2Bromonaphthalene

2-Bromonaphthalene is an organic compound with the chemical formula C10H7Br. It is a derivative of naphthalene, where one of the hydrogen atoms on the second position of the naphthalene ring has been replaced by a bromine atom. It appears as a solid at room temperature and is generally insoluble in water but soluble in many organic solvents.

The synthesis of 2-bromonaphthalene can be achieved through various bromination reactions of naphthalene. One common method involves the direct bromination of naphthalene using a brominating agent like bromine in the presence of a catalyst. Control over reaction conditions is important to favor substitution at the 2-position over other possible positions. Alternative synthetic routes may involve Sandmeyer-type reactions on 2-aminonaphthalene.

2-Bromonaphthalene serves as a valuable intermediate in organic synthesis. Its bromine atom can be readily displaced or modified through reactions such as nucleophilic substitution, Grignard reagent formation, or palladium-catalyzed cross-coupling reactions like Suzuki or Heck couplings. These reactions allow for the introduction of various functional groups and the construction of more complex molecules, including dyes, pharmaceuticals, and materials with specific electronic or optical properties. Its derivatives are explored for applications in organic electronics and as fluorescent probes.