3,6-Dibromophenanthrene-9,10-dione: Properties & Uses FAQ

3,6-Dibromophenanthrene-9,10-dione is a brominated aromatic 1,2-diketone building block derived from the phenanthrene scaffold, widely employed as a reactive intermediate in the synthesis of advanced organic electronic materials, luminescent compounds, and functional heterocyclic frameworks.

IUPAC Name

3,6-Dibromophenanthrene-9,10-dione

SKU / Product Code

D290447

Core Functional Groups

Two carbonyl groups (1,2-diketone) and two aryl bromide substituents

Molecular Framework

Phenanthrene (tricyclic aromatic hydrocarbon) with 9,10-dione motif

Primary Application Area

Organic electronics, OLED materials, and heterocyclic synthesis

Reactivity Handles

Aryl C–Br bonds (cross-coupling) and electrophilic diketone carbonyls (condensation)

What Is 3,6-Dibromophenanthrene-9,10-dione?

3,6-Dibromophenanthrene-9,10-dione (Aladdin SKU: D290447) is an aromatic ortho-diketone built on the phenanthrene tricyclic framework. The two bromine substituents are located at the 3- and 6-positions of the aromatic ring system, while the vicinal dione (1,2-diketone) functionality occupies the 9- and 10-positions bridging the central ring. This combination of electron-withdrawing carbonyl groups and reactive aryl bromide handles makes the compound a highly versatile bifunctional building block.

The compound belongs to the phenanthrenequinone family, which has been extensively studied for its electron-accepting properties, photochemical reactivity, and role as a scaffold in extended π-conjugated systems used in organic semiconductors and luminescent materials.

Key Chemical Properties and Handling

Solubility: Phenanthrenequinone derivatives are generally sparingly soluble in water but dissolve in common polar aprotic solvents such as DMF, DMSO, and chlorinated solvents (DCM, chloroform). Researchers should verify solubility empirically for their specific formulation needs.

Stability: The compound should be stored in a cool, dry environment away from light and moisture. The diketone moiety can be sensitive to strong nucleophiles and reducing agents; aryl bromide bonds are stable under ambient conditions but reactive under palladium- or nickel-catalyzed cross-coupling conditions.

Safety: As with most brominated aromatic compounds, standard laboratory precautions apply: use in a well-ventilated fume hood, wear appropriate PPE (gloves, lab coat, eye protection), and consult the Safety Data Sheet (SDS) before use. Specific hazard classifications should be confirmed from the product SDS.

Research and Synthetic Applications

Cross-coupling chemistry: The two aryl bromide sites are ideal handles for palladium-catalyzed reactions such as Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig couplings. These transformations allow systematic extension of the π-conjugated system or introduction of heteroatom-containing arms, enabling access to a wide library of functionalized phenanthrenequinone derivatives.

Condensation reactions: The ortho-diketone unit reacts readily with 1,2-diamines to form quinoxaline-fused ring systems, a widely used strategy in constructing electron-deficient heterocyclic frameworks for n-type organic semiconductors and OLED emitter layers.

Luminescent and electronic materials: Phenanthrenequinone-based structures and their ring-fused derivatives have been investigated as components of organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and photovoltaic devices. The 3,6-dibromo substitution pattern provides symmetry and pre-organized reactive sites for constructing larger conjugated architectures.

Ordering, Storage, and Quality

Availability: 3,6-Dibromophenanthrene-9,10-dione is available from Aladdin Scientific under SKU D290447. For current pricing, available pack sizes, and stock status, please visit the product page or contact our sales team.

Purity and specification: Research-grade reagents from Aladdin Scientific are supplied with a certificate of analysis (CoA). Researchers requiring high-purity material for device fabrication or analytical reference purposes should confirm purity specifications on the CoA or contact technical support.

Storage recommendations: Store in a sealed container at room temperature or as specified on the CoA, in a cool, dry, dark location. Avoid prolonged exposure to air and moisture to maintain compound integrity over time.

Frequently asked questions

What is 3,6-Dibromophenanthrene-9,10-dione used for in research?

It is primarily used as a bifunctional building block in organic synthesis. The aryl bromide groups enable palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Sonogashira), while the ortho-diketone readily undergoes condensation with diamines to form quinoxaline-based ring systems. These features make it valuable for constructing π-conjugated materials for OLEDs, OFETs, and related organic electronic devices.

How should 3,6-Dibromophenanthrene-9,10-dione be stored to ensure stability?

The compound should be stored in a tightly sealed container in a cool, dry, and dark location to prevent degradation from moisture, light, and air. Consult the certificate of analysis (CoA) supplied with your specific lot for any additional storage conditions. Following these guidelines will help maintain purity and reactivity over the product's shelf life.

What solvents are suitable for dissolving 3,6-Dibromophenanthrene-9,10-dione?

Phenanthrenequinone derivatives are generally poorly soluble in water but dissolve in polar aprotic solvents such as DMF and DMSO, as well as in chlorinated solvents like dichloromethane (DCM) and chloroform. Researchers should empirically test solubility under their specific conditions, as actual solubility can vary with temperature and concentration.

Does the 3,6-dibromo substitution pattern affect the compound's reactivity compared to the unsubstituted phenanthrene-9,10-dione?

Yes. The bromine substituents at the 3- and 6-positions introduce additional electron-withdrawing character to the aromatic system and, importantly, provide two discrete sites for metal-catalyzed cross-coupling. This enables stepwise or simultaneous functionalization to build complex, extended conjugated architectures that are inaccessible from the parent unsubstituted phenanthrene-9,10-dione.

Where can I purchase 3,6-Dibromophenanthrene-9,10-dione from Aladdin Scientific?

You can order 3,6-Dibromophenanthrene-9,10-dione directly from Aladdin Scientific under product SKU D290447. Visit the Aladdin Scientific website to check current stock, available pack sizes, and pricing, or contact our customer service or sales team for bulk inquiries and quotations.

References

1. General reference: phenanthrenequinone chemistry and applications in organic electronics. Specific literature to be confirmed by subject-matter expert.
2. Lumtec / Da Ran Chemical product reference: K0404 (internal supplier designation for 3,6-Dibromophenanthrene-9,10-dione). Source: product description field.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.