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1-Bromonaphthalene

1-Bromonaphthalene is an organic compound with the formula C<sub>10</sub>H<sub>7</sub>Br. 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:

C<sub>10</sub>H<sub>8</sub> + Br<sub>2</sub> → C<sub>10</sub>H<sub>7</sub>Br + HBr

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 organolithium 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 (1.656-1.659<sub>nD</sub>), 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.

See also

References