205-99-2 Usage
Description
BENZO(B)FLUORANTHENE, also known as Benz[e]acephenanthrylene, is a polycyclic aromatic hydrocarbon characterized by its orthoand peri-fused polycyclic arene structure, consisting of a benzene ring fused with an acephenanthrylene ring. It is typically found in airborne pollutants, auto exhaust, and tobacco and marijuana smoke. This colorless to pale yellow to yellow-orange needle-shaped solid exhibits physical properties that make it a significant environmental contaminant.
Uses
Used in Environmental Monitoring:
BENZO(B)FLUORANTHENE is used as a biomarker for environmental pollution, particularly in the assessment of air quality and the presence of hazardous substances in the atmosphere. Its detection in significant levels in various sources such as auto exhaust and smoke emissions helps in understanding the extent of pollution and implementing necessary measures to control it.
Used in Research and Analysis:
BENZO(B)FLUORANTHENE serves as a subject of study in scientific research, particularly in the fields of environmental chemistry, toxicology, and epidemiology. Its chemical properties and potential health effects are investigated to better understand the risks associated with exposure to this pollutant and to develop strategies for mitigating its impact on human health and the environment.
Synthesis Reference(s)
Tetrahedron Letters, 36, p. 2403, 1995 DOI: 10.1016/0040-4039(95)00314-3
Air & Water Reactions
Insoluble in water.
Reactivity Profile
BENZO(B)FLUORANTHENE can react with strong oxidizing agents. May react with electrophiles, peroxides, nitrogen oxides and sulfur oxides
Hazard
Confirmed carcinogen.
Health Hazard
Acute oral toxicity data are not available.There is sufficient evidence on the carcinogenicity of this compound in animals. Itproduced tumors at the site of application.Cancers in lungs and skin have been observedin animals.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition, BENZO(B)FLUORANTHENE emits acrid smoke and irritating fumes.
Fire Hazard
Flash point data for BENZO(B)FLUORANTHENE are not available; however, BENZO(B)FLUORANTHENE is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
tumorigenic data. Mutation data reported.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Potential Exposure
There is no commercial production of
this compound. Benzo(b)fluoranthene is a chemical substance
formed during the incomplete burning of fossil fuel,
garbage, in cigarette smoke, or any organic matter and is
Benzofluoranthene 399
found in smoke in general; it is carried into the air, where
it condenses onto dust particles and is distributed into water
and soil and on crops. B(b)F is a PAH and a component of
coal tar pitch used in industry as a binder for electrodes. It
is also a component of creosote, which is used to preserve
wood. PAHs are also found in limited a mounts in bituminous
materials and asphalt used for paving, roofing, and
insulation. B(b)F has some use as a research chemical. It is
available from some specialty chemical firms in low quantities
(25 100 mg).
Carcinogenicity
Benzo[b]fluoranthenewas tested
for carcinogenicity by dermal application in mice in multiple
studies, intraperitoneal injection into mice
in multiple studies, and intrapulmonary
implantation into rats in one study. In all of these studies,
benzo[b]-fluoranthene exhibited a significant carcinogenic
activity.
Source
Benzo[b]fluoranthene and benzo[k]fluoranthene were detected in 8 diesel fuels at
concentrations ranging from 0.0027 to 3.1 mg/L with a mean value of 0.266 mg/L (Westerholm
and Li, 1994). Also present in low octane gasoline (0.16–0.49 mg/kg), high octane gasoline (0.26–
1.34 mg/kg), used motor oil (2.8–141.0 mg/kg), and bitumen (40 to 1,600 ppb), cigarette smoke (3
g/1,000 cigarettes), and gasoline exhaust (19 to 48 g/L) (quoted, Verschueren, 1983). Also
detected in asphalt fumes at an average concentration of 22.04 ng/m3 (Wang et al., 2001).
Nine commercially available creosote samples contained benzo[b]fluoranthene at concentrations
ranging from 2 to 96 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[b]fluoranthene were 0.790 mg/kg of pine burned, 0.400 mg/kg of oak
burned, and 0.327 mg/kg of eucalyptus burned.
Particle-phase tailpipe emission rate from a noncatalyst-equipped gasoline-powered automobile
was 37.3 μg/km (Schauer et al., 2002).
Environmental fate
Biological. Ye et al. (1996) investigated the ability of Sphingomonas paucimobilis strain U.S.
EPA 505 (a soil bacterium capable of using fluoranthene as a sole source of carbon and energy) to
degrade 4, 5, and 6-ringed aromatic hydrocarbons (10 ppm). After 16 h of incubation using a
resting cell suspension, only 12.5% of benzo[b]fluoranthene had degraded. It was suggested that
degradation occurred via ring cleavage resulting in the formation of polar metabolites and carbon
dioxide.
Soil. The reported half-lives for benzo[b]fluoranthene in a Kidman sandy loam and McLaurin
sandy loam are 294 and 211 d, respectively (Park et al., 1990).
Photolytic. The atmospheric half-life was estimated to range from 1.43 to 14.3 h (Atkinson,
1987).
Chemical/Physical. Benzo[b]fluoranthene will not hydrolyze because it has no hydrolyzable
functional group (Kollig, 1993).
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.
Waste Disposal
Residues and sorbent media
may be packaged in 17H epoxy-lined drums and disposed
of at an EPA-approved site. Destroy by permanganate oxidation,
high-temperature incineration with scrubbing equipment,
or microwave plasma treatment, if available.
Confirm disposal procedures with responsible environmental
engineer and regulatory officials.
Check Digit Verification of cas no
The CAS Registry Mumber 205-99-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,0 and 5 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 205-99:
(5*2)+(4*0)+(3*5)+(2*9)+(1*9)=52
52 % 10 = 2
So 205-99-2 is a valid CAS Registry Number.
InChI:InChI=1/C20H12/c1-2-7-14-13(6-1)12-19-16-9-4-3-8-15(16)18-11-5-10-17(14)20(18)19/h1-12H
205-99-2Relevant articles and documents
Regioselective Activation of a Sterically More Hindered C?C Bond of Biphenylenes Using an Alkene as Both a Directing Group and a Reaction Moiety
Takano, Hideaki,Ito, Takeharu,Kanyiva, Kyalo Stephen,Shibata, Takanori
, p. 15173 - 15177 (2018)
The Rh-catalyzed intramolecular reaction of 1-(2-vinylaryl)-substituted biphenylenes was used to construct a dihydrobenzo[b]fluoranthene skeleton. This transformation was achieved by regioselective C?C bond cleavage of a sterically more hindered biphenylene site by using alkene as both a directing group and a reaction moiety. Furthermore, we measured and analyzed the photophysical properties of the new multicyclic fused compounds.
Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics
Chatterjee, Tanmay,Lee, Da Seul,Cho, Eun Jin
, p. 4369 - 4378 (2017/04/28)
Herein we report an extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation of a wide variety of polycyclic (hetero)aromatic compounds, including phenanthrenes, in moderate to high yields. This procedure is amenable to gram-scale synthesis of 9-phenylphenanthrene.
Tandem [4 + 2]/[2 + 2] cycloaddition reactions involving indene or benzofurans and arynes
Bhojgude, Sachin Suresh,Thangaraj, Manikandan,Suresh, Eringathodi,Biju, Akkattu T.
supporting information, p. 3576 - 3579 (2014/07/21)
The reaction of arynes with indene/benzofurans has been developed. The arynes were generated from 2-(trimethylsilyl)aryl triflates by the fluoride-induced 1,2-elimination react with indene or various benzofurans proceeding via a cascade reaction involving
