9Bromoanthracene

9-Bromoanthracene is an organobromine derivative of the polycyclic aromatic hydrocarbon anthracene, formed by substitution of a bromine atom at the 9-position of the fused ring system. Its chemical formula is C14H9Br, and its molecular weight is approximately 257.1 g/mol. The molecule features a bromine substituent on the central ring, with the remaining structure retaining the planar, rigid anthracene framework.

Physical properties commonly described for 9-bromoanthracene include its appearance as a solid at room temperature and its general insolubility in water. It is typically soluble in many nonpolar or moderately polar organic solvents, such as chlorinated solvents and aromatic hydrocarbons. The compound is relatively stable under typical laboratory conditions when kept away from strong oxidants and excessive light exposure.

Synthesis and occurrence in literature: 9-bromoanthracene is prepared by electrophilic bromination of anthracene. Under suitable conditions, bromination can be directed to the 9-position, yielding the 9-bromo isomer preferentially. It is used as a versatile synthetic building block due to the reactivity of the aryl–Br bond in cross-coupling reactions.

Applications: The compound serves as a starting material or intermediate in organic synthesis, particularly in cross-coupling methodologies such as Suzuki, Negishi, or Kumada couplings. This enables the installation of various aryl or vinyl groups at the 9-position, facilitating access to 9-substituted or extended anthracene derivatives for use in dyes, organic electronics, and materials chemistry.

Safety: Like many organobromine compounds, 9-bromoanthracene can be an irritant to skin, eyes, and the respiratory tract. It should be handled in a well-ventilated area with appropriate personal protective equipment and disposed of according to applicable regulations.