2,6-Dibromoanthracene
[CAS# 186517-01-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: 2,6-Dibromoanthracene
• Molecular Formula: C₁₄H₈Br₂
• Molecular Weight: 336.02
• CAS Registry Number: 186517-01-1
• SMILES: C1=CC(=CC2=CC3=C(C=C21)C=C(C=C3)Br)Br

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.749, Calc.^*
• Boiling Point: 438.8±18.0 °C (760 mmHg), Calc.^*
• Flash Point: 256.2±20.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

2,6-Dibromoanthracene is a chemical compound that belongs to the class of anthracene derivatives, which are widely studied for their optical and electronic properties. The compound consists of an anthracene backbone, a polycyclic aromatic hydrocarbon, with bromine atoms attached to the 2 and 6 positions of the benzene rings. This substitution pattern influences the molecule's chemical reactivity and physical properties, making it a valuable intermediate in organic synthesis and a compound of interest for various industrial applications.

The discovery of 2,6-dibromoanthracene can be traced back to the ongoing exploration of brominated polycyclic aromatic hydrocarbons, which are known for their ability to participate in a variety of reactions due to the electronegativity of the bromine atoms. The introduction of bromine atoms into the anthracene structure enhances its solubility in organic solvents and modifies its electronic properties, making it suitable for use in different chemical processes.

One of the primary applications of 2,6-dibromoanthracene is in organic electronics, particularly in the field of organic semiconductors. The compound has been investigated for use in the fabrication of organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The presence of bromine atoms in the structure is known to facilitate charge transfer and enhance the material’s ability to absorb and emit light, which is crucial for the efficiency of OLED devices. Organic semiconductors such as 2,6-dibromoanthracene are being developed as alternatives to traditional inorganic semiconductors due to their flexibility, low cost, and ease of processing.

In addition to its use in organic electronics, 2,6-dibromoanthracene is also employed as a precursor in the synthesis of other complex organic molecules. The bromine atoms attached to the anthracene ring make the compound highly reactive in cross-coupling reactions, such as the Suzuki and Heck reactions, which are widely used in organic synthesis to create carbon-carbon bonds. Through these reactions, 2,6-dibromoanthracene can be transformed into a variety of functionalized derivatives with diverse applications in materials science and drug development.

Moreover, 2,6-dibromoanthracene is studied for its potential biological activity. Brominated anthracene derivatives have been shown to possess antimicrobial, anticancer, and anti-inflammatory properties. Researchers are exploring the therapeutic potential of these compounds in drug development, particularly for the treatment of cancer and other diseases. The unique electronic structure of the molecule, as influenced by the bromine atoms, is thought to play a role in its bioactivity, making it a subject of ongoing pharmacological investigation.

Another area of application for 2,6-dibromoanthracene is in the development of sensors and detection systems. The compound’s ability to undergo selective reactions with other chemicals makes it useful in the design of devices that can detect specific molecules or ions. Its properties also make it suitable for use in analytical chemistry, where it can serve as a probe for studying chemical interactions and reaction mechanisms.

In summary, 2,6-dibromoanthracene is a versatile chemical compound with applications in organic electronics, materials science, and drug development. Its unique structural features, including the presence of bromine atoms, make it an important building block for a wide range of chemical processes and technologies. Ongoing research continues to explore its potential in various industries, from electronics to pharmaceuticals.

References

2021. Atmospheric deposition of chlorinated and brominated polycyclic aromatic hydrocarbons in central Europe analyzed by GC-MS/MS. Environmental Science and Pollution Research International.
DOI: 10.1007/s11356-021-15038-3

2010. X- and H-Shape Two Dimensional Conjugated Oligomers with Anthracene as the Node. Chemistry - An Asian Journal.
DOI: 10.1002/asia.200900591

2007. Synthesis and Thermal Characterization of Novel Poly(tetramethylsilanthrylenesiloxane) and Poly(tetramethylsilphenanthrylenesiloxane) Derivatives. Polymer Bulletin.
DOI: 10.1007/s00289-007-0804-7