67102-98-1

Usage

Molecular Structure

Complex and intricate, containing multiple bromine and chlorine atoms

Group

Polychlorinated biphenyls (PCBs)

Persistence

Known for their persistence in the environment

Bioaccumulation

Tends to accumulate in living organisms

Health Effects

Can have harmful effects on human and ecological health

Production and Use

Banned from production and use in many countries due to its harmful properties

Environmental Concern

A significant concern for environmental and human health due to its chemical structure and properties

Halogen Content

Contains bromine and chlorine atoms

Hydrocarbon Structure

Has a hydrocarbon structure with multiple chlorinated and brominated sites

Physical State

Likely a solid at room temperature, based on its molecular weight and complexity

Solubility

Likely insoluble in water due to its hydrophobic nature, but soluble in nonpolar organic solvents

Stability

Relatively stable due to its molecular structure, which contributes to its persistence in the environment

Toxicity

Potentially toxic due to its PCB classification and known harmful effects on human and ecological health

Applications

Historically used in various industrial applications, but now banned due to environmental and health concerns

Upstream product

• 80789-65-7 10-bromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene 
• 5696-92-4 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8dimethano-triphenylene 

Downstream Products

• 22187-13-9 1,4-dihydro-1,4-epoxyanthracene 
• 92-24-0 Tetracen 
• 120-12-7 anthracene 
• 13214-70-5 2,3-dibromonaphthalene 

Relevant academic research and scientific papers

Synthesis of substituted dibenz[a,c]anthracenes and an investigation of their liquid-crystalline properties

We report the synthesis of a series of 2,3,5,6-tetraalkoxydibenz[ a,c]anthracenes bearing substituents (H, OCH3, or CN) in the 11- and 12-positions and an investigation of their liquid- crystalline properties. The synthesis involved Suzuki coupling of the appropriate dibromonaphthalene and boronate ester, followed by an oxidative cyclization. Compounds 4 and 5, bearing OCH3 and H, respectively, do not exhibit any liquid-crystalline properties. In contrast, compounds 6a-c, bearing cyano groups, assemble into columnar mesophases, suggesting that electron-withdrawing groups are important for promoting columnar mesophase assembly. Analysis of the XRD revealed that compound 6b exhibits a columnar hexagonal phase, whereas compounds 6a and 6c exhibit columnar rectangular phases. The XRD data of 6a and 6b also show reflections that are consistent with antiparallel dimers within the columnar stacks, and intercolumnar spacings suggest that molecules are tilted within the columns.

A Convenient Generation of 2,3-Naphthalyne. Linear Annulation of Naphthalene and a New Naphthacene Synthesis

2,3-Naphthalyne (3) is conveniently generated by treating 2,3-dibromonaphthalene (9) with phenyllithium and is used in a two-step sequence to prepare naphthacene (1) and 1,2,3,4-tetrafluoronaphthacene (17).Thus, the cycloadditions of 3 with 2-methylisoindole (13) and 2-methyl-4,5,6,7-tetrafluoroisoindole (14) afford the naphthacenimines 15 and 16, respectively.Deamination with m-chloroperbenzoic acid (for 15) and dichlorocarbene (for 16) affords 1 and 17 in 44percent and 63percent overall yield from 9, respectively.Similarly, cycloadditions of 3 with furan and N-tert-butylpyrrole give anthracene, after extrusion of the heteroatom bridge.