2-Bromo-9H-xanthen-9-one CAS 56341-31-2 98% Off White Solid OLED Intermediate Pharmaceutical Building Block

1. Product Overview

2-Bromo-9H-xanthen-9-one, commonly referred to as 2-Bromoxanthone (CAS 56341-31-2), is a brominated derivative of xanthene-9-one with the molecular formula C₁₃H₇BrO₂ and a molecular weight of 275.10. This compound features a rigid, planar tricyclic structure consisting of two benzene rings fused to a central oxygen-containing heterocycle with a carbonyl group. It typically presents as an off-white solid with a melting point around 150°C. The presence of the bromine atom at the 2-position provides a versatile handle for further synthetic elaboration via transition-metal-catalyzed cross-coupling reactions or nucleophilic aromatic substitution. Supplied at a guaranteed purity of 98%, it serves as a crucial building block in the development of advanced organic electronic materials and bioactive pharmaceutical compounds.

2. Key Features and Advantages

• High Purity Standard: Minimum 98% assay ensures batch-to-batch consistency for sensitive photophysical and biological assays.

• Reactive Bromine Site: The C-Br bond facilitates efficient Suzuki, Heck, and Sonogashira couplings, enabling the rapid construction of complex biaryl or conjugated systems.

• Planar Conjugated Core: The rigid xanthone scaffold promotes strong π-π stacking and efficient charge transport, vital for high-performance OLED devices.

• Excellent Thermal Stability: High melting point and robust molecular framework allow for processing at elevated temperatures without decomposition.

• Morphological Advantage: Supplied as a free-flowing off-white solid, simplifying accurate weighing and handling in both laboratory and pilot-scale syntheses.

• Dual Application Profile: Effectively bridges the gap between pharmaceutical scaffold design and functional material science.

3. Main Applications

• OLED Intermediates: Used as a core precursor for synthesizing blue-emitting fluorophores and host materials. It is often employed to build larger conjugated systems with tuned HOMO/LUMO levels for improved device efficiency and stability.

• Pharmaceutical Building Block: Serves as a key intermediate in the synthesis of xanthone-based natural products and analogs. These derivatives are investigated for their potential antimicrobial, anticancer, and anti-inflammatory activities.

• Photovoltaic Materials: Incorporated into the backbone of organic semiconductors for organic photovoltaics (OPVs) and dye-sensitized solar cells (DSSCs) to enhance light absorption and charge carrier mobility.

• Fluorescent Probes: Utilized in the development of chemosensors and bioimaging probes due to the inherent fluorescence of the xanthone chromophore.

• Organic Synthesis: Acts as a versatile electrophile in the synthesis of ligands for catalysis and as a precursor for heterocyclic compounds in academic research.

4. Technical Specifications

5. Storage and Handling

Store in a tightly sealed container in a cool, dry, and well-ventilated area protected from light. Stable under recommended storage conditions. Avoid exposure to moisture and high temperatures. Handle in a well-ventilated area or fume hood to minimize inhalation of dust. Wear appropriate personal protective equipment (PPE), including safety goggles, nitrile gloves, and a laboratory coat. Prevent dust generation during transfer. Keep away from incompatible materials such as strong oxidizing agents and strong bases. Wash hands thoroughly after handling. For long-term storage, refrigeration (2-8°C) is recommended to maintain optimal stability, though room temperature storage is acceptable if kept dry and dark.

6. Safety Overview

This substance may cause irritation to the skin, eyes, and respiratory tract. Signal Word: Warning. Hazard Statements: H315 - Causes skin irritation; H319 - Causes serious eye irritation; H335 - May cause respiratory irritation. Precautionary Statements: P261 - Avoid breathing dust/fume/mist; P264 - Wash skin thoroughly after handling; P271 - Use only outdoors or in a well-ventilated area; P280 - Wear protective gloves/protective clothing/eye protection/face protection; P302+P352 - IF ON SKIN: Wash with plenty of soap and water; P305+P351+P338 - IF IN EYES: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing; P312 - Call a poison center/doctor if you feel unwell; P332+P313 - If skin irritation occurs: Get medical advice/attention; P337+P313 - If eye irritation persists: Get medical advice/attention; P362 - Take off contaminated clothing and wash before reuse; P403+P233 - Store in a well-ventilated place; keep container tightly closed; P501 - Dispose of contents/container in accordance with local/regional regulations. In case of contact, rinse affected area with copious water. Seek medical attention if irritation persists. Always refer to the latest Safety Data Sheet (SDS) before use.