9-Bromoanthracene, with the CAS number 1564-64-3, is an important organic compound. It is a crystalline solid with a specific molecular formula of C₁₄H₉Br. Its molecular weight is approximately 257.12 g/mol. The substance typically has a melting point around 100 - 104 °C, which makes it relatively stable under normal storage conditions. The compound is insoluble in water but shows solubility in common organic solvents such as benzene, toluene, and chloroform. These solubility properties are crucial as they determine its compatibility with different reaction systems and industrial processes.
9-Bromoanthracene has a wide range of applications in various fields. In the field of organic synthesis, it serves as a key intermediate. It can be used to introduce the anthracene moiety into other molecules through substitution or coupling reactions. This is particularly useful in the synthesis of complex organic compounds with potential biological activities, such as pharmaceuticals and agrochemicals. In the area of materials science, 9-Bromoanthracene is used in the preparation of organic semiconductors. These semiconductors are essential components in organic light - emitting diodes (OLEDs), organic field - effect transistors (OFETs), and other optoelectronic devices. Its unique chemical structure allows it to contribute to the charge - carrier mobility and photophysical properties of the resulting materials.
When using 9-Bromoanthracene, proper handling procedures must be followed. First, it should be stored in a cool, dry place away from direct sunlight and sources of ignition. Before use, ensure that all equipment is clean and dry to prevent contamination. When weighing the compound, use appropriate laboratory weighing equipment in a well - ventilated area. For reactions, it is often dissolved in a suitable organic solvent. The reaction conditions, such as temperature, pressure, and reaction time, need to be carefully controlled according to the specific reaction requirements. It is also important to use appropriate protective equipment, including gloves, goggles, and a lab coat, to avoid direct contact with the compound, as it may be harmful if inhaled, swallowed, or in contact with the skin.
Caso 1: Síntesis farmacéutica
In the synthesis of a novel anti - cancer drug, 9-Bromoanthracene was used as a starting material. The reaction involved a palladium - catalyzed coupling reaction with an aryl boronic acid. First, 9-Bromoanthracene was dissolved in toluene along with the boronic acid and a palladium catalyst. The reaction mixture was heated to reflux for several hours under an inert atmosphere. After purification by column chromatography, the desired product was obtained with a good yield. This new compound showed promising anti - cancer activity in in - vitro cell tests.
Case 2: Organic Semiconductor Preparation
For the preparation of an organic semiconductor for OLEDs, 9-Bromoanthracene was reacted with a specific amine compound. The reaction was carried out in a high - boiling - point solvent under strictly controlled temperature and pressure conditions. The resulting product was then spin - coated onto a substrate to form a thin film. The thin film exhibited excellent hole - transporting properties, which significantly improved the efficiency and performance of the OLED device.
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