203-12-3

Usage

Uses

Used in Analytical Chemistry:
BENZO(G,H,I)FLUORANTHENE is used as a chemical marker for the detection of carbon black mutagenicity. Its presence in samples can indicate the potential mutagenicity of carbon black, which is crucial for understanding the health and environmental implications of exposure to this substance.
Used in Research and Development:
Due to its unique chemical properties, BENZO(G,H,I)FLUORANTHENE is employed as a research compound in various scientific studies. It aids in the investigation of the properties and behavior of polycyclic aromatic hydrocarbons, which can contribute to the development of new materials and technologies.
Used in Industrial Applications:
BENZO(G,H,I)FLUORANTHENE may also find use in specific industrial applications where its chemical properties are advantageous. For instance, its fluorescence characteristics could be utilized in the development of certain types of sensors or imaging technologies.

Safety Profile

Mutation data reported.Questionable carcinogen. When heated to decompositionit emits acrid smoke and irritating vapors.

Carcinogenicity

Available data are inadequate to evaluate the carcinogenicity of benzo[ghi]fluoranthene in experimental animals.

InChI:InChI=1/C18H10/c1-3-11-7-9-13-10-8-12-4-2-6-15-14(5-1)16(11)18(13)17(12)15/h1-10H

Upstream product

• 74-85-1 ethene 
• 159418-51-6 1-chlorobenzo[c]phenanthrene 
• 25450-18-4 1,2,9,10,10a,10b-Hexahydro-benzo[ghi]fluoranthene 
• 195-19-7 benzo[c]phenathrene 
• 27208-37-3 cyclopenta[c,d]pyrene 
• 3074-00-8 naphthanthrone 
• 6709-40-6 benzo[c]phenanthrene-5,6-dicarboxylic acid-anhydride 
• 205-82-3 Benzo[j]fluoranthene 
• 53034-15-4 2-bromobenzophenanthrene 
• 24756-50-1 benzo<3,4>cyclobuta<1,2-b>biphenylene 
• 255871-44-4 4-(2'-carboxyethyl)-4H-cyclopenta[def]phenanthrene 
• 120-12-7 anthracene 
• 159418-31-2 1,3-Dichlorobenzo[c]phenanthrene 
• 159418-34-5 4-Bromo-1-chlorobenzo[c]phenanthrene 

Downstream Products

• 27208-37-3 cyclopenta[c,d]pyrene 

Relevant academic research and scientific papers

Synthesis of Benzofluoranthenes from 1-Halobenzophenanthrenes by Flash Vacuum Pyrolysis

1-Chlorobenzophenanthrene 23 was prepared via the oxidative photochemical cyclisation of suitably halogenated stilbenes and was cyclised to benzofluoranthene 2 by flash vacuum pyrolysis.

From phenylenes to acenes: Flash vacuum pyrolytic isomerization of angular [3]phenylene to benzo[ghi]fluoranthene

The flash vacuum pyrolysis of angular [3]phenylene and bis(2-ethynylphenyl)ethyne produces benzo[ghi]fluoranthene and chrysene, respectively.

Thermolysis of benzo[c]phenanthrene: Conversion of an alternant C18H12 PAH into non-alternant C18H10 PAHs

The product composition of the pyrolysates obtained upon thermolysis of the alternant C18H12 PAH benzo[c]phenanthrene (1) is markedly pressure dependent. At 0.1-0.5 Torr (N2 carrier gas, 1050-1150°C) 1 is converted into the non-alternant C18H10PAH's cyclopenta[cd]pyrene (4) and benzo[ghi]fluoranthene (5) which have been identified as abundant combustion effluents and are associated with fullerene formation.

Use of external radical sources in flash vacuum pyrolysis to facilitate cyclodehydrogenation reactions in polycyclic aromatic hydrocarbons

A new process to facilitate the cyclodehydrogenation of polycyclic aromatic hydrocarbons (PAHs) in flash vacuum pyrolysis (FVP) using an external radical source is described. Using hexanes as an external radical source the conversion of various PAHs to their cyclodehydrogenated products is vastly increased. Various other volatile organic compounds were also examined to determine their ability to act as external radical sources in FVP.

Intramolecular aryl-aryl coupling of fluoroarenes through Al 2O3-mediated HF elimination

A strategy for effective intramolecular aryl-aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C-F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C-C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.

Facile bucky-bowl synthesis by regiospecific cove-region closure by Hf elimination

Building bowls: An effective intramolecular aryl-aryl coupling is the key step in rational fullerene synthesis and in synthesis of extended buckybowl structures. Such a process can be embodied very efficiently through quantitative HF elimination on active Al2O3. The process is characterized by an unprecedentedly high chemoselectivity and regiospecificity. Copyright

Highly efficient fluorine-promoted intramolecular condensation of benzo[c]phenanthrene: A new prospective on direct fullerene synthesis

Various functional groups have been tested as alternative promoters of the intramolecular condensation of benzo-[c]phenanthrene under flash vacuum pyrolysis conditions. Methyl and fluorine functionalization were found to be promising approaches. Unexpectedly high selectivity was observed in the cyclization of fluorinated benzo[c]phenanthrenes. The mechanism for the condensation reaction and the advantages of fluorine as a promoter for the rational synthesis of fullerenes are discussed. Wiley-VCH Verlag GmbH & Co. KGaA.

Aryl-aryl bond formation by flash vacuum pyrolysis of benzannulated thiopyrans

(Chemical Equation Presented) In contrast to fully unsaturated 7-membered ring sulfur heterocycles (thiepines), some of which extrude sulfur and give the ring-contracted hydrocarbon even at room temperature in solution, benzannulated thiopyrans (6-membere

Interconversions of aryl radicals by 1,4-shifts of hydrogen atoms. A synthesis of benzo[a]corannulene

Aryl radicals generated ortho to aryl substituents by flash vacuum pyrolysis (FVP) of the corresponding aryl chlorides are shown to be capable of transferring hydrogen atoms between the ortho and ortho' positions (1,4-shifts of hydrogen atoms). In the examples described here, the rearranged aryl radicals are trapped by subsequent radical cyclization reactions. For example, FVP of 2-(ochlorophenyl)-benzo[c]phenanthrene gives 1-phenylbenzo[ghi]fluoranthene as the major product by homolysis of the C-CI bond, 1,4-shift of a hydrogen atom out of the sterically congested cove region to the radical center, cyclization of the rearranged radical, and rearomatization of the molecule by loss of the other cove region hydrogen. In a control experiment run under the same conditions, FVP of 2-phenylbenzo[c]phenanthrene, which lacks a radical precursor, gave primarily recovered starting material. When the FVP was repeated using 2-(2,6-dichlorophenyl)benzo[c]phenanthrene as the starting material, benzo[a]corannulene was obtained as the major product, presumably by the same cascade of events to produce 1-(o-chlorophenyl)benzo[ghi]-fluoranthene, which then suffers a second radical cyclization spontaneously under the high-temperature conditions to give the geodesic polyarene.

Isomerization of linear to angular [3]phenylene and PAHs under flash vacuum pyrolysis conditions

(matrix presented) Flash vacuum pyrolysis (FVP) of linear [3]phenylene affords its angular counterpart and the same mixture of polycyclic aromatic hydrocarbon isomers as that observed on FVP of angular [3]phenylene. A mechanism, supported by a 13C labeling study, is proposed to explain these results.