[A]ANTHRACENE 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. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Confirmed carcinogen. Found in oils,
waxes, smoke, food, drugs.
| [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and irritating fumes. | [Health Hazard]
Exposures to 1,2-benzanthracene is known to cause kidney damage. However, published data on the neurotoxicity, teratogenicity, reproductive toxicity, and mutagenicity of
1,2-benzanthracene is not available. | [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. | [Fire Hazard]
Flash point data for this chemical are not available. BENZ[A]ANTHRACENE is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed. As
first aid for pulmonary edema, a doctor or authorized paramedic
may consider administering a drug or other inhalation
therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1—Poisonous materials, Technical
Name Required. | [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. | [Physical properties]
Colorless leaflets or plates with a greenish-yellow fluorescence | [Uses]
Benz[a]anthracene is a PAH that has carcinogenic properties. It is also used in the synthesis of anti-tumor agents. | [Uses]
Benz[a]anthracene is primarily used in research. | [Definition]
ChEBI: Tetraphene is an angular ortho-fused polycyclic arene consisting of four fused benzene rings. It is an ortho-fused polycyclic arene and a member of tetraphenes. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 27, p. 3716, 1962 DOI: 10.1021/jo01057a528 | [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). | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xn,F | [Risk Statements ]
R45:May cause cancer.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R38:Irritating to the skin.
R11:Highly Flammable.
R63:Possible risk of harm to the unborn child.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
CV9275000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29029000 | [storage]
Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers
tightly closed | [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. | [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. | [Hazardous Substances Data]
56-55-3(Hazardous Substances Data) | [Toxicity]
LD50 for mice by intravenous injection 10 mg/kg (Patnaik, 1992). |
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