206-44-0 Usage
Uses
Used in Conducting Polymer Synthesis:
Fluoranthene is used as a starting material for the synthesis of polyfluoranthene (PFA) based conducting polymer (PFA) by electrochemical anodic oxidation using Lewis acid catalyst.
Used in Substituted Fluorenone Synthesis:
Fluoranthene is used as a starting material for the synthesis of substituted fluorenones.
Used in Fluorescence-Emitting Oligofluoranthene Nanorods Synthesis:
Fluoranthene is used as a starting material for the synthesis of fluorescence-emitting oligofluoranthene (OFA) nanorods by oxidative oligomerization.
Synthesis Reference(s)
Journal of the American Chemical Society, 72, p. 4786, 1950 DOI: 10.1021/ja01166a124Tetrahedron Letters, 33, p. 1675, 1992 DOI: 10.1016/S0040-4039(00)91703-9
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Fluoranthene, and strong oxidizing agents. They 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
Questionable carcinogen.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition Fluoranthene emits acrid smoke and fumes.
Health Hazard
Fluoranthene exhibited mild oral and dermaltoxicity in animals. The acute toxicity is lowerthan that of phenanthrene. An oral LD50 valuein rats is reported as 2000 mg/kg. It may causeskin tumor at the site of application. However,any carcinogenic action from this compoundin animals is unknown..
Fire Hazard
Flash point data for Fluoranthene are not available. Fluoranthene is probably combustible.
Safety Profile
Poison by intravenous
route. Moderately toxic by ingestion and
skin contact. Questionable carcinogen with
experimental tumorigenic data. Human
mutation data reported. Combustible when
exposed to heat or flame. When heated to
decomposition it emits acrid smoke and irritating fumes.
Potential Exposure
Fluoranthene, a PAH, is produced
from the pyrolytic processing of organic raw materials,
such as coal and petroleum at high temperatures. It is also
known to occur naturally as a product of plant biosynthesis.
Fluoranthene is ubiquitous in the environment and has been
detected in United States air; in foreign and domestic drink ing waters and in food-stuffs. It is also contained in ciga rette smoke. Individuals living in areas which are heavily
industrialized; and in which large amounts of fossil fuels
are burned, would be expected to have greatest exposure
from ambient sources of fluoranthene. In addition, certain
occupations e.g., coke oven workers, steelworkers, roofers,
automobile mechanics) would also be expected to have elevated levels of exposure relative to the general popula tion. Exposure to fluoranthene will be considerably
increased among tobacco smokers or those who are
exposed to smokers in closed environments (i.e., indoors).
Source
Detected in 8 diesel fuels at concentrations ranging from 0.060 to 13 mg/L with a mean
value of 0.113 mg/L (Westerholm and Li, 1994); in a distilled water-soluble fraction of used
motor oil at a concentration range of 1.3 to 1.5 μg/L (Chen et al., 1994). Lee et al. (1992) reported
concentration ranges 1.50-125 mg/L and ND-0.5 μg/L in diesel fuel and the corresponding
aqueous phase (distilled water), respectively (Lee et al., 1992). Schauer et al. (1999) reported
fluoranthene in a diesel-powered medium-duty truck exhaust at an emission rate of 53.0 μg/km.
Identified in Kuwait and South Louisiana crude oils at concentrations of 2.9 and 5.0 ppm,
respectively (Pancirov and Brown, 1975).
California Phase II reformulated gasoline contained fluoranthene at a concentration of 1.15
g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were approximately 4.25 and 160 μg/km, respectively (Schauer et al., 2002).
Detected in groundwater beneath a former coal gasification plant in Seattle, WA at a
concentration of 50 μg/L (ASTR, 1995). The concentration of fluoranthene in coal tar and the
maximum concentration reported in groundwater at a mid-Atlantic coal tar site were 6,500 and
0.015 mg/L, respectively (Mackay and Gschwend, 2001). Based on laboratory analysis of 7 coal
tar samples, fluoranthene concentrations ranged from 1,500 to 13,000 ppm (EPRI, 1990).Lehmann et al. (1984) reported fluoranthene concentrations of 64.7 mg/g in a commercial
anthracene oil and 17,400 to 30,900 mg/kg in three high-temperature coal tars. Identified in hightemperature
coal tar pitches used in roofing operations at concentrations ranging from 5,200 to
38,800 mg/kg (Arrendale and Rogers, 1981).
Fluoranthene was detected in soot generated from underventilated combustion of natural gas
doped with toluene (3 mole %) (Tolocka and Miller, 1995). Fluoranthene was also detected in 9
commercially available creosote samples at concentrations ranging from 55,000 to 120,000 mg/kg
(Kohler et al., 2000).
Detected in asphalt fumes at an average concentration of 20.48 ng/m3 (Wang et al., 2001).
An impurity in commercial available pyrene (Marciniak, 2002).
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 respective gas-phase
and particle-phase emission rates of fluoranthene were 3.05 and 3.95 mg/kg of pine burned, 3.61
and 1.20 mg/kg of oak burned, and 3.75 and 0.509 mg/kg of eucalyptus burned.
Solubility in organics
In benzene expressed as mole fraction: 0.2174 at 44.8 °C, 0.3011 at 56.0 °C, 0.3826 at 64.4 °C,
0.5331 at 77.2 °C (shake flask-gravimetric, McLaughlin and Zainal, 1959)
In millimole fraction at 25 °C: 14.76 in n-hexane, 18.70 in n-heptane, 22.60 in n-octane, 26.42 in
n-nonane, 30.15 in n-decane, 50.46 in n-hexadecane, 18.07 in cyclohexane, 21.79 in methylcyclohexane,
30.11 in cyclooctane, 11.62 in 2,2,4-trimethylpentane, 24.82 in tert-butyl-cyclohexane,
51.77 in dibutyl ether, 47.55 in methyl tert-butyl ether, 2.67 in methanol, 5.44 in
ethanol, 6.70 in 1-propanol, 4.75 in 2-propanol, 9.96 in 1-butanol, 7.02 in 2-butanol, 4.95 in 2-
methyl-1-propanol, 14.46 in 1-pentanol, 19.86 1-hexanol, 25.24 in 1-heptanol, 31.25 in 1-
octanol, 10.21 in 2-pentanol, 8.62 in 3-methyl-1-butanol, 9.70 in 2-methyl-2-butanol, 17.72 in
cyclopentanol, 17.82 in 2-ethyl-1-hexanol, 11.72 in 2-methyl-1-pentanol, 0.948 in 4-methyl-2-
pentanol (Hernández and Acree, 1998)
Shipping
UN1325 Flammable solids, organic, n.o.s.,
Hazard Class: 4.1; Labels: 4.1-Flammable solid.UN3077
Environmentally hazardous substances, solid, n.o.s., Hazard
class: 9; Labels: 9-Miscellaneous hazardous material,
Technical Name Required.
Purification Methods
Fluoranthene (benzo[j,k]fluorene) M 202.3, m 110-111o, b 384o/760mm. Purify it by chromatography of CCl4 solutions on alumina, with *benzene as eluent. Crystallise it from EtOH, MeOH or *benzene. Also purify it by zone melting. [Gorman et al. J Am Chem Soc 107 4404 1985, Beilstein 5 I 344, 5 IV 2463.]
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Compound can react exo thermically with bases and with diazo compounds.
Substitution at the benzene nucleus occurs by halogenation
(acid catalyst), nitration, sulfonation, and the Friedel Crafts reaction.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. Consult with environmental regulatory agencies
for guidance on acceptable disposal practices. Generators of
waste containing this contaminant (≥100 kg/mo) must con form with EPA regulations governing storage, transportation,
treatment, and waste disposal.
Check Digit Verification of cas no
The CAS Registry Mumber 206-44-0 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 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 206-44:
(5*2)+(4*0)+(3*6)+(2*4)+(1*4)=40
40 % 10 = 0
So 206-44-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H
206-44-0Relevant articles and documents
Bicyclohexene- peri-naphthalenes: Scalable Synthesis, Diverse Functionalization, Efficient Polymerization, and Facile Mechanoactivation of Their Polymers
Yang, Jinghui,Horst, Matias,Werby, Sabrina H.,Cegelski, Lynette,Burns, Noah Z.,Xia, Yan
, p. 14619 - 14626 (2020)
Pursuing polymers that can transform from a nonconjugated to a conjugated state under mechanical stress to significantly change their properties, we developed a new generation of ladder-type mechanophore monomers, bicyclo[2.2.0]hex-5-ene-peri-naphthalene (BCH-Naph), that can be directly and efficiently polymerized by ring-opening metathesis polymerization (ROMP). BCH-Naphs can be synthesized in multigram quantities and functionalized with a wide range of electron-rich and electron-poor substituents, allowing tuning of the optoelectronic and physical properties of mechanically generated conjugated polymers. Efficient ROMP of BCH-Naphs yielded ultrahigh molecular weight polymechanophores with controlled MWs and low dispersity. The resulting poly(BCH-Naph)s can be mechanically activated into conjugated polymers using ultrasonication, grinding, and even simple stirring of the dilute solutions, leading to changes in absorption and fluorescence. Poly(BCH-Naph)s represent an attractive polymechanophore system to explore multifaceted mechanical response in solution and solid states, owing to the synthetic scalability, functional diversity, efficient polymerization, and facile mechanoactivation.
A Microsynthesis of Fluoranthene
Maly, Ernest
, p. 1103 - 1104 (1981)
A simple synthesis of fluoranthene based on the distillation of benzanthrone with zinc dust is described, in addition to those cited in Clar's monograph.It may be useful for small scale preparations of this polycyclic hydrocarbon.The pure product was obtained by chromatography. - Keywords: Polycyclic hydrocarbon; Zinc dust distillation
Novel and rapid palladium-assisted 6π electrocyclic reaction affording 9,10-dihydrophenanthrene and its analogues
Jana, Rathin,Chatterjee, Indranil,Samanta, Shubhankar,Ray, Jayanta K.
, p. 4795 - 4797 (2008)
(Equation Presented) A novel methodology for the synthesis of 9,10-dihydrophenanthrene and its analogues has been developed via a palladium-assisted 6π electrocyclic reaction followed by formaldehyde elimination.
Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes
Gonzalez, Juan J.,Francesch, Andres,Cardenas, Diego J.,Echavarren, Antonio M.
, p. 2854 - 2857 (1998)
The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.
Phenyl migrations in dehydroaromatic compounds. A new mechanistic link between alternant and nonalternant hydrocarbons at high temperatures
Preda, Dorin V.,Scott, Lawrence T.
, p. 1489 - 1492 (2000)
(Matrix presented) Flash vacuum pyrolysis of benzo[b]biphenylene, an alternant polycyclic aromatic hydrocarbon (PAH), gives fluoranthene, a nonalternant PAH, as the major product at 1100 °C in the gas phase. The most reasonable mechanism to explain this isomerization involves equilibrating diradicals of 2-phenylnaphthalene that rearrange by the net migration of a phenyl group to give equilibrating diradicals of 1-phenylnaphthalene, one isomer of which then cyclizes to fluoranthene.
Tellurium-Mediated Cycloaromatization of Acyclic Enediynes under Mild Conditions
Landis, Chad A.,Payne, Marcia M.,Eaton, David L.,Anthony, John E.
, p. 1338 - 1339 (2004)
The cycloaromatization of acyclic enediynes typically requires very high temperatures (>160 °C) and dilute conditions to proceed in a synthetically useful yield. These conditions hinder reaction throughput, inhibiting the use of this reaction for the large-scale production of materials. The reaction of sodium telluride with acyclic arenediynes yields the corresponding tellurepine, which under gentle heating extrudes Te° to yield the cycloaromatization product. We have developed conditions that form sodium telluride from inexpensive tellurium metal in situ, and that also perform the desilylation of silylated arenediynes in the same process. Under our conditions, we are able to perform desilylation and cycloaromatization at temperatures as low as 40 °C and on a scale as large as 5 g in standard laboratory glassware. Copyright
Mechanisms of Heptane Degradation and Product Formation in Microwave Discharge
Bobkova,Stokolos,Garifullin
, p. 336 - 340 (2019/08/15)
Abstract: A mechanism for the degradation of n-heptane and the formation of the products of its plasma-chemical transformation by microwave discharge treatment has been proposed. Chemical reactions resulting in reactive species, namely free radicals that form lower hydrocarbons and polyaromatic structures are presented. The product composition of the gas, liquid, and solid phases has been studied using gas chromatography–mass spectrometry analysis of the precipitate obtained by evaporation of the liquid phase after the treatment of n-heptane.
Pd-Catalyzed Annulation of 1-Halo-8-arylnaphthalenes and Alkynes Leading to Heptagon-Embedded Aromatic Systems
Yan, Jianming,Rahman, Md. Shafiqur,Yoshikai, Naohiko
, p. 9395 - 9399 (2019/01/04)
A palladium-catalyzed heptagon-forming annulation reaction between 1-halo-8-arylnaphthalene and diarylacetylene is reported. The reaction is promoted using a catalytic system comprised of Pd(OAc)2, moderately electron-deficient triarylphosphine P(4-ClC6H4)3, and Ag2CO3 to afford benzo[4,5]cyclohepta[1,2,3-de]naphthalene derivatives in moderate to good yields, in preference to fluoranthene as a competing byproduct. Twofold annulation can also be achieved to access a novel heptagon-embedded polycyclic aromatic hydrocarbon compound.
Intramolecular Remote C-H Activation via Sequential 1,4-Palladium Migration to Access Fused Polycycles
Li, Panpan,Li, Qiuyu,Weng, He,Diao, Jiaming,Yao, Hequan,Lin, Aijun
supporting information, p. 6765 - 6769 (2019/09/07)
An unprecedented intramolecular remote C-H activation via sequential 1,4-palladium migration with an aromatic ring as a conveyor has been described. This reaction provides an efficient route to construct diverse polycyclic frameworks in moderate to good yield via palladium-catalyzed remote C-H activation/alkene insertion, arylation, alkenylation, and the Heck reaction. The preliminary mechanistic studies revealed that the 1,4-palladium migration process was reversible.
Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way
Zhao, Long,Prendergast, Matthew B.,Kaiser, Ralf I.,Xu, Bo,Ablikim, Utuq,Ahmed, Musahid,Sun, Bing-Jian,Chen, Yue-Lin,Chang, Agnes H. H.,Mohamed, Rana K.,Fischer, Felix R.
supporting information, p. 17442 - 17450 (2019/11/11)
Polycyclic aromatic hydrocarbons (PAHs) represent the link between resonance-stabilized free radicals and carbonaceous nanoparticles generated in incomplete combustion processes and in circumstellar envelopes of carbon rich asymptotic giant branch (AGB) stars. Although these PAHs resemble building blocks of complex carbonaceous nanostructures, their fundamental formation mechanisms have remained elusive. By exploring these reaction mechanisms of the phenyl radical with biphenyl/naphthalene theoretically and experimentally, we provide compelling evidence on a novel phenyl-addition/dehydrocyclization (PAC) pathway leading to prototype PAHs: triphenylene and fluoranthene. PAC operates efficiently at high temperatures leading through rapid molecular mass growth processes to complex aromatic structures, which are difficult to synthesize by traditional pathways such as hydrogen-abstraction/acetylene-addition. The elucidation of the fundamental reactions leading to PAHs is necessary to facilitate an understanding of the origin and evolution of the molecular universe and of carbon in our galaxy.
