1-Bromonaphthalene


1-Bromonaphthalene is an organic compound with the formula C10H7Br. It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid.

Synthesis and reactions

It is prepared by treatment of naphthalene with bromine:
The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile. It forms a Grignard reagent and organolithiuim compound. 1-Lithionaphthalene can be further lithiated to give 1,8-dilithionaphthalene, a precursor to peri-naphthalene compounds.

Applications

Because of its high refractive index, 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.
The compound is also used as a precursor to various substituted derivatives of naphthalene.