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Usage

Uses

Used in Research and Development:
1,2:3,4-Dibenzanthracene is used as a research compound for studying the effects of PAHs on the environment and human health. Its application in this field is crucial for understanding the mechanisms of carcinogenicity and the development of strategies to mitigate the risks associated with PAH exposure.
Used in Environmental Monitoring:
As a known environmental pollutant, 1,2:3,4-dibenzanthracene is used as a marker compound in environmental monitoring and assessment. It helps in identifying contamination sources, tracking the spread of pollutants, and evaluating the effectiveness of remediation efforts.
Used in Industrial Applications:
Although 1,2:3,4-dibenzanthracene is a carcinogenic compound, it may still be used in specific industrial applications where its unique chemical properties are required. However, strict safety measures and regulations must be in place to minimize the risk of exposure and environmental contamination.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. Human mutation datareported. When heated to decomposition it emits acridsmoke and irritating fumes.

Carcinogenicity

Dibenz[a,c]anthracene was administered dermally to mice, either per se or as part of initiation–promotion protocols. The working group concluded that there was limited evidence for animal carcinogenicity. In later studies on an initiation–promotion study on mouse skin, low initiating doses gave negative results when administered subcutaneously to mice, and tumor incidence was not significantly increased over that observed in controls when the compound was administered intraperitoneally to newborn mice.

InChI:InChI=1/C22H14/c1-2-8-16-14-22-20-12-6-4-10-18(20)17-9-3-5-11-19(17)21(22)13-15(16)7-1/h1-14H

Upstream product

• 3228-74-8 dibenzanthracene-9,14-dione 
• 25486-89-9 10,11,12,13-tetrahydrodibenzanthracene 
• 77320-74-2 trans-5,6-Dihydroxy-5,6-divinyl-5,6-dihydrobenzanthracene 
• 100790-76-9 9,14-dihydro-9,14-epoxydibenzanthracene 
• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 93-09-4 naphthalene-2-carboxylate 
• 5411-56-3 1-(2-bromophenyl)ethanol 
• 2142-69-0 2-bromophenyl methyl ketone 
• 615-43-0 2-iodophenylamine 
• 71221-26-6 2-(2-naphthyl)aniline 
• 26767-16-8 2-(2-bromophenyl)-2-oxoacetic acid 
• 97295-35-7 2-(2-iodophenyl)naphthalene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 591-50-4 iodobenzene 

Downstream Products

• 83314-29-8 9-nitrodibenzanthracene 
• 25486-89-9 10,11,12,13-tetrahydrodibenzanthracene 
• 39081-15-7 10-hydroxydibenz[a,c]anthracene 

Relevant academic research and scientific papers

Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene

A new synthesis of dibenzo[a,c]anthracene (4) is described that features the generation, from tetrabromo-bis-triflate 1 and phenyllithium, of a 1,3,6-naphthotriyne (2) synthetic equivalent that is trapped with 3 equiv of furan to form Diels-Alder tris-adduct 3. A subsequent two-step deoxygenation of 3 represents the first synthesis of dibenz[a,c]anthracene (4) that involves a tandem aryne Diels-Alder cycloaddition-deoxygenation strategy.

Palladium Catalyzed C-I and Vicinal C-H Dual Activation of Diaryliodonium Salts for Diarylations: Synthesis of Triphenylenes

Using the synthetic strategy of palladium-catalyzed dual activation of both C-I and vicinal C-H bonds of diaryliodonium salts, we report an approach for direct diarylations of 2-bromobiphenyls or bromobenzenes. As a result, a wide range of triphenylenes with various substituents have been synthesized in good yields. These triphenylenes are expected to be employed in the "bottom-up" synthesis of functional aromatic molecules in material science.

Synthesis and characterization of oxadisilole fused benzo[b]triphenylene

Palladium-catalyzed [2+2+2] cyclotrimerization reactions between benzyne and oxadisilole fused oxabicyclic alkenes afforded the exo-adducts. Deoxygenation with BF3·OMe2 yielded mono- and bis-oxadisilole fused benzo[b]triphenylene. The photophysical properties of the oxadisilole fused benzo[b]triphenylenes were characterized.

Palladium-catalyzed [2 + 2 + 2] cocyclotrimerization of benzynes with bicyclic alkenes: An efficient route to anellated 9,10-dihydrophenanthrene derivatives and polyaromatic compounds

An efficient method for the cocyclotrimerization of bicyclic alkenes and benzynes catalyzed by palladium phosphine complexes to give the corresponding norbornane anellated 9,10-dihydrophenanthrene derivatives is described. Bicyclic alkenes 1a-i undergo [2 + 2 + 2] cocyclotrimerization with benzynes generated from precursors 2a-d [2-(trimethylsilyl)phenyl triflate (2a), 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate (2b), 6-(trimethylsilyl)-2,3- dihydro-1H-5-indenyl triflate (2c), 4-methyl-2-(trimethylsilyl)phenyl triflate (2d)] in the presence of PdCl2(PPh3)2 in acetonitrile at ambient temperature to yield anellated 9,10-dihydrophenanthrene products 3a-r in moderate to excellent yields. The [2 + 2 + 2] cocyclotrimerization products from oxa- and azabicyclic alkenes can be applied for the synthesis of polyaromatics, substituted benzo[b]triphenylenes (8a-f), via a simple Lewis acid mediated deoxyaromatization in good yields. In addition the [2 + 2 + 2] products undergo retro Diels-Alder reaction readily, providing a new method for the synthesis of substituted phenanthrenes and for generating isobenzofurans. A plausible mechanism is proposed to account for the catalytic [2 + 2 + 2] cycloaddition reaction.

Aluminium-mediated aromatic C-F bond activation: Regioswitchable construction of benzene-fused triphenylene frameworks

Selective synthesis of benzo[f]tetraphenes or benzo[g]chrysenes was achieved via aromatic C-F bond cleavage and unprecedented regioselective C-C bond formation depending upon the choice of aluminium reagents. On treatment with AlCl3, 2-(bipheny

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts

We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.

Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp2)-H Arylation, Cyclization, and Migration Tandem Reaction

Phenanthrene is an important structural motif in chemistry and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized with good to excellent yields.

Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation

A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.

Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes

Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.