NINGBO INNO PHARMCHEM CO.,LTD. is dedicated to providing essential chemical building blocks that fuel scientific advancement. Among these, 2,6-Dibromoanthraquinone (CAS 633-70-5) stands out due to its crucial role in various advanced chemical syntheses. This article delves into the fundamental properties and common synthetic routes of this significant brominated anthraquinone derivative, offering a clearer understanding of its value.

Physical Properties:
2,6-Dibromoanthraquinone typically presents as a yellow to orange crystalline powder. Its molecular formula is C₁₄H₆Br₂O₂, with a molecular weight of approximately 366.01 g/mol. It exhibits a high melting point, generally around 290-295°C, indicative of its stable crystalline structure. While largely insoluble in water, it demonstrates solubility in hot organic solvents such as DMF (dimethylformamide) and DMSO (dimethyl sulfoxide), which is important for its processing and reaction capabilities.

Chemical Structure and Reactivity:
The molecule consists of an anthraquinone core substituted with two bromine atoms at the 2 and 6 positions. This specific substitution pattern significantly influences its electronic properties, rendering the anthraquinone ring system electron-deficient. The carbonyl groups at the 9 and 10 positions contribute to its overall electron deficiency and reactivity. The bromine atoms are key reactive handles, readily participating in various cross-coupling reactions (e.g., Suzuki, Sonogashira) and nucleophilic substitutions. This reactivity is what makes it an invaluable intermediate for further chemical modifications.

Synthesis Methods:
The synthesis of 2,6-Dibromoanthraquinone commonly involves the bromination of anthraquinone or its derivatives. One prevalent method utilizes 2,6-diaminoanthraquinone as a starting material. Through a process involving diazotization followed by bromination using reagents like tert-butyl nitrite and copper(II) bromide in acetonitrile, high yields of 2,6-Dibromoanthraquinone can be achieved under controlled conditions. The optimization of reaction parameters, including temperature, solvent, and reagent stoichiometry, is crucial for maximizing yield and purity. Alternative methods may involve direct bromination of anthraquinone under specific catalytic conditions.

Applications:
The primary applications of 2,6-Dibromoanthraquinone lie in its use as a vital intermediate. It is extensively employed in the synthesis of high-value dyes and pigments, contributing to excellent colorfastness and performance. In the realm of materials science, it serves as a precursor for advanced organic electronic materials, including semiconductors for OLEDs and organic solar cells, as well as photoactive compounds. Its potential as a pharmaceutical intermediate, particularly in the development of anticancer agents, is also an area of growing interest.

NINGBO INNO PHARMCHEM CO.,LTD. is committed to providing high-purity 2,6-Dibromoanthraquinone to researchers and manufacturers worldwide. Our consistent quality ensures reliable performance in your synthetic endeavors, supporting innovation across diverse chemical industries.