207-08-9 Usage
Description
Synonyms for benzo(k)fluoranthene (BkF) include 8,9-benzfluoranthene, 8,9-benzofluoranthene, 1 1.12-benzofiuoranthene, 2,3,1,8-binaphthylene and dibenzo(bjk)fluorene. Its molecular weight is 252.32 and molecular formula C20H12. It is characterized by four benzene rings in various configurations containing only carbon and hydrogen atoms. It was absorbed through the skin, lungs, and gastrointestinal tract. In industrial processes it is considered to be environmental pollutants.
Clinical Trial
B(k)F is a weak carcinogen in mice and is also a weak tumor initiator. It is very much weaker than benzo(a)pyrene (BP). The observations regarding systemic tumors following topical application of these carcinogens to mice is of great importance. All too frequently, a dermal carcinogenicity study concentrates on skin tumors and no others. Thus, it is relatively unusual to have systemic tumors investigated. The fact that there was no difference in the level of systemic tumors in all groups, including the potent mouse carcinogen BP, would indicate that the level of systemic absorption through the skin was not significant.
Health Toxicity
B(k)F could penetrate the skin of some animals, especially mice, and remain present for a number of hours. The metabolism of B(k)F appears to follow a route leading to the predominant formation of its 5-hydroxy derivative. The further metabolism of this phenolic dihydrodiol to 5,9,10,trihydroxy-l1, 12-epoxy-9,10,11,12-tetrahydro- benzo(k)fluoranthene has been linked to the genotoxic effect of B(k)F in mouse skin. Care was taken to avoid contact with the head, axillae, and genital areas.
Chemical Properties
yellow crystals
Uses
Benzo[k]fluoranthene is used as an optical sensor for nitro-aromatic compounds due to fluorescence quenching of the molecule. It is also a carcinogen and mutagen.
General Description
Pale yellow needles or yellow crystalline solid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
BENZO[K]FLUORANTHENE can react with strong oxidizing agents. May react with electrophiles, peroxides, nitrogen oxides and sulfur oxides
Hazard
Possible carcinogen.
Health Hazard
Different sources of media describe the Health Hazard of 207-08-9 differently. You can refer to the following data:
1. Benzo[k]fluoranthene caused lungs and skincancers in animals. It produced tumors atthe site of application. Its carcinogenicity inhumans is not known.
2. ACUTE/CHRONIC HAZARDS: When heated to decomposition BENZO(K)FLUORANTHENE emits acrid smoke and irritating fumes.
Fire Hazard
Flash point data for BENZO(K)FLUORANTHENE are not available; however, BENZO(K)FLUORANTHENE is probably combustible.
Safety Profile
Confirmed carcinogen withexperimental tumorigenic data. Mutation data reported.When heated to decomposition it emits acrid smoke andirritating fumes.
Carcinogenicity
Benzo[k]fluoranthenewastested
for carcinogenicity by dermal application in mice in one
study, intraperitoneal injection into newborn mice
in one study, and intrapulmonary implantation into
rats in one study. Benzo[k]fluoranthene exhibited a
significant carcinogenic activity in the dermal and intrapulmonary
assays.
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 gasoline (9 μg/L), bitumen (34–1,140 μg/L), crude oil (<1 ppm)
(quoted, Verschueren, 1983), and coal (32.5 g/kg) (Lao et al., 1975).
Based on laboratory analysis of 7 coal tar samples, benzo[k]fluoranthene concentrations ranged
from 350 to 3,000 ppm (EPRI, 1990). Identified in high-temperature coal tar pitches used in
roofing operations at concentrations ranging from 1,670 to 4,500 mg/kg (Malaiyandi et al., 1982).
Nine commercially available creosote samples contained benzo[k]fluoranthene at concentrations
ranging from 2 to 67 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[k]fluoranthene were 0.671 mg/kg of pine burned, 0.303 mg/kg of oak
burned, and 0.286 mg/kg of eucalyptus burned.
California Phase II reformulated gasoline contained benzo[k]fluoranthene at a concentration of
280 μg/kg. Particle-phase tailpipe emission rate from a noncatalyst-equipped gasoline-powered
automobile was 32.7 μg/km (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[k]fluoranthene emitted ranged from 0 ng/kg at three temperatures (650, 750, and
950 °C) to 180.5 ng/kg at 850 °C. The greatest amount of PAHs emitted were observed at 750 °C
(Mastral et al., 1999).
Environmental fate
Soil. Based on aerobic soil die-away test data, the half-life in soil ranged from 910 d to 5.86 yr
(Bossert et al., 1984).
Photolytic. The atmospheric half-life was estimated to range from 1.1 to 11 h (Atkinson, 1987).
Chemical/Physical. Benzo[k]fluoranthene will not hydrolyze because it has no hydrolyzable
functional group (Kollig, 1995).
Check Digit Verification of cas no
The CAS Registry Mumber 207-08-9 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 7 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 207-08:
(5*2)+(4*0)+(3*7)+(2*0)+(1*8)=39
39 % 10 = 9
So 207-08-9 is a valid CAS Registry Number.
InChI:InChI=1S/C20H12/c1-2-6-15-12-19-17-10-4-8-13-7-3-9-16(20(13)17)18(19)11-14(15)5-1/h1-12H
207-08-9Relevant articles and documents
Exploring the chemistry of a double-stranded cycle with the carbon skeleton of the belt region of the C84 fullerene
Stuparu, Mihaiela,Lentz, Dieter,Rueegger, Heinz,Schlueter, A. Dieter
, p. 88 - 100 (2007)
Intense scale-up efforts greatly improved the availability of the known double-stranded cycle 2 with two bridging ether units. The chemistry of 2 towards Bronsted and Lewis acids could, therefore, be investigated quite comprehensively. It was discovered that the reactivity of 2, whose carbon framework resembles the belt region of the C84 (D2) fullerene, is rather unusual as compared with acyclic model compounds. Whereas the latter could easily be dehydrated to the corresponding planar arenes, the former gave rise to a bouquet of unexpected reactions, which all avoided the aromatization of 2 to its still-elusive, fully conjugated congener B. Intermediates generated from 2 under acidic conditions attack the solvent (e.g. toluene) to give 4, form bridging lactones to give 11 or close back to starting material 2 (e.g. from 16) rather than dehydrate to more highly conjugated structures on the way to the fully unsaturated target cycle B. The structure of compound 4 was solved by X-ray diffraction. Through the reactions of 2 with Lewis acids, derivatives 14 and 15 became accessible. They are candidates for future attempts to achieve the desired aromatization under basic conditions or by thermal treatment. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Whitlock
, p. 3129 (1964)
Scholl Cyclizations of Aryl Naphthalenes: Rearrangement Precedes Cyclization
Skraba-Joiner, Sarah L.,McLaughlin, Erin C.,Ajaz, Aida,Thamatam, Rajesh,Johnson, Richard P.
, p. 9578 - 9583 (2015/10/12)
In 1910, Scholl, Seer, and Weitzenbock reported the AlCl3-catalyzed cyclization of 1,1′-binaphthyl to perylene. We provide evidence that this classic organic name reaction proceeds through sequential and reversible formation of 1,2′- and 2,2′-binaphthyl isomers. Acid-catalyzed isomerization of 1,1′-binaphthyl to 2,2′-binaphthyl has been noted previously. The superacid trifluoromethanesulfonic acid (TfOH), 1 M in dichloroethane, catalyzes these rearrangements, with slower cyclization to perylene. Minor cyclization products are benzo[k]fluoranthene and benzo[j]fluoranthene. At ambient temperature, the observed equilibrium ratio of 1,1′-binaphthyl, 1,2′-binaphthyl, and 2,2′-binaphthyl is 1:3:97. DFT calculations with the inclusion of solvation support a mechanistic scheme in which ipso-arenium ions are responsible for rearrangements; however, we cannot distinguish between arenium ion and radical cation mechanisms for the cyclization steps. Under similar reaction conditions, 1-phenylnaphthalene interconverts with 2-phenylnaphthalene, with the latter favored at equilibrium (5:95 ratio), and also converts slowly to fluoranthene. Computations again support an arenium ion mechanism for rearrangements.
Role of temperature and hydrochloric acid on the formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons during combustion of paraffin powder, polymers, and newspaper
Takasuga, Takumi,Umetsu, Norihito,Makino, Tetsuya,Tsubota, Katsuya,Sajwan, Kenneth S.,Kumar, Kurunthachalam Senthil
, p. 8 - 21 (2008/02/09)
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.
