205-99-2

Usage

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 BENZO(B)FLUORANTHENE 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 BENZO(B)FLUORANTHENE. 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.

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

Synthetic route

(4aα,8bα,9β,13bβ)-8b,9-dihydro-9,13b-epoxy-13bH-benzo<3,4>cyclobuta<1,2-k>phenanthrene → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 0.0833333h; Heating;	97%

7b,8-dihydro benzo[b]fluoranthene → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	92%

2-(phenanthren-9-yl)phenyl trifluoromethanesulfonate (146746-36-3) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl-formamide at 140℃; for 10h;	85%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 135 - 140℃; for 6h;	85%

9-((2-bromophenyl)methyl)-9H-fluorene (187754-47-8) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
Stage #1: 9-((2-bromophenyl)methyl)-9H-fluorene With potassium carbonate; 1,2-bis-(diphenylphosphino)ethane; palladium diacetate In N,N-dimethyl acetamide at 80℃; for 25h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 16h; Heating; Further stages.;	85%
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 48h;	52%

Z-1-(9'-phenanthyl)hexa-3-ene-1,5-diyne → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With 2,6-lutidine N-oxide; [BrettPhosAu]NTf2 In 1,2-dichloro-ethane at 20 - 80℃; for 24h; Molecular sieve;	80%

2-(phenanthrene-9-yl)aniline → benzo[e]acephenanthrylene (205-99-2) + 9-phenylphenanthrene (844-20-2)

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 20℃; for 10h; Concentration; Solvent; Reagent/catalyst;	A 80% B 6%

3,3a-dihydrobenzofluoranthene (88746-54-7) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.166667h; Heating;	79%

9-iodo-10-phenylphenanthrene (312612-61-6) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 110℃; for 48h;	78%

9-iodo-10-phenylphenanthrene (312612-61-6) → benzo[e]acephenanthrylene (205-99-2) + 9-phenylphenanthrene (844-20-2)

Conditions	Yield
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 110℃; for 48h;	A 78% B 18 % Chromat.

2-(phenanthrene-9-yl)aniline + phenylacetylene (536-74-3) → benzo[e]acephenanthrylene (205-99-2) + 9-phenylphenanthrene (844-20-2)

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation;	A 72% B 8%

9-(2-bromobenzylidene)fluorene (1643-48-7) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide	44%

1,8-dibromophenanthrene (20342-96-5) + (2-bromophenyl)boronic acid (244205-40-1) → benzo[e]acephenanthrylene (205-99-2) + benzindeno<1,2,3-hi>acephenanthrylene (340-19-2)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In N,N-dimethyl-formamide at 155℃; for 36h; Suzuki coupling, Heck coupling;	A 27% B 27%

9,10,11,12-tetrahydro-benz[e]acephenanthrylene (68597-14-8) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With selenium at 350℃;

9-(2-chlorobenzylidene)-9H-fluorene (1643-49-8) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With quinoline; potassium hydroxide
With potassium hydroxide; N,N-dimethyl-aniline

9-(2-chlorobenzyl)-9H-fluorene (861320-74-3) → benzo[e]acephenanthrylene (205-99-2)

Conditions	Yield
With quinoline; potassium hydroxide
With potassium hydroxide; N,N-dimethyl-aniline

Upstream product

• 68597-14-8 9,10,11,12-tetrahydro-benz[e]acephenanthrylene 
• 1643-49-8 9-(2-chlorobenzylidene)-9H-fluorene 
• 861320-74-3 9-(2-chlorobenzyl)-9H-fluorene 
• 243-17-4 2,3-benzofluorene 
• 1611-78-5 1,3-bis-dimethylaminotrimethinium perchlorate 
• 73129-94-9 2-(phenanthren-9-yl)cyclohexanone 
• 85-01-8 phenanthrene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 107010-20-8 tetrahydrobenzacephenanthrylene 
• 1643-48-7 9-(2-bromobenzylidene)fluorene 
• 91-22-5 quinoline 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 112575-96-9 2-(9-oxo-fluoren-1-yl)-benzoic acid 
• 112575-95-8 1-(2-Hydroxymethyl-phenyl)-9H-fluorene-2,9-diol 
• 57393-22-3 2-(9-Oxo-9H-fluoren-1-yl)-benzaldehyde 

Relevant academic research and scientific papers

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Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), potentially electronically and biologically highly active materials, were synthesized from readily available 2-aryl-substituted anilines. Reactions occur under extremely mild, room temperature conditions using tBuONO as the sole reagent. The use of a nitrite source generates a reactive diazonium intermediate in situ that then reacts with a tethered polycyclic aromatic moiety by intramolecular aromatic substitution. This protocol could be presented as one of the simplest methods to access CP-PAHs.

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Bidentate phosphines as ligands in the palladium-catalyzed intramolecular arylation: the intermolecular base-assisted proton abstraction mechanism

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Role of temperature and hydrochloric acid on the formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons during combustion of paraffin powder, polymers, and newspaper

Formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons (PAHs) were determined using a laboratory-scale incinerator when combusting materials at different temperatures, different concentrations of hydrochloric acid (HCl), and when combusting various types of polymers/newspaper. Polychlorobenzenes (PCBz), polychlorophenols (PCPhs), polychlorinated dibenzo-p-dioxins/furans (PCDD/Fs) and their toxic equivalency (TEQ) and PAHs were highlighted and reported. Our results imply maximum formation of chlorinated hydrocarbons at 400°C in the following order; PCBz≥PCPhs?PCDFs>PCDDs>TEQ on a parts-per-billion level. Similarly, a maximum concentration of chlorinated hydrocarbons was noticed with an HCl concentration at 1000 ppm with the presence of paraffin powder in the following order; PAHs>PCBz≥PCPhs?PCDFs>PCDDs>TEQ an a parts-per-billion level. PAHs were not measured at different temperatures. Elevated PAHs were noticed with different HCl concentrations and paraffin powder combustion (range: 27-32 μg/g). While, different polymers and newspaper combusted, nylon and acrylonitrile butadiene styrene (ABS) produced the maximum hydrogen cyanide (HCN) concentration, concentrations of PCDD/FS, dioxin-like polychlorinated biphenyls (DL-PCBs), and TEQ were in a decreasing order: polyvinylchloride (PVC)newspaperpolyethyleneterephthalate (PET) polyethylene (PE) polypropylene (PP) ABS = blank. Precursors of PCBs were in a decreasing order: PPnylonPEnewspaperABSPVCblankPET. Precursors of PCDD/Fs were in a decreasing order: newspaper PP= nylonPEABSPVC= blankPET. BTX formation was in a decreasing order; PEnylonnewspaperABSPP. PAHs formation were elevated with parts-per-million levels in the decreasing order of PPnylonPE newspaperblankABS PETPVC.

Emission factors and importance of PCDD/Fs, PCBs, PCNs, PAHs and PM 10 from the domestic burning of coal and wood in the U.K.

This paper presents emission factors (EFs) derived for a range of persistent organic pollutants (POPs) when coal and wood were subject to controlled burning experiments, designed to simulate domestic burning for space heating. A wide range of POPs were emitted, with emissions from coal being higher than those from wood. Highest EFs were obtained for particulate matter, PM10, (～ 10 g/kg fuel) and polycyclic aromatic hydrocarbons (～ 100 mg/ kg fuel for ΣPAHs). For chlorinated compounds, EFs were highest for polychlorinated biphenyls (PCBs), with polychlorinated naphthalenes (PCNs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) being less abundant. EFs were on the order of 1000 ng/kg fuel for ΣPCBs, 100s ng/ kg fuel for ΣPCNs and 100 ng/kg fuel for ΣPCDD/Fs. The study confirmed that mono- to trichlorinated dibenzofurans, Cl1,2,3DFs, were strong indicators of low temperature combustion processes, such as the domestic burning of coal and wood. It is concluded that numerous PCB and PCN congeners are routinely formed during the combustion of solid fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM 10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-ΣTEQ to total U.K. emissions was minor.

Experimental study on the removal of PAHs using in-duct activated carbon injection

This paper presents the incineration tests of municipal solid waste (MSW) in a fluidized bed and the adsorption of activated carbon (AC) on polycyclic aromatic hydrocarbons (PAHs). An extraction and high performance liquid chromatography (HPLC) technique was used to analyze the concentrations of the 16 US EPA specified PAHs contained in raw MSW, flue gas, fly ash, and bottom ash. The aim of this work was to decide the influence of AC on the distribution of PAHs during the incineration of MSW. Experimental researches show that there were a few PAHs in MSW and bottom ash. With the increase of AC feeding rate, the concentrations of three- to six-ring PAHs in fly ash increased, and the concentration of two-ring PAH decreased. The total-PAHs in flue gas were dominated by three-, and four-ring PAHs, but a few two-, five-ring PAHs and no six-ring PAHs were found. PAHs could be removed effectively from flue gas by using in-duct AC injection and the removal efficiencies of PAHs were about 76-91%. In addition, the total toxic equivalent (TEQ) concentrations of PAH in raw MSW, bottom ash, fly ash, and flue gas were 1.24 mg TEQ kg-1, 0.25 mg TEQ kg-1, 6.89-9.67 mg TEQ kg-1, and 0.36-1.50 μg TEQ N m-3, respectively.